Tony D'Andrea Assassinated

Tony D’Andrea got his start in the dark corners and alleys of the Levee. Through hard work, muscle, and not a little violence, he rose to become Chicago’s leading Italian politician. He met his end in the bloodiest political feud in the city’s history, shot to death on the front steps of his home here at 902 S. Ashland Ave.

Born in Sicily in 1872, D’Andrea showed an early gift for languages, and graduated at the University of Palermo before making his way to the United States in 1896. He disembarked at Buffalo, New York, then found his way down to Baltimore, where he entered St. Mary’s Academy, a seminary where he trained for the priesthood. After three years at St. Mary’s, and with additional training at St. Bonaventura’s Academy in Allegheny, Pennsylvania, D’Andrea was appointed to a pastorship at St. Anthony’s Italian Catholic Church on the far south side of Chicago in June, 1899.

The clerical collar fit poorly. Six weeks after his appointment, D’Andrea fell in love with a woman, Lena Wagner, who he met in the barbershop of a friend on W. Grand Ave. The two eloped to Milwaukee and married there. D’Andrea was subsequently excommunicated from the church, and maintained a distant relationship to Roman Catholicism throughout the rest of his life. At his death, he was refused a church funeral.

(Pictured: Antonio D'Andrea, dressed in clerical uniform in 1899)

After leaving the priesthood, D’Andrea became a private language tutor, and also held part ownership in a macaroni factory in a warehouse district on the South side. To be close to the factory, he settled with his new wife in an apartment at 2125 S. Archer Ave., in what is today Chinatown. At the time, Mayor Carter Harrison was leading a political attack on the old Custom House Place red light district, and so this formerly-quiet neighborhood where the D’Andreas lived was quickly growing into the city’s premier red light district, soon to be known throughout the world as “the Levee”.

Around the same time, another couple, future mob-founder Jim Colosimo and his young wife Victoria Moresco, opened the New Brighton brothel just a block north on Archer Ave., and the Everleigh Sisters opened their famed house of ill-repute a block north of that. Criminal enterprise surrounded the D’Andreas, and the underworld opportunities were endless.

While vice was the preferred get-rich-quick scheme for those around him, D’Andrea’s religious leanings may have disinclined him from such pursuits. Instead, he took up counterfeiting.

Around 1900, D’Andrea traveled to New York, and there purchased a large quantity of phony dimes. It’s a testament to subsequent inflation that counterfeiting such small currency could have been profitable, but at the time, a dime could buy two “tubs” of beer at Michael Kenna’s Workingmen’s Exchange saloon.

The Secret Service, today best known for their work protecting the President, was originally established as an agency of the Treasury Department, tasked with investigating counterfeiters. In 1902, Capt. Thomas I. Porter of the Secret Service literally “followed the money” directly to a macaroni factory on the south side of Chicago, where he went undercover as a state tax agent to gain D’Andrea’s confidence. After he had collected sufficient evidence to prosecute, a squad of Secret Service agents and Chicago police arrived at the D’Andrea home on Archer with arrest warrants. While Mr. D’Andrea was being taken into custody, Mrs. D’Andrea, looking a little fuller-figured than usual, attempted to leave the house through the back exit. Captain Porter commanded an officer to stop her, at which point a bag full of counterfeit specie fell out from under her dress and scattered across the floor. The jig was up.

D’Andrea had little choice but to plead guilty, and federal prosecutors offered a deal by which he could avoid jail in return for turning state’s witness against the men who sold him the counterfeits. D’Andrea was taken to New York state to testify at their trial, but upon arrival, he refused to testify. Likely word had gotten to him that his life was in danger if he opened his mouth on the stand. Without D’Andrea’s testimony, that case failed, and the deal to save him from prison was off. In April, 1903, Antonio D’Andrea entered Joliet prison (the federal government at the time frequently placed criminals in state facilities), where he served 13 months.

It is an indication that D’Andrea already had powerful friends in the Chicago Italian community that, at the end of his prison sentence, he received a “civil pardon” from President Theodore Roosevelt, which restored his civil rights, though it did not clear his record or spare him from serving any of his time.

There is some evidence that, after release, D’Andrea continued activity in the counterfeit money racket for some time, but he certainly continued building his language tutor and macaroni-production businesses, both of which were successful. He was also able to help his Sicilian family come to Chicago, and several of his brothers and nephews also became successful. His brother Joseph D’Andrea became involved in organized labor, and rose to become president of Sewer and Tunnel Miners’ Union Local #4. In those days, as today, there were severe battles between unions, frequently organized along ethnic lines, for major work contracts. Joseph D’Andrea was involved in just such a struggle over the West Side site where Union Station was then under construction, and he was shot and killed there under mysterious circumstances in the fall of 1914.

He may have been the victim of some agent of a rival union, or his death may have been from a disgruntled member of his own union. Joseph D’Andrea had organized a system by which laborers had to pay $5 in dues to the union every time they took a new job; given the level of turnover in the construction industry, this was a frequent occurrence, and a source of some bitterness among the rank-and-file. In any case, upon his death, his brother, now going by the Americanized name “Anthony” to distinguish himself from his former life as “Antonio”, took over the presidency of the largely Italian union, a position he used to propel himself into politics. Through his work with the union, he also became close friends with “Diamond Joe” Esposito, who was working as a business agent for the sewer and tunnel miners, and who would one day also become an important political and underworld figure in Chicago.

By this time, Tony D’Andrea and his wife had moved from the Levee district into the Little Italy neighborhood, located in the 19th ward, taking up residence at 745 S. Halsted St. In 1914, he first dipped his toe into Chicago politics, running for county commissioner as a Democrat. Though he lost the race, his was clearly a political star on the rise. The following year, he was appointed the ward leader for Democrat Robert Sweitzer's 1915 mayoral campaign. In a bruising primary against the incumbent, Carter Harrison, Sweitzer emerged victorious, with a large margin of victory among Italian voters in the 19th ward. Sweitzer was ultimately defeated in the general election by Republican William Hale Thompson (the last Republican mayor of Chicago), but 19th ward alderman John “Johnny De Pow” Powers, who had led the Harrison campaign in the ward, began to see D’Andrea as an important political rival.

Powers, an Irishman representing an increasingly Italian constituency, was an astute tactician, and offered his support to D’Andrea for various political offices (other than alderman), including county commissioner. But the ex-priest had his eyes on a bigger prize, and in 1916, he ran for alderman from the 19th ward. In those days, each ward had two aldermen, with staggered terms. In 1916, Powers’ acolyte in the 19th, James Bowler, was up for re-election, and the Democratic primary battle between Bowler and D’Andrea promised to be fierce. Bowler had Ald. Powers on his side, and D’Andrea was supported by Rocco de Stefano, a close confidant of vice-magnate and Levee heavyweight “Big Jim” Colosimo.

February, 1916 found D’Andrea courting votes among the ward’s residents. In one case, he volunteered to be a character witness in court for a fellow Sicilian who was seeking naturalization. When the Superior Court clerk sought to verify D’Andrea’s own citizenship, however, he looked under “D” instead of “A”, and when he found nothing in the state’s records, suspicions began to circulate that the aldermanic candidate was not a U.S. citizen. This led others to dig into D’Andrea’s past, where they uncovered the case of a very similar-looking man, also named D’Andrea, an defrocked priest who had served 13 months at Joliet for counterfeiting.

The news hit the papers, and Ald. Bowler hired Pinkerton detectives to investigate D’Andrea’s past. They quickly surmised that Anthony D’Andrea, the labor leader and pillar of the Italian community, and Antonio D’Andrea, the passer of phony dimes, were one and the same man. Speaking to reporters the next day, D’Andrea admitted as much, but offered a stirring – if not quite believable – defense:

The facts were that when a counterfeiter was trailed by the government official to my house and placed some counterfeit money in our pantry during my absence, Mrs. D’Andrea, a most lovable and charitable woman, in order to remove the stain of suspicion from the sacredness of her own home and family, discovered that in some inconceivable manner the money was hidden in her pantry, took it out for the purpose of reporting her findings to me, and to remove the odium of guilt from my happy and cheerful home.

In the meantime, as she was about to leave the house, the government officials arrested her and kept her in custody for many hours, before I was allowed to see my wife, who had already become a human wreck from anguish, sorrow, and disgrace. With the most profound love for her and with the hope that not a stain should be placed against her character nor the character of our little girl, and with the promise that if I took the blame, my wife would be liberated, under the most inscrutable circumstances that could be imagined, and with the promise that if I gave to the government officials information regarding the gang of counterfeiters and plotters that I would be released, I remained silent, so as to shield them who had already threatened my life and that of my family if I spoke.

As a result of which I was forced to keep within my bosom the secret which, if exposed, would mean my immediate death, and I became a victim of the most unparalleled conviction that was ever had in the federal court.

At the time, it was pointed out that an Illinois statute forbade anyone convicted of a felony of holding public office, but D’Andrea’s civil pardon from Pres. Roosevelt apparently allowed him to remain in the race, though he was now scandal-ridden. Essentially the only quality that recommended D’Andrea to the office was the fact that he was an Italian, running in a ward that was, by this time, almost 80% Italian residents.

Thus, D’Andrea and his supporters took it personally when some of their fellow countrymen failed to support him. And some of D’Andrea’s supporters were rather violent men, including the Genna family, who in a few years would spill innumerable gallons of blood while running the city’s bootleg distillery business. On the evening of February 21, 1916, Frank Lombardi, an Italian immigrant and a major supporter of Ald. Bowler, was in the saloon he ran on Taylor street when two friends arrived. The three men raised their glasses in a toast, and at that moment, one of Lombardi’s “friends” pulled a revolver and shot him in the gut, an injury he eventually died from.

Lombardi’s death further cast the pallor of the underworld over D’Andrea’s candidacy, and on March 1, with the votes counted, James Bowler defeated Anthony D’Andrea, 4,163 votes to 1,753. D’Andrea was disappointed, but he had only just begun to fight. There would be many more opportunities to come.

D’Andrea focused on continuing to build support among the ward’s Italian residents, making his headquarters on Taylor Street the “Italian-American Educational Club”. He also became president of the Unione Siciliana, the chief social and political organization of Sicilians in Chicago; future leaders of the organization include such criminal luminaries as Angelo Genna, Sam “Samoots” Amatuna, Antonio Lombardo, and Joe Aiello. D’Andrea’s business and political success is reflected in the fact that he was able to purchase a large home at 902 S. Ashland Ave., where he lived with his wife on the second floor, and rented out the first floor.

In 1919, D’Andrea ran to be a delegate to a constitutional convention in Illinois to be held in 1920. When the votes were counted, the official record on the night of the election showed D’Andrea had lost by 82 votes; however, a later recount showed D’Andrea the victor. A court inquiry into the election turned up substantial evidence of fraud, with many of the additional so-called “voters” having not actually voted, or in the great Chicago tradition, having died years earlier. The extra votes were thrown out, and D’Andrea was again the loser.

Nevertheless, D’Andrea was still considered an important political figure in the district. So much so, in fact, that in order to dissuade him from running for alderman against him in 1921, Ald. Powers supported D’Andrea for the position of ward committeeman, a position that held at least as much, if not more, power than the aldermanship itself. In April, 1920, with Powers’ help, D’Andrea was elected to the position; however, voter irregularities again sandbagged the count, and a court threw out the results.

At this point, as described in this post, Ald. Powers dramatically recanted his support for D’Andrea, and chose to fill the ward committeeman position himself. Soon after, Powers’ home was the target of a bombing. As the incident suggests, D’Andrea and his supporters were increasingly turning from away from the ballot and towards violence. In 1921 D’Andrea announced he would run against Powers in the next aldermanic election, and the campaign between the two was the bloodiest in Chicago history, with dirty tricks and intimidation on both sides.

In February, a bomb exploded outside a D’Andrea rally near Blue Island and Taylor. When reporters approached D’Andrea, he practically admitted a role in the earlier bombing of Powers’ home:

I wouldn’t care if they threw a bomb at my house. That’s all in the game, and it wouldn’t hurt any one else but me. But to throw one into a meeting where there are a lot of workingmen, that’s another thing.

In retaliation for the bombing, D’Andrea’s supporters, which likely included the wildest of the Genna clan, Angelo Genna, and Sam Amatuna, organized a violent hit on two Italian precinct captains for Powers, as described in this post. Election day was a complete fiasco, with kidnappings of election workers, and widespread violence and intimidation of voters, but at the end of the day, the old “gray wolf,” John Powers had defeated his rival by the narrow margin of 381 votes.

With another lost election, D’Andrea declared “I’m through with Nineteenth Ward politics for good.” Asked for comment, Ald. Powers sarcastically replied, “Very magnanimous of him, I’m sure.”

But D’Andrea’s word was accurate. His political life was at an end – if only because the rest of his life was, too. D’Andrea had taken to carrying a pistol with him everywhere, and had been arrested for carrying a concealed weapon on several occasions; the violence associated with the election had likely warned him he was a marked man.

On the evening of May 10, 1921, he was out late, enjoying dinner with his old friend and political compatriot, “Diamond Joe” Esposito, at a local Italian restaurant. At 2:00 a.m., his bodyguard and driver, Joseph Laspisa, dropped him off in front of his home at 902 S. Ashland, and sped off, while D’Andrea climbed the stairs to his second-floor apartment. The first floor apartment was empty at the time, though the D’Andreas had hired decorators to paint and refurnish the flat for rental. The previous residents of the first floor had left at the beginning of the month, after receiving a threatening note, indicating that D’Andrea’s rivals were planning to dynamite the building.

In any case, the first floor apartment was unoccupied, but there had been some activity there all afternoon, which the neighbors attributed to the decorators. But no decorators had been on the site that day. As D’Andrea climbed the steps of his building, a sawed-off shotgun peaked through the window from the first floor, and fired off seven shots, five of which hit their mark. D’Andrea reached for his pistol and fired back, but quickly collapsed on the steps as his assassin escaped out the back and into a waiting car in the alley. Hearing the shots, Mrs. D’Andrea arose from bed and hurried down to where her wounded husband lay. “Lena, Lena, I’m dying, I’m dying,” he cried out to the woman he had left the church for.

(Pictured: Illustration of D'Andrea's home on S. Ashland Ave., where he was shot)

When police arrived, they found two clues in the first-floor apartment assassins’ nest: a soft brown hat, size 7, with the initials “S.P.” inscribed inside, and a $20 bill in the hat band, along with a card reading “For Flowers”. Police also found a handprint in some freshly laid paint, presumably left by the killer.

Suspicions immediately turned to Ald. Powers and his supporters, although Powers disowned the killing: “I do not believe it was politics. D’Andrea has had a good deal of trouble and it hasn’t been all political. He has been mixed up in labor matters and there may be some race feud back of it.”

Asked for comment, “Diamond Joe” Esposito, D’Andrea’s dinner companion that night and also a political figure in the ward simply responded, “So they shot him, eh?” Political violence had made killings in the 19th a fact of life.

D’Andrea hung on to life for a few days in the hospital, but finally succumbed on May 12. Refused a church burial due to his excommunication in 1899, a service was held on the steps of his home on Ashland Ave., right where he was shot, and 8,000 attended, flooding the street with people for three blocks around.

The bloodletting in the 19th did not, however, end with D’Andrea’s death. Ten days later, Michael Licari, a D’Andrea partisan, was murdered, and the following month, Joseph Laspisa, D’Andrea’s bodyguard and his driver on the night of his death, was killed while driving down Oak St. in Little Sicily, near "Death Corner", shot by a back seat passenger. Eventually, over 30 murders were attributed to the Powers/D’Andrea fight, most of them, including D'Andrea's, never solved.

The dream of an Italian alderman to represent Little Italy also died with D’Andrea that night. In July, 1921, with pressure from Ald. Powers, the 19th ward was redrawn and broken up into parts of the 20th, 25th, 26th, and 27th wards, none of which had an Italian majority.

After his death, the Genna brothers took over D’Andrea’s political headquarters and turned his political bailiwick into the massively dispersed distilling organization that supplied a large portion of the illegal liquor in Chicago during Prohibition. Several of D’Andrea’s relatives were closely involved with the Gennas and their partners in bootlegging, the Torrio-Capone organization. One nephew, also named Anthony D’Andrea, was Capone’s manager for his Depression-era soup kitchen on S. State st. Later, he became the president of the powerful hod-carriers union, and was a defendant in a federal antitrust case in the 1940s, accused of restraining the use of ready-mix concrete in Chicago, which would have eliminated a large number of union jobs.

Another nephew, Philip D’Andrea, got his start as a bodyguard for Al Capone, and was later a key member of The Outfit, the mob organization constituted of Capone’s men, after Capone went to prison in 1931. Philip D’Andrea served three years in prison in the 1940s on charges of extortion, along with Outfit luminaries Paul “The Waiter” Ricca, Louis “Little New York” Campagna, and Charles “Cherry Nose” Gioe.

D’Andrea’s home at 902 S. Ashland stood into the 1980s, when it was demolished to make way for the University of Illinois at Chicago’s Molecular Biology Research Building, completed in 1995. The building is notable for a large staircase inside that mirrors the shape of a double helix.

Dillinger’s Plastic Surgery on Pulaski Rd. (or Crawford Ave.?)

By the end of May, 1934, John Dillinger was hiding out in Chicago. Having robbed innumerable banks and broken out of jails twice during the last 12 months, he had become an internationally-known superstar criminal. Besides local and state authorities, almost the entirety of the newly-formed Division of Investigation (later, the FBI) was involved in efforts to hunt him down, dead or alive (but better dead). As “Public Enemy #1”, it was increasingly difficult to find friendly (or unsuspecting) help in evading the law. Dillinger knew he couldn’t continue dodging J. Edgar Hoover’s agents forever; drastic measures were necessary. The great bank robber’s most desperate attempt to evade capture took place here, at 2509 N. Crawford Ave. (now Pulaski Rd.), where he went under the knife to permanently change the face everyone in America now recognized.

January of 1934 saw most of the Dillinger gang wintering in Tuscon, Arizona, on the lam from a serious bank job in East Chicago, Indiana, where Dillinger himself is believed to have killed a police officer. Caught by local police, the famous criminal was extradited to Indiana and placed in jail at Crown Point, Indiana. It was there that he first hired Louis P. Piquett, a Chicago attorney known for close ties to the Chicago mob organization known as the “Outfit,” the remainder of Al Capone’s organization. Probably Piquett’s name was familiar among the crowd Dillinger ran with, or it may be that Piquett offered his services at a cut rate for this high-profile defense. Other have suggested that Dillinger was in some loose way connected with the Outfit, and may have met Piquett previously.

In any case, Piquett, who had no formal legal training but had passed the Illinois bar, became Dillinger’s counsel and best source of assistance after he broke out of Crown Point in March, 1934. Piquett’s presence may have been what drew Dillinger back to Chicago, instead of hiding out in his native Indiana or escaping into the Far West. Piquett’s law office on Wacker Drive was a common meeting place for the Dillinger Gang, although Piquett always denied that Dillinger hid out there while a fugitive.

It was Piquett and his co-counsel, Arthur O’Leary, who connected Dillinger with the makeshift operating room on Crawford Ave. In April, Piquett approached a low-level crook and bar owner, James “Cabaret” Probasco, about finding trained surgeons willing to perform the operation. Probasco, then in his 60s, had been a boxer and a liveryman in his youth and was trained in veterinary science. He had also been a major part of a serious diamond theft ring in the 1920s, serving as the main “fence” for stolen jewels. In 1924, his own wife, Clara, had testified against him to police, probably because her husband’s partner-in-crime was also his mistress, Florence. Despite Clara’s testimony, the case against Probasco fizzled thanks to the work of his attorney Louis Piquett, and he walked on charges of possession and sale of stolen property. Divorcing Clara, he remarried Florence, and went into the tavern business, opening up shop in Rogers’ Park, on Howard St. near Rogers Ave.

(Pictured: James Probasco)

When Piquett approached Probasco about helping his new client, John Dillinger, dollar signs flashed in Probasco’s eyes. He told Piquett he could find the surgical talent and the location, but for a high price, $5,000 (over $80,000 in today’s dollars). It took some convincing by O’Leary, but Dillinger finally agreed to the proposal, and went to work in early May, robbing banks to “earn” the fee.

To perform the surgery, Probasco looked for men with medical training, but who were also acquainted with the underworld. In Dr. William Loeser, he found his man. Loeser, a German immigrant, had trained at Northwestern University and ran a successful surgical practice until his arrest for violation of the Harrison Anti-Narcotic Act of 1914, the first federal law restricting the manufacture and sale of cocaine and heroin in the U.S. Dr. Loeser was paroled in 1932, at which point he fled to Mexico, where he developed a technique to remove fingerprints, becoming his own first patient for the procedure, which involved acid treatment.

(Pictured: Dr. William Loeser)

To assist Dr. Loeser, Probasco found another surgeon, Dr. Harold Cassidy, who had a less shady past, but who was unable to pass up the opportunity to make a quick buck. Probasco promised $1,700 to Dr. Loeser and $1,200 to Dr. Cassidy. All that was left was to find an operating room. Legitimate hospitals were obviously out of the question, and neither of the two doctors was willing to use his own offices. Instead, Probasco opted for the least expensive option – his own apartment at 2509 N. Crawford Ave. Probasco’s wife and former jewel thief, Florence, had died young the year before, and he was currently living with a girlfriend, Margaret Doyle, but he felt she could be misled about the operation. So, on the evening of May 27, John Dillinger arrived at Probasco’s home and prepared for surgery the next day. Dillinger handed Probasco $3,000 in cash up front, with the remaining $2,000 to be paid after the operation.

The following evening, Piquett’s assistant Arthur O’Leary picked up the two doctors, and drove them to Probasco’s home, where they instructed Dillinger to remove his shirt and lie down in the bedroom. Dr. Loeser offered Dillinger the option of a local or a general anesthetic, and Dillinger chose the latter. While Loeser washed his hands in an adjoining bathroom, Dr. Cassidy administered the ether. Suddenly, Dr. Cassidy began yelling for help. Returning to the bedroom, Loeser saw that Dillinger had received too much anesthetic too quickly, and was choking on his own tongue. Quickly, Loeser located his forecepts and freed the blocked airways, saving Dillinger’s life.

But after that experience, Dillinger decided on the local anesthetic, which meant he was largely awake and in excruciating pain, for most of the procedure. For several hours, the two doctors removed a mole from his forehead, a dimple from his cheek, and changed shape of face, smoothing out the famous cleft in his chin, and erasing the seams in his cheeks using implanted kangaroo tendons. They also employed Loeser’s acid method to burn out his fingerprints.

(Pictured: Probasco's home at 2509 N. Crawford Ave. (now Pulaski Rd.) with a crowd of curiosity-seekers outside after Dillinger's death).

With the surgery a success, Dillinger returned to Probasco’s home on June 3, this time bringing with him a fellow gang member, Homer Van Meter, who also went under Drs. Loeser and Cassidy’s knives. Over time, however, Dillinger became unsatisfied with the operation. The science of plastic surgery was still in its infancy, the two doctors were not leading experts, and the circumstances under which they operated were primitive. Thus, Dillinger was still completely recognizable. After his death at the hands of Division of Investigation and East Chicago police officers (see this post for further details), an autopsy found identifying traces of his fingerprints remained, despite Dr. Loeser’s best efforts.

Anna Sage, the famed “woman in red” (she actually wore orange and white, but appeared to be in red under the glare of the Biograph Theater marquee) who turned in Dillinger to the feds, was most likely also the source of their information about James Probasco. A few days after Dillinger’s death on July 22, 1934, J. Edgar Hoover’s men picked up Probasco and took him for questioning to their offices on the 19th floor of the Banker’s Building at Clark and Adams streets. In a search of his apartment, agents found the evidence of the surgery: sleeping potions, acids, gauze, surgical scissors, and cotton were still in the medicine cabinet (likely, Probasco expected more work from other members of the Dillinger Gang).

Agents no doubt questioned Probasco intensely for hours, seeking information on Dillinger companions such as Van Meter and Baby Face Nelson, who were still at large. On July 24, lead investigator Melvin Purvis left Chicago for Washington to brief J. Edgar Hoover about Dillinger’s death and the continued investigations, leaving agent Samuel Crowley in charge of the work in Chicago. Crowley was known as a tougher interrogator than Purvis, and was willing to bend the rules (or worse) to get information out of suspects. In a case a year earlier, agents in the very same room where Probasco was being held, had dangled a mob suspect out the window by his ankles, 19 floors off the ground, in an attempt to make him talk.

In any case, July 26, 1934 saw James Probasco under questioning at the Bankers’ Building, and mysteriously, just a few minutes after agents left him alone in the interrogation room, Probasco stepped up from a chair to the window sill in the room, three feet off the ground, and leapt out the window, falling to his death on the pavement below. Because of the reputation of his interrogators, there has always been a strong suspicion that Probasco did not defenestrate willingly – at worst, Probasco would have faced no more than 30 months in jail for harboring Dillinger, hardly a sentence worth dying over – but the coroner’s jury ultimately ruled the death a suicide. At the time of his death, Probasco held over $72,000 in life insurance policies, with his sister the chief beneficiary, but almost all of the payout was void in the case of suicide.

Nevertheless, the feds apparently got enough information to locate Dr. Loeser, who turned state’s witness against Dr. Cassidy and attorney Louis Piquette. Piquett went on trial in a widely covered case for harboring a fugitive – Dillinger – but was ultimately found not guilty. Unfazed, prosecutors immediately put Piquett on trial for harboring Homer van Meter, using Piquett’s testimony at the Dillinger trial to trap him into contradictions on the stand. In 1936, Piquett was found guilty and sentenced to two years in federal prison. He was also fined $10,000 and disbarred in Illinois. In 1950, President Harry S Truman pardoned Piquett, and he applied for reinstatement to the bar, but died before a decision was made in 1951.

As a reward for his part in the prosecution of Piquett, Dr. Loeser was sentenced to only one day in prison for his crime. However, he also had to serve 18 additional months for leaving the country after his parole in the narcotics case. Dr. Cassidy received only probation, and served honorably in the army medical corps during World War II; however, after the war, however, he had a nervous breakdown and committed suicide in 1946.

Probasco’s apartment building at 2509 N. Crawford was demolished, and an extension was built from the building next door into the lot, numbered 2511 N. Pulaski. Even the name of the street has changed; within Chicago city limits, Crawford is now known as Pulaski Rd. The story of the name change is an interesting one.

On October 1, 1933, while Dillinger was languishing in jail in Lima, Ohio (from which he would soon be freed at the hands of his gang), Cook County civil service commissioner and former president of the Polish Women’s Alliance of America, Miss A. Emily Napieralski, appeared before Mayor Edward J. Kelly, petitioning him to support a change in name for Crawford Ave. to recognize the bravery of Polish general and American Revolutionary War hero Casimir Pulaski. Poles have a long history in Chicago -- Napieralski’s family had arrived as pioneers in the 1830s – and the 1930s saw their political influence growing. Miss Napieralski told the Tribune,

My purpose is to bring about a closer brotherhood of man. Count Pulaski came to America and offered his services to George Washington. In giving distinguished service in the revolutionary war he lifted himself above any particular nationality, and his name should be remembered by all.

Neither Mayor Kelly nor the city aldermen wanted to be seen as anti-Polish, so there was strong support on the city council for the proposal. Understandably and unsurprisingly, however, businesses along Crawford Ave. were nearly uniformly opposed. They had spent heavily advertising their addresses, investments which would be lost if the name change was granted. Some businesses, such as Crawford Laundry and Crawford Grill, would clearly face serious problems.

Also opposed were grandchildren of Peter Crawford, the pioneer Chicago farmer for whom the street was named. Crawford had arrived in Chicago in 1844, and, for $15/acre, purchased the plot of land now bounded by Pulaski Rd., Kostner Rd., Cermak Rd., and 26th Street; his farmhouse home was at what is now 2230 S. Pulaski Rd. Crawford was one of the founders of the township of Cicero in 1857, and as early as 1863, the dirt path abutting the east side of his property, connecting Ogden and Archer Aves., was known as Crawford Ave. Chicago city street signs indicating the name of the street were posted in 1913. At the 1933 meeting of the city council where the name change was under consideration, Crawford’s grandchildren, John H. Crawford and Nettie Ferenson appeared, along with Chicago Historical Society leader Edward P. Brennan, who argued

“We have no Bowling Green, as has New York, no Commons, as has Boston; no Independence Hall, as has Philadelphia. All of our landmarks were wiped out by the fire. All we have left of historical significance is names, and the Historical Society is opposing the wiping out of the names of the families which helped build Chicago.”

Nevertheless, in December, 1933, the city council approved the name change to Pulaski Rd. by a vote of 34-12, rejecting compromises offered by the Crawford business group, such as renaming Augusta Blvd. in honor of Pulaski. You might expect that the business group would be bitter over the loss, but you probably wouldn’t expect them to wage an intense fight over the street’s name for the next 18 years, which in fact they did.

The Crawford business owners first took the city to court, arguing that over 75% of the owners of property along the street opposed the name change, and that the council’s actions flew in the face of Illinois’ home-rule precedent, by which decisions were localized to the greatest degree possible. The group won a temporary injunction in January, 1934, but an appeals court eventually sided with the city, and “Pulaski Rd.” street signs began to be erected in the summer of 1934. Most of these were immediately stolen by upset property owners.

The Crawford business group did not give up so easily, however. For three years, they continuously lobbied state lawmakers in Springfield, and in 1937, they got their wish: a state law was passed indicating that if the deed-holders of 60% of the frontage on any street petitioned city government to change the name of that street, their petition would be granted.

Polish groups that supported Pulaski Road immediately saw the implications and devised an ingenious solution. They found a tiny one-block street, Haussen Court, on the north side, where the majority of the property owners were of Polish descent, and petitioned the city to change the name of that street to Crawford. In doing so, they would effectively block any attempt to revert Pulaski Rd. to the name Crawford, since that would cause duplication in street names.

Mrs. Eda Haussen Bartels, an elderly lady who lived on one corner of Haussen Ct., and after whose father, pioneer farmer Fred Haussen, the street was named, was blindsided by the new plan and vigorously opposed it. The following year, in 1938, she passed away, and her physician loudly told the newspapers that her death “probably” resulted from worry about the name of her street.

The city corporation counsel took both petitions – for changing Pulaski back to Crawford, and for changing Haussen to Crawford – under advisement, and undertook a painstaking and lengthy survey of property on both streets to learn the precise boundaries of each owner’s lot. In 1939, the city announced the failure of both petitions. Pulaski Rd. had 147,207 feet of frontage within Chicago city limits, and the Crawford business group’s petition was short by 9,727 feet. Similarly, the Haussen Ct. petition would require 1,264 feet of frontage to pass, but was short by 90 feet.

The Crawford business group immediately went back to work, and managed to find additional Pulaski Rd. frontage property owners, more than enough to push them over the 60% mark, but the city refused to accept the supplementary petition, causing a return to court for all parties.

During this time, most Chicagoans continued to refer to Pulaski Rd. as Crawford Ave., despite the change. In 1944, a streetcar conductor who called out “Crawford” was attacked by a Polish rider, Michael Orzschkwsk, who grabbed him by the collar and threw him to the ground, yelling invective in Polish (a sympathetic court fined Orzschkwsk $1 and ordered him to pay the conductor’s tailoring bill).

The advent of World War II put the Crawford-Pulaski debate on hold for a few years. Nevertheless, the animosity between the groups was never far below the surface. A rather nasty 1945 letter to the editor in the Tribune, signed “Old Timer,” was symptomatic:

The wailing that is going on among the Polish groups of Chicago with regard to the establishment of the Curzon line as the eastern boundary of Poland arouses little sympathy among thousands of Chicago people who recall that these same Poles have made no move to restore Crawford avenue to the American public since they unlawfully annexed it in 1933 and changed its name to Pulaski road.

In 1950, the Crawford business group again sued the city, indicating they had a petition signed by owners of 60.4% of all the owners of Pulaski Rd. frontage supporting a return to the Crawford name. They asked the court to force the city to follow the 1937 state law. In 1951, Superior Court judge John Sbarbaro did just that, and so, after 18 years, Pulaski Rd. became once again Crawford Ave.

An intense battle between the two sides then took place, with Polish groups who supported the Pulaski name attempting to lure or threaten Crawford Ave. business owners to withdraw their names from the petition. The petitioners responded by pressuring these property owners to remain on the petition. Several petition signers filed withdrawals, and then withdrawals-of-withdrawals over the next year.

However, the return to Crawford Ave. was short-lived. On appeal in November, 1952, the Illinois Supreme Court ruled that the 1937 state law creating the 60% margin for a street name change was unconstitutional, reversing Sbarbaro’s ruling, and handing the property right to street names back to the city council, which swiftly ordered Crawford Ave. to once again become Pulaski Rd., the name it holds to this day. Outside of the city limits, however, such as in Lincolnwood and Skokie, the continuation of Pulaski Rd. is still marked as Crawford Ave.

Nathan Leopold's Home

In general, I’m not much interested in serial murderers or “thrill” killers. But you can’t have a website about the history of crime in Chicago without some mention of Nathan Leopold, one half of the famous Leopold and Loeb duo, whose atrocious murder of 14-year old neighbor Robert Franks in 1924 captured the morbid fascination of newspaper readers throughout the world. Leopold, son of a shipping and paper magnate, lived in the mansion at 4754 S. Greenwood Ave., in the South Kenwood neighborhood.

After the Great Fire, the Kenwood neighborhood became home to many of the city’s business and cultural elite, desirable for its proximity to the Loop, the meatpacking district (the Armours and Swifts were residents), and the University of Chicago. The home at 4754 S. Greenwood was built in 1886 by Charles B. Van Kirk, one of the founders of the Chicago Board of Trade. After World War I, Kenwood’s tree-lined boulevards became especially attractive to wealthy Chicago Jews, including Nathan F. Leopold, Sr. Leopold, Sr.'s parents, Samuel and Babette, had emigrated to the U.S. from Germany after the failed revolution of 1848 in that country, settling first in Michigan, where Nathan was born. After the Civil War, the Leopold family moved to Chicago, and young Nathan Leopold, Sr. went into the business of organizing the burgeoning shipping business through the Great Lakes. He first found success as a principal founder of the firm Leopold & Austrian, but he later started several other businesses, including the Manitou Shipping Company and a copper mining interest in Michigan. Later, he became a major player in paper mills as well, forming the Fiber Can Corporation, and operating a paper mill at suburban Morris, Illinois.

Leopold was active in the community, serving as president of the Young Mens’ Hebrew Association in Chicago, forerunner of the modern Jewish Community Center organization. In 1892, he married into one of the city’s wealthiest Jewish families, taking Florence Foreman as his wife. Foreman’s father, Gerhart, was a Chicago pioneer, and one of the city’s earliest bankers; her sister later became Mrs. Julius Rosenwald. The Leopolds had three children: Foreman, Samuel, and Nathan, Jr.

Nathan F. Leopold, Jr., was born in 1904, and was early recognized for intellectual brilliance, as well as his cruel mind. Fascinated by birds throughout his life, Leopold’s nurse was horrified by the callousness the boy showed towards birds, killing them for specimens in his collection. Ironically nicknamed “babe” by his family and friends, no expenditure was spared in the young scholar’s education, and after high school, he attended the nearby University of Chicago and the University of Michigan, becoming the youngest graduate in the history of the U of C at age 19 in 1923. In the fall of 1923, Leopold re-enrolled at the University, seeking a degree from the Law School.

It was in November of that year that he began plotting a perfect murder with friend Richard “Dickie” Loeb, another child savant who had graduated at the University of Michigan the previous year at age 18, and was then enrolled in a masters’ degree program in History at the University of Chicago. Years of speculation by researchers about whether Leopold or Loeb originally hatched the murder plan have never turned definitive, but Leopold’s cruelty and lack of conscience, and Loeb’s fascination with crime and detective stories mean it easily could have been either. Both were students of epicurean and nihilist philosophies, with Leopold a master of medieval erotic literature and an avowed atheist.

(Pictured: Nathan F. Leopold, Jr.)

In any case, for adventure and thrills, the two first hatched a plan to kidnap the son of a wealthy Chicago family for ransom, puzzling for months over the question of how to collect the ransom without capture. Finally, they pieced together a complex and daring plan. The father of the kidnapped boy would be directed by taxicab to a 63rd street drug store, where he would receive a telephone call telling him to immediately catch a southbound train from the nearby station, presumably before police could be notified. On the train, he was to find a note telling him to throw the bag containing the money from the train at a certain point between two stations, where Leopold and Loeb would be waiting to receive the loot.

The kidnapping and murder itself were no less carefully planned. Leopold planned to rent an automobile, by which the victim would be spirited away. However, then as now, rental service companies demanded reliable credit before allowing a borrower the keys. Leopold filled out an application at the car rental company under a false name (“Martin D. Ballard”), and indicated employment with a certain Mr. Mason, giving a work telephone number associated with a local lunch counter. When the rental company checked on the number, Loeb jumped out of his seat at the restaurant and picked up the phone before the waitress could reach it, confirming that he was “Mr. Mason,” and yes, Mr. Ballard certainly did work for him – and was one of his best employees.

(Pictured: The rented Willys-Knight car used for the kidnapping)

With the maroon-colored Willys-Knight car, purposely chosen as the same model as Leopold’s own vehicle, in their possession, Leopold and Loeb agreed on an alibi if questioned. The two agreed that after classes on Wednesday, May 21, 1924, they would say they went to the north end of Lincoln Park to look for a particular bird Leopold was hunting, a heron-gull. Their story would continue with the two drinking gin and wine in the park, with the younger Loeb becoming mildly drunk. Since Loeb’s family disapproved of alcohol, the two would claim they went to dinner at a Kenwood tavern, the Cocoanut Grove, at 53rd and Ellis Ave., afterwards cruising around Washington Park, picking up two girls they met and taking them to the Jackson Park golf course. Eventually, they would claim, the two returned to Leopold’s home on Greenwood at 11:00 p.m., with Loeb returning home at 2:00 a.m. after his family was asleep, to sleep off the day’s drinking.

With their story straight, Leopold and Loeb drove around the neighborhood on the afternoon of the 21st, looking for a victim. At the Harvard School, a private primary school for wealthy children on Ellis Ave., just around the corner from Leopold's home, Loeb spotted a family friend, 14-year old Robert “Bobby” Franks, who had been umpiring a youth baseball game at the school’s sporting field. Loeb and Franks were not close friends, but they had frequently played tennis together, so Franks came over to the car at once when Loeb called to him, “Hello, Bob! Come in a minute, I want to ask you about a tennis racket.”

Bobby Franks entered the car, sealing his doom. Later at trial, Loeb would claim that he was driving while Leopold delivered the fateful blow to the victim in the back seat; Leopold claimed the opposite, and it was never determined who actually killed Franks. In any case, a taped-up chisel blow to the head rendered Franks unconscious just minutes after he got in the car, and a gag placed in his mouth quickly suffocated him. Leopold and Loeb drove around for around four hours afterwards, waiting for dusk, then dumped Franks’ body in what was then a sparsely-populated prairie and lagoon area, near the Pennsylvania railroad tracks at 119th Street.

The two then returned to Kenwood, parking the car near Leopold’s house, and burned their blood-stained clothes in Loeb’s basement. They played cards until late that night.

The next day, they telephoned the Franks home, making a ransom demand for $10,000, and also had a ransom note delivered, which had been prepared before the kidnapping and addressed on the way home from the murder. On the phone, Leopold, referring to himself as “George Johnson,” threatened to kill the boy if the Franks family contacted police. Of course, Bobby Franks was already dead, and the family did in fact contact police, but the police chose not to file a formal report immediately in order to keep the supposed kidnappers in the dark while detectives followed up leads.

Thus, without a police report of the kidnapping, when Franks’ body was discovered by a railroad worker the day after the killing, he was not immediately identified. The unidentified boy was found naked except for his eyeglasses, strewn a few feet away in the mud, and one stocking. The railroad man who found him placed the glasses back on his face and called for backup in moving him to the morgue.

Meanwhile, at the Franks home, the murdered boy’s father was waiting at his home for the taxicab Leopold and Loeb had arranged to take him to the drug store near the train station, from which he would depart and throw the ransom money out of the window. Just before the taxi arrived, however, word came by telephone: Bobby Franks had been identified as the likely identity of a boy's body found near the railroad tracks. Instead of following the ransom note’s demands, the Franks family drove to the morgue, where they sadly confirmed that it was, in fact, their boy. Just one thing was wrong: whose eyeglasses were those? Bobby Franks had perfect eyesight and never wore glasses.

Hence, the famous clue that would finally break the case.

Leopold had dropped the glasses, which he wore only rarely, at the crime scene, and hadn’t noticed it until later. The police found the optician who had sold the glasses, Almer Coe & Co., and asked them to search their sales records, a task which was simplified by the fact that this particular pair employed a rare type of hinge, produced only by the Bobrow Optical Company in Brooklyn, New York. This fact narrowed the list of suspects to just three in the Chicago area, one of whom was Nathan F. Leopold, Jr., of 4754 S. Greenwood Ave., just a few blocks from the Franks home. The attention of the police, which had initially focused on various teachers at the Harvard School where Franks attended, and a suspicious druggist who had recently attempted suicide, turned completely to Leopold.

In the early morning of May 30, 1924, Leopold was brought into State Attorney Robert Crowe’s office for interrogation by Crowe and Chief of Detectives Michael Hughes. Questioned about the location where the body was found, Leopold answered confidently, “Yes, I have been there fifty times. You see, I am interested in ornithology [study of birds]. I frequently go there with classes and with companions.”

Shown the glasses, he denied they belonged to him, but admitted he owned a similar pair. Detectives were even then searching his home, where they found an empty Almer Coe & Co. glasses case, but no spectacles. Confronted with this evidence, State’s Attorney Crowe asked Leopold whether it was possible he had lost his glasses at the scene of the crime.

“I told you I had been there frequently. I believe I was there either the Friday or the Saturday just before the murder. I might have dropped them on that occasion,” replied Leopold.

But had the glasses lain in the dirt for a week, as Leopold claimed, they would have been covered with dirt and streaked with rain, when in fact they were found completely clean. Next, Crowe showed Leopold the ransom note, which had been published in the newspapers during the past week. “This letter was written by an educated man. Do you think that you could have written such a letter?”

“Yes, I could easily duplicate it, if I couldn’t write a better one. There is one mistake in the letter. The word kidnapping is spelled kidnaping. I noticed it at the time.” Likely, Leopold had purposely misspelled the word to mislead investigators.

Police detectives searched Leopold’s home, and found his typewriter, but it was not of the sort that was used to create the note. Leopold confidently repeated the alibi he and Loeb had agreed upon, describing their travels to Lincoln Park to look for birds, the drinking, the girls they met in Washington Park, and so on. When questioned, Loeb first claimed he was too drunk to remember the events of the day, but eventually foggily repeated a story similar to Leopold's. The police began to believe that Leopold was in fact innocent, the victim of an unusual and coincidental set of circumstances. During 30 hours of questioning, Leopold held court with detectives and reporters, demonstrating his superior intellect on any subject proposed. Claiming that his heroes were Oscar Wilde, Nietzsche, and Epicurus, he was asked, “What about Socrates?” “I never thought a lot of that old bird,” Leopold rakishly replied.

Police very nearly released him. Finally, however, someone thought to question the Leopolds’ chauffeur, Sven Englund, who lived in the family’s garage. When asked about Leopold’s maroon Willys-Knight, Englund indicated that it had been in the garage all day. Englund’s wife confirmed seeing it at home – and thus, not in Lincoln Park, not at the Cocoanut Grove Inn, not cruising around with two boy geniuses and their new girlfriends, and not at the Jackson Park golf course. When confronted with Englund’s statement, Loeb was the first to crack. He demanded to speak with Crowe and District Attorney John Sbarbaro, and began confessing the true story of the murder.

When told that Loeb was confessing, Leopold realized the jig was up and admitted his role in the killing. In a chilling statement related later to reporters, the young nihilist told one officer, “If I’d have only known that Loeb was preaching [confessing], if I’d known that I would have killed myself there in my room. Do you recall when I was standing at my desk? I had my hand on my gun. But before I killed myself I’d have put a few policemen out of the way. Yes, I’d have got you.”

Over the next two days, while housed in separate rooms at the Windermere Hotel on 56th and Hyde Park Blvd. (which still stands next door to my former dormitory, the Broadview), Leopold and Loeb led detectives around the south side of Chicago, pointing out precisely where they had disposed of Franks’ clothes, as well as the typewriter used in the ransom note, a second machine owned by Leopold, which he had dumped into the Jackson Park lagoon after the murder. A few days later, divers would find the typewriter, essentially closing the case on the two killers.

An early notion to plead not guilty on defense of insanity was quickly rejected by their counsel, world-famous attorney Clarence Darrow (who had defended the indefensible in Chicago before). The boys were too intelligent for anyone to believe they didn’t understand the difference between right and wrong, the M'Naughten Rule standard for insanity accepted in Illinois. Instead, Darrow convinced the boys and their families to plead guilty, and try to avoid the death penalty. A hearing before a judge began in late August, 1924, and concluded on September 10. Primarily on the basis of their age, the judge in the case denied the state’s motion to impose the death penalty, instead imposing sentence of life plus 99 years on each. Both were assigned to Joliet penitentiary.

Loeb, initially the more popular in prison, and the less aloof of the two, was murdered in the shower room in 1936 by a fellow prisoner who claimed Loeb had made homosexual advances toward him. Leopold served a minimum required third of his sentence and was released in 1958, living the rest of his life as a hospital worker in Puerto Rico, where he died in 1971.

The story of the two brilliant young murderers who killed for adventure and pleasure was irresistible to newspaper publishers throughout the world. Typical of the editorials was the Tribune, which asked rhetorically, “Were they bored by a life which left them nothing to be desired, no obstacles to overcome, no goal to attain? Were they jaded by the jazz-life of gin and girls, so that they needed so terrible a thing as murder to give them new thrills?”

The publicity was obviously difficult to handle for the families involved; curiosity-seekers gawked at them in front of their homes at all hours. After the trial, in October, 1924, Nathan Leopold, Sr., sold the home at 4754 Greenwood and moved to Lakeview, living on Roscoe St., near Belmont Harbor, where he died in 1929. His two other sons, Foreman and Samuel, changed their names to “Lebold,” continuing their father’s business and community interests until their retirements in the 1960s.

The Leopold mansion was destroyed in the late 1960s. The large home pictured at the top of this post was built on the site, but the photo below shows the home as it looked in the 1920s.

(Pictured: Nathan Leopold mansion, circa 1924)

Gangs of Chicago: Thomas "Buff" Higgins Leads the Wright Street Gang

By most accounts, 1893 was a banner year in Chicago. The World’s Fair exhibited the very best the city had to offer, including magnificent architecture, a harmonious blending of cultures, and a beautiful physical landscape, to millions of visitors. But in the shadow of the “white city” was a very dark city. Just a mile or two from the sparkling waters of Lake Michigan lay the Maxwell Street district, a neighborhood teeming with the most incorrigible criminals, young desperadoes scurrying through the filthy streets and rotting tenement buildings like vermin. Then as now, poverty and hopelessness bred desperation and hedonism, and young men with little to live for would die over even less. The most vicious of these men formed into street gangs which terrorized 14th Place, in those days known as either Wright Street). The leader of one of these gangs was Thomas “Buff” Higgins, who at age 23 was already a notorious figure and had been in and out of jail over 100 times. In the early morning of September 3, 1893, in a Peoria St. home, Higgins wrote the final chapter in his life in a frantic moment, igniting a city-wide debate on poverty, crime and punishment in Chicago.

“Buff” was a nickname, short for “Buffalo”, and possibly styled after the wild-west gunslinger star of countless dime novels, “Buffalo Bill”, whose human incarnation in William Cody had captivated Chicago in a series of performances at the World’s Fair that year. Born in Ireland in the early 1870s, Buff Higgins immigrated with his parents to Chicago at the age of 2. Like many of their countrymen, the Higgins settled in the Maxwell street district, where poor workingmen could afford a few square feet of space. Conditions in the neighborhood were poor, and it was no place to raise a family, but it beat starvation and religious strife in Ireland.

As a boy, Higgins attended the notorious Walsh School, which still exists today, where Irish schoolboys banded together against newer immigrant groups from Germany, Russia, Poland, and other Eastern European regions. Knives and even guns were commonplace in these schoolyard battles, and through them, Buff Higgins came to be an expert fighter; as the Tribune later described his upbringing, "Fighting came to him easily, and nature had given him a body well adapted for physical combat. Experience supplemented his natural ability as a fighter and it was not long before 'Buff' Higgins was a man to be feared by each and every one who happened to come into contact with him."

By age 14, Higgins had dropped out of school, and he descended into a life of crime, naturally falling in with some of the tough Irish street gangs that controlled 14th Place (then known as Wright St.), near the intersection of Sangamon Street, which was the location of so many battles with police that it became known as “Dead Man’s Corner”. Higgins’ first recorded arrest, at age 14, was for stealing grapes from a neighborhood fruit merchant. From that ignominious beginning, the following ten years saw Buff back in the city jail – or the “Bridewell”, as it was known – countless times for disorderly conduct, drunkenness, vagrancy, larceny, and assault. In 1891, Higgins was even implicated in the murder of a neighborhood laborer, George Scott, and the entire Wright Street Gang, in which he had become a chief member, was hauled into court.

Finally, in 1892, Higgins was sent to the state penitentiary at Joliet to serve a one-year prison sentence for robbery. When he finished his term in September, 1893, he returned to the neighborhood and shortly found himself in need of money. With two fellow members of his Wright Street Gang, Higgins planned a midnight robbery of an irresistible target.

(Pictured: Thomas "Buff" Higgins. The Tribune described him as "low browed and repulsive in features")

February of 1893 had seen the bankruptcy of one of the nation’s largest railroads, the Philadelphia and Reading, and other railroad companies were believed to be on the verge of collapse. Nowhere was the shock of these insolvencies greater than in Chicago, the heart of so many rail systems. In those days before federal deposit insurance, banks invested more conservatively, but were also more vulnerable to “runs” by depositors, who, hearing rumors of a bank collapse, all rushed to withdraw their savings, possibly exacerbating the feared collapse (see earlier posts here and here for more details on banking before FDIC).

Among those who withdrew their savings in cash during the “Panic of 1893”, as it was later called, was Mrs. Bridget McCooey, the wife of a Crane Bros. elevator factory laborer, and a resident of a hardscrabble working-class neighborhood west of the Loop, just north of “Bloody Maxwell”, where Higgins and company ran the streets. Mrs. McCooey withdrew the family’s life savings, around $400, and stored it in cash in their home at 153 Johnson St. (now 230 S. Peoria St., pictured above). Adjusting amounts for inflation over such long periods is difficult, since the quality and types of goods available for purchase have changed so tremendously (most people would rather have $1,000 to spend in the 2009 Best Buy catalog than $1,000 in the 1901 Sears catalog, even though the $1,000 in 1901 would in principle be “worth” much more than $1,000 in current dollars). Nevertheless, using ordinary measures of inflation, $400 in 1893 is the equivalent of around $10,000 in today’s dollars.

Perhaps Mrs. McCooey mentioned the withdrawal to a friend or neighbor, or perhaps a bank clerk had noted the unusually large withdrawal. In any case, word quickly spread around that a sizeable sum of cash was hidden somewhere in the McCooey home. Buff Higgins had found his target.

Around 2:00 a.m. on September 3, 1893, Higgins, joined by two fellow Wright Street Gang members, Harry “Sheeney Joe” Feinberg and Edward “Red” Gary, approached the McCooey home on Peoria St. The three men thoroughly rummaged through the home, overturning every cabinet and drawer, in search of the $400. Unknown to the robbers, Mrs. McCooey had decided a few days earlier that her bank was solvent, redepositing the cash they sought. Finally, there was only one place the trio had yet to look, the McCooeys' bedrooms.

Feinberg and Gary waited at the bedroom door, prepared for a quick getaway, while Higgins alone tiptoed into the bedroom of Bridget’s 42-year old husband, Peter. Higgins was opening a bureau drawer in the bedroom when he accidentally knocked over a chair, awakening the sleeping Mr. McCooey. What happened next would be replayed countless times in court. The Tribune describes the scene:

Springing to his elbow, half awake, [McCooey] was dazzled by the light of a lamp shining full in his eyes. The lamp was in the hands of a man who stood near the bed. Two other men were in the room near the door. A child would have known their errand -- robbery. As McCooey was in the very act of springing from his bed the man with the lamp flashed a revolver and fired. McCooey, checked in the midst of his spring, fell back beside his wife with a groan. The man with the pistol set the lamp on the floor and the three men ran out of the bedroom. Mrs. McCooey screamed her husband's name. He made no reply. She turned to him. His face and nightdress were covered with blood which was flowing from a wound in his left eye. Then she ran screaming from the house, crying: "Murder! They have killed my husband. Murder!"

A neighbor, awakened by Mrs. McCooey’s screams, ran the two blocks to the police station, and a squad of officers was sent out to search the slums for a killer. They knew it was more than likely that their murderer hailed from the Maxwell street district, so they began combing the streets around 14th Pl. and Sangamon carefully. At 5:00 a.m. four officers from the Maxwell Street Police Station were patrolling that infamous corner (another source says it was at 14th Place and Jefferson) when they heard a noise coming from the gutter below one of the vaulted sidewalks. The officers peered into the gutter and found Buff Higgins (apparently, Buff was one of the city’s clumsier criminals), lying on his back with revolver in hand.

Knowing Higgins had been released from Joliet just a few days earlier, and recognizing the robbery-gone-wrong as typical of the work of his ilk, the officers hauled Buff into the stationhouse for questioning. And it’s there that the writers of Higgins’ biography diverge regarding what happened next.

Under intense interrogation by police Captain Blettner, Higgins denied being a part of the crew that ransacked the McCooey home. Thinking he might react to the crime scene, officers brought Higgins back to the McCooey home, and had him face the forlorn family:

"Look at your work", scorned Capt. Blettner
"I did not do it, I do not know anything about it", replied Higgins, trembling.

Mrs. McCooey then rushed for Higgins, yelling "Is that the man who killed my husband? I shall kill him if he remains in my sight."

Officers subdued the distraught wife, but Higgins did not admit his guilt. Returning to the police station, however, under continued questioning, Higgins finally broke down and confessed, signing his name to a statement indicating he had committed the murder of Peter McCooey:

"I went in the house with two other men for the purpose of getting that $400 which I knew McCooey had. I was the first to go in, and the other two followed close behind. When we got inside we searched all the places where we thought the money might be, but we could not find it. I then went into the room where the man and his wife lay asleep and searched his clothes. There was only $1.65 in the pockets of his trousers. I was about to go out of the room when I made a noise which awoke the man. I saw him open his eyes and when he tried to get out of bed I fired the shot at him. I knew I hit him, because he groaned once and then all was still. The men with me heard the shot and jumped out of the window and ran away. I was not long in following, as I heard the man in the next room [a boarder at the McCooey home] getting out of bed. I went under the sidewalk at Jefferson and Fourteenth streets and staid there until the police arrested me."

Higgins’ own account of the confession, which he later gave in court, was quite different. In his version of the story, after returning from the McCooey home, the police stripped him naked and threw him into a basement cell at the stationhouse, where he remained for four days without food or drink. When he requested the presence of his attorney, A.J. Hanlon, the police refused. Finally, after four days, when Higgins was famished and devoid of all hope, the police captain appeared at his cell with a favorite Irish beverage, saying

"Buff, it is an outrage for you to be treated like this. You must be feeling pretty slim. Don't you want a bottle of whiskey?"

Higgins told the captain there was $0.50 in his clothes that he would happily trade for the liquor, and the captain complied, giving a bottle of whiskey to a man who hadn’t had a bite to eat in days. Buff Higgins was quickly in a state of delirious drunkenness. It was at this point, Higgins claimed, that the captain offered him his freedom. All he had to do was sign a statement declaring his innocence, and he would be free to go. Therefore, when the captain put a pen in Higgins’ hand, and pushed a sheet of paper in front of him, Buff was happy to sign, even though he was likely illiterate and had no attorney present.

In fact, the statement was a confession, and Buff Higgins had just signed away his life.
The police disputed this account, and claimed as evidence the fact that Higgins had similarly confessed to the coroner’s jury on the day after he signed his confession at the police station. But the Chicago police in those days were known for their brutal tactics, especially in crime-ridden immigrant wards like the Maxwell street district, so we cannot know for certain.

On November 29, 1893, just under three months after the crime took place, a jury returned a verdict of first-degree murder against Buff Higgins, and sentenced him to death. It was one of only three death sentences levied in Cook county that year. The others were against a Chinese laundryman, Junk Jack Lin, who allegedly murdered his cousin, and, far more famously, Patrick Prendergast, the assassin of Chicago mayor Carter Harrison. Prendergast was initially scheduled to meet the hangman’s noose on the same day as Higgins, March 23, 1894, a fact that sickened Higgins: Buff would be the first to admit he was a street gang member and a robber, but Prendergast was a lunatic. Higgins told a New York Times reporter, “When it comes my turn to shuffle off, I want Irish hemp and a green shroud [like Higgins, Prendergast was of Irish origin], but I draw the line on being compelled to pass out with Prendergast."

But Buff Higgins had one more ace up his sleeve. His attorney, A.J. Hanlon, petitioned the court for another trial based on new evidence, and on January 16, 1894, the court heard the motion. At this hearing, Higgins’ counsel placed into evidence the affidavit of one Joseph Kauper, an 18-year old neighbor of the McCooeys. Kauper’s affidavit indicated that he saw three men flee the McCooey home on the night of the crime, and that Buff Higgins was not one of them.

The prosecution in the case was stunned, but suspicious. Kauper was a dull boy (the Tribune indicated that “his answers to questions on the witness stand yesterday showed him to be dull of comprehension,” suggesting mild retardation), and why hadn’t he come forward with his story earlier? Under intense cross-examination at the hearing, Kauper broke down and admitted the affidavit was fraudulent. A friend of his, one Tim Collins, who was a politically-connected leader of a street-sweeping union, had apparently convinced him to sign the affidavit in order to “give Buff a lift”. Likely Higgins’ friends in the Wright Street Gang had put the screws to either Collins or Kauper -- or both -- to try to free Buff. But Kauper’s confession to perjury ended the last of Higgins’ hopes. "All right, I guess the jig's up with me now," he was heard to mutter in the courtroom after his motion for a new trial was denied.

Attorney Hanlon appealed to the Illinois Supreme Court for a stay of execution, which was denied on March 22. On hearing the news, the prisoner sighed,

Well, that's just what I expected. So my neck will crack Friday -- I'll hang. No use to tell me the Governor will interfere. Gov. Altgeld is out of the State. So is Lieut.-Gov. Gill, I understand...I haven't any money or influential friends behind me. Father Dore was with me this morning and gave me the consolation of the Catholic Church, of which I am a member.

In fact, Lieutenant Governor Joseph Gill did consider the case, but refused to interfere with the execution, and at noon on March 23, 1894, Buff Higgins was led onto the platform and a noose placed around his head. Prendergast’s execution had been stayed until July, so Higgins did receive one final wish, not to share the stage with the famed assassin.

Two Roman Catholic priests, including the aforementioned Father Dore, accompanied the Irishman in his last moments, placing a crucifix on his lips just before the hood was lowered over his head. The city’s newspapers delivered pages of purple prose describing the lurid death scene in the following day’s issue. Part of the Tribune’s description depicted the final moment for the terror of 14th Place: "Then there was a fall, as the rope stretched to its full tension with a sound like that from the heaviest string on the bass viol, 'Buff' Higgins had paid the penalty for murder."

Buff Higgins was only the third man executed in Cook County since the Haymarket defendants seven years earlier, but at least one hanging would take place every year in the county through the end of the decade. The rapidly-rising crime rates of the period inclined Chicagoans to take a sterner view regarding capital punishment. Perhaps the most remarkable fact of Higgins’ experience was the expediency with which his execution took place. Just three months passed between the crime and the conviction, and from thence it was less than another four months before all appeals were exhausted and the criminal was hanged. While capital punishment is still practiced in the U.S. today, the time between the crime and the execution typically stretches into decades. Even in Texas, the state where executions are most common, the average time between conviction and execution (not including time between the crime and the trial) is nearly 11 years. In California, the average prisoner under sentence of death waits 20 years before execution.

The last execution in Illinois took place in 1999. In 2000, then-Governor George Ryan (now federal inmate 16627-424) commuted the sentences of all prisoners then on death row after several were exonerated based on DNA evidence, suggesting widespread errors in policing and sentencing. Ryan’s successors in the governor’s office, Rod Blagojevich and Pat Quinn have maintained the moratorium.

Higgins' companions in the McCooey robbery eventually were caught. The police found Feinberg around the same time they arrested Higgins, while "Red" Gary managed to elude the law until 1895, when he was arrested for stealing the blanket off a horse. At his arraignment, he gave a false name, but an experienced detective recognized him. Both Feinberg and Gary served terms in jail for the robbery, and both continued criminal careers into the mid-1900s.

Peter McCooey’s home, pictured at the top of this post, is long gone, replaced by a condominium complex. The Maxwell Street slums where boys like Buff Higgins went bad is essentially gone, too, replaced largely by upscale condominiums and the University of Illinois at Chicago campus.

Death in the Barber's Chair: The Rise and Fall of Sam Amatuna

Unione Siciliana president Mike Merlo had kept the peace between rival alcohol-production organizations in Prohibition-era Chicago through his death in 1924. Over the next year, the violent war between the “Bloody” Genna brothers, operators of a gigantic dispersed distilling operation in Little Italy, and the Northside Gang headed by Dion O’Banion, heated up, and news of assassinations filled the city’s newspapers. Into this tinderbox stepped the dapper Don of the Maxwell Street district, Salvatore Samuzzo Amatuna (frequently known as Sam or even “Samoots”). As head of the powerful Unione, the young Amatuna struck a pose as a political kingmaker and gadabout in the Sicilian community, but he couldn’t bring peace to the underworld, and the bloody beer wars escalated until they claimed Amatuna himself as a victim, as he sat in a barbershop here, at 804 W. Roosevelt Rd.

Amatuna was born in the seafaring town of Pozzallo, Sicily, at the far south end of that island, in 1899. As a teenager, he found his way to Chicago, settling in the “Little Italy” district along Maxwell Street in the early 1910s. Like many young Sicilians in the neighborhood at the time, he found his calling in politics, providing the street-level muscle in the increasingly violent war over the aldermanic seat in the 19th ward, which included Little Italy. John Powers had held the seat since 1888, when the 19th was predominantly populated by Irish, but by the 1910s, Powers was presiding over an increasingly-Italian ward, and the new immigrants had their own rising political stars, including “Diamond Joe” Esposito and former Roman Catholic priest and convicted counterfeiter, Anthony D’Andrea.

D’Andrea ran against Powers’ right-hand man, James Bowler in the aldermanic election of 1916 (in those days, each ward had two aldermen), and the race was close, despite pre-election revelations about D’Andrea’s criminal past. Not all Italians in the 19th supported D’Andrea, however; Powers had made a career out of incorporating potential Italian rivals into his organization over the years. In fact, one of Bowler’s chief political advisors was a Sicilian, Frank Lombardi.

Nothing irked D’Andrea’s supporters more than the defection of Lombardi and other fellow countrymen – Italians constituted a substantial majority in the ward by that time, and easily could have elected one of their own, had they united behind D’Andrea. Just days before the election, Lombardi met two friends in a saloon on Taylor street. As the trio raised their glasses in a traditional Sicilian toast, one of the “friends” drew a .38 caliber revolver from his hip pocket and shot Lombardi dead.

The police advanced the theory that Lombardi was the victim of a “Black Hand” extortion scheme, a common occurrence among well-heeled Italians of the era, but Lombardi’s wife and just about everyone else blamed supporters of D’Andrea. The accusations among those in the know in Little Italy led directly to a hot-headed 17-year old from Sicily, Sam Amatuna.
Amatuna was questioned in Lombardi’s death, but with little evidence and most eyewitnesses unable to “remember” the scene accurately, no charges were ever filed. The murder may even have been counterproductive, as it revived voters’ recollections of D’Andrea’s sordid past, and
James Bowler won the election of 1916.

Regardless of his real guilt or innocence, Amatuna’s reputation as a man to be feared on Maxwell Street was established. Through his connections in D’Andrea’s organization, he also became a close ally of the Genna brothers, especially the toughest and most violent of that clan, Angelo. Both Angelo Genna and Sam Amatuna were fearsome characters in the district, but unlike Genna, Amatuna was able to separate business from social concerns, and when not cracking skulls for D’Andrea, he was widely known for his generosity and sunny personality, even gaining the moniker of “Smilin’ Sammy Samoots” in some quarters.

But behind the smile remained a man talented with a gun, and one fearless in using it for his own advancement. As one friend told reporters later, "Sure, if he wanted a guy knocked off, he'd have him knocked off, 'what the hell?' But he was a good guy just the same."

(Pictured: Sam "Samoots" Amatuna)

In 1921, D’Andrea again ran for alderman, this time directly challenging the incumbent Powers. Once again, D’Andrea relied on the force and violence doled out by toughs like Amatuna to help get out the vote, and once again, Italians supporting Powers were a major target (for his part, Powers was never afraid of dirty political tricks either). During May of that year, Paul Labriola and Harry Raimondi, lieutenants in the Powers organization, both met their ends at the hands of a five-man assassin crew, widely believed to have been headed by Angelo Genna and Sam Amatuna. Genna was arrested and put on trial, but walked when the prosecution’s lead witness changed his story on the last day before the jury convened.

Again, D’Andrea was unable to capture a seat on the city council, losing the election by 435 votes. Shortly after the election, D’Andrea was murdered, and the Genna brothers took over his organization, turning it from a political enterprise to a criminal one. With their base of Sicilian supporters, they produced massive quantities of (rot-gut) liquor in small stills in basement apartments throughout Little Italy, in the process becoming the key part in the supply chain that ended in the blind pigs and speakeasies run by Johnny Torrio and Al Capone. The Gennas employed Amatuna as the enforcer for their network of family-run microbreweries. It was “Smilin’ Sammy” who visited those who failed to meet their promised quotas of booze, and few suppliers fell behind the production schedule twice.

Violent and superstitious, the Gennas began butting heads with rival booze gangs, especially the Northside gang, run by the equally-superstitious singing-waiter-turned-florist, Dion O’Banion. O’Banion’s reckless hijacking of Genna deliveries, plus his general disrespect for his Italian competitors, made the blood of Angelo Genna and Sam Amatuna boil. The only factor keeping O’Banion from meeting the same fate as Lombardi, Labriola, and Raimondi, was the word of Mike Merlo, chief of the most powerful Sicilian social and political organization in the city, the Unione Siciliana.

But Merlo’s days were numbered. In 1924, he died of natural causes, and a few days later, O’Banion was dead in his floral shop, shot dead by three men, believed to include the Gennas' masterful assassins Scalisi and Anselmi, plus a third man, who the police believed to be either Angelo Genna or New York-based Unione president, Frankie Yale. When the police brought Yale in for questioning, it was Sam Amatuna who provided an alibi – Amatuna and Yale had been dining at the Palmer House hotel at the time, he claimed. No one was ever charged with the crime.

With the mediating influence of Merlo gone, the bullets flew in Chicago, and in the coming months, three Genna brothers met the same fate as O’Banion. Johnny Torrio was nearly assassinated as well, and he and the remaining Gennas fled the city.

Into the consequent void of power in Little Italy stepped Sam Amatuna. After Angelo’s death, he took two bodyguards and walked into the headquarters of the Unione Siciliana, informing everyone that he was now president. In his attempt at changing from a mere street tough to a powerful political force, he began acting the part of neighborhood Don, dressing in snappy clothes (it was said he owned 200 embroidered silk shirts – the newspapers repeatedly referred to him as the “Beau Brummel of Little Italy”) and buying haircuts and shaves for the teenagers hanging around the barbershop whenever he went in for a trim.

But make no mistake – under the silk shirt beat the cold heart of a killer. A story frequently passed around about Amatuna said that when a certain dry cleaners damaged his clothes, the enraged dandy retaliated by ripping out the stairs connecting the laundry from the street, and put a bullet through the head of the proprietor’s horse.

With the wealth he had amassed from his work with the Gennas, Sam Amatnua purchased a jazz club, the Bluebird Cafe, at Halsted and Taylor, for $40,0000, where he himself often performed, gaining a reputation as an excellent singer and violinist. He also acquired a beautiful home on Lexington Ave., near Damen Ave. (the street has since been vacated in that block). And most important of all, he was engaged to wed Miss Rose Pecaroro, sister to Mike Merlo’s widow. The marriage would make Amatuna peerless as a Sicilian community leader.

It was on a visit to the barber that Sam Amatuna met his end. On the evening of November 11, 1925, Amatuna walked into his favorite local barbershop at 804 W. Roosevelt Rd. He and Pecaroro were to see the opera Aida at 8:00 that evening at the Auditorium building on S. Michigan Ave. Isidor Paul, who had owned and operated the barbershop since 1918, threw a hot towel over Amatuna’s face and sharpened his razor. By coincidence, Amatuna was without his usual bodyguards that evening, and as a show of power, he never carried a gun personally any more.

At that moment, two olive-skinned men, one short and one tall, walked into the shop and drew guns. Paul screamed, and Amatuna jumped out of the barber’s chair, hiding behind it. The Tribune describes what happened next:

Two men walked in as he left the chair in which he had been shaved and massaged in preparation for an evening at the opera, and without waiting opened fire. Eight times their weapons cracked. One bullet took effect and Amatuna dropped: the others went wild as barbers and customers fell to the floor or ran for cover. Then the attackers backed out, ran to a car parked at the curb and escaped.

Two friends helped the bleeding Amatuna into a taxicab. Their first destination was not the hospital, but a cigar shop owned by Amatuna, around the corner at Taylor and Halsted Streets. There, Amatuna briefly met with his brother, Luigi, who had recently arrived from Sicily, likely informing him of the names of his attackers. From there, the trio left for the hospital.

For two days, doctors at Jefferson Park Hospital tried to revive Amatuna, but to no avail. With her planned elaborate wedding just weeks away, his bride was doubly stricken, and Amatuna agreed to a bedside ceremony in case he was unable to recover. With the physicians’ negative prognoses in mind, a priest was called and the arrangements made for just such an event. But before the ceremony could take place, Amatuna fell unconscious, and died at 2:00 a.m. on November 13.

As was customary for gangsters in his time, Amatuna’s funeral was lavish. At his fiancée, Rose Pecaroro’s home on the North side, $20,000 in flowers filled the home, the yard, and several neighbor’s yards. The casket was made of silver and cost a reputed $10,000. The funeral procession to Mt. Carmel cemetery, where Amatuna’s body was held in a vault for several days before being shipped back to Sicily, stretched for over a mile, snaking through the city past his home, his businesses, and stopping at the barbershop where he died – a visible indication of future retribution. At the gravesite, Luigi Amatuna threw himself on the coffin, beating his fists on it and swearing an oath of revenge in his native tongue.

(Pictured: The scene outside Amatuna fiancee, Rose Pecaroro's home, where Amatuna's funeral procession began)

Indeed, the bloodshed was far from over. Within a week, both of Amatuna’s absent bodyguards were killed – one of them on the way home from the funeral ceremony. Next in line for the presidency of the Unione Siciliana was Tony Lombardo, Al Capone’s personal friend. Lombardo was assassinated in the middle of the day at Madison and Dearborn Streets in the loop. The three succeeding Unione presidents, Pasqualino Lolordo, Joseph Giunta, and Joe Aiello met similar fates. The bloodshed of the 1920s sealed Chicago’s worldwide reputation as the country’s crime capital.

Who killed “Samoots”? The chief theory is that his death was merely another part of the spiraling bloodshed between the Genna-Torrio-Capone organization and the Northside gang. Most historians believe that Amatuna’s assassins were Vincent “Schemer” Drucci, one of the leaders of the Northside group, and Jim Doherty, a key member of the allied Westside O’Donnell gang. It appears Al Capone blamed Drucci and Doherty. A few months later, when Doherty and Assistant State’s Attorney William McSwiggin were seen drinking and gambling in Cicero at the Pony Inn, Capone ordered a hit on crew, in which McSwiggin died, a major factor in turning public opinion against Capone and raising his profile with Chicago police.

An plausibly, though less likely alternative theory is that Amatuna had fallen out with the Gennas in the months before his death, and that Capone ordered his murder in order to make way for his friend, Lombardo, to control the Unione and the Genna distillery network. In Chicago’s gangland, today’s allies frequently became tomorrow’s enemies, and vice-versa.

The barbershop where Amatuna met his fate continued in operation, run by Isidor Paul, until his retirement in 1956. Today, like much of the old Little Italy neighborhood, the building is gone, razed to make way for the facilities of the University of Illinois at Chicago. Until recently, the site was a baseball field for the UIC team, but is currently marked for the construction of a new condominium complex, Roosevelt Square.