Estelle Carey, Gangster Girlfriend, Murdered

On the afternoon of Feb. 2, 1943, residents of a quiet courtyard building in Lakeview at 512 W. Addison (pictured above) smelled smoke coming from the third-floor apartment where two female roommates, Estelle Carey and Maxine Buturff, lived. When firemen arrived on the scene, they were shocked to find Miss Carey dead, the victim of a brutal and bloody struggle involving a bread knife, rolling pin, iron, and a 10-inch blackjack club. Still alive after the beating, she had finally been doused in inflammable liquid and set afire. Who was Estelle Carey and why did she meet such a violent end?

Estelle Evelyn Smith was born in 1909 on Chicago’s northwest side. Her father died when she was two-and-a-half, and her destitute mother sent her to an orphanage, from which she did not return until 1916, when her mother remarried and took the name Carey. She attended school sporadically at Harriet Beecher Stowe school in Humboldt Park, finally dropping out to take work in a silk thread factory. Miss Carey was exceptionally beautiful, and she did modeling work on the side, before she became a telephone operator and then a waitress at a Northside restaurant. It was while working there that her life took a turn into the underworld.

(pictured: Estelle Carey)

Nicholas Deani Circella, often known as Nick Circella or Nick Dean, had come to the U.S. in 1902, and by the 1930s, was a nightclub owner associated with the Outfit, the group of criminals who inherited Al Capone’s organization. He was impressed with Carey’s beauty and offered her a raise to work in one of his clubs as a dice girl. She accepted and was installed at the Colony Club, 744 N. Rush St., where she specialized in “26”. In the game of 26, a pretty girl rolled a series of 10 dice; if the sum of the dice came to 26, the player won a free drink on the house.

Carey became very popular at the club, and when a high roller showed up, she was often called into work to assist. Not all of the dice games she ran were mere bar diversions like 26, though. One inveterate gambler at the club, who went by the name “Spinach,” claimed she had bilked him for $800 with a die which had the one-spot replaced by an extra five-spot. Other Colony regulars noted that Carey was especially skilled at switching dice with hidden loaded dice.

It was at one of Circella’s other clubs, the 100 Club on Superior, that a drunken Willie Bioff and George Browne stumbled into one night after extorting $20,000 from the Balaban and Katz theater chain, following up on the labor racketeering scheme begun by Tommy Maloy (who had, in turn, worked his way up in the Mossy Enright organization). When Browne spilled the beans about the scheme at the 100 Club, Nick Dean found out about it, and shared this priceless information with the Outfit brass. Together, Bioff, Browne, and Circella, with the backing of the Outfit’s muscle, went on to bilk millions from the major Hollywood studios.

Plenty of that money wound up in Estelle Carey’s closet, as Circella bought expensive jewelry and fur coats by the dozen for his girlfriend and employee. Police who searched Carey’s apartment after her murder said she owned no dress worth less than $150, the equivalent of $1,800 in today’s terms.

When Bioff got greedy, he and Browne and came under investigation and eventual indictment in 1941 by the IRS, and Nick Circella was sought as material witness. It was at this point that Circella and Carey fled into hiding together, with Carey dying her blonde hair black as a disguise. In May of that year, the Colony Club, run in absentia by one of Circella’s associates, was padlocked by Chicago police after evidence surfaced that more serious gambling than the 26 games took place behind the scenes there.

Circella was eventually apprehended in March, 1942, and sent to prison for six years.

Almost a year later, Estelle Carey was living in a quiet corner of Lakeview at 512 W. Addison, her hair now dyed red. On the day of Feb. 2, 1943, Carey’s roommate had left for work at 8:00 a.m., and nothing seemed amiss. At 1:00 that afternoon, Carey was having a conversation with her cousin on the telephone when the doorbell rang and her dog began barking. “The door bell’s ringing. I’ll have to go. Call me back in an hour,” she told her cousin.

She opened the door, recognizing her visitor, and invited him in. She went into the kitchen and poured powdered cocoa into two cups, following it with hot milk. When she had filled the first cup halfway, her visitor attacked her.

When Estelle Carey’s cousin called back at 2:30 p.m., there was no answer. About that time, Mrs. Jessie Lovrein, who lived in the ground-floor apartment below, saw a large man in a gray tweed overcoat descending the back stairs of the building, carrying with him two fur coats, turned inside out. Shortly after, the neighbors smelled smoke, and the fire department discovered the bloody scene just after 3:00.

Police immediately suspected a mob connection. Although the code of conduct among the Outfit prohibited violence towards wives and girlfriends, the Bioff-Browne incident threatened to take down the entire criminal organization, so desperation might have meant breaking the code. Virtually every known Outfit associate, including Tony “Joe Batters” Accardo, Sam Battaglia, Marshall Caifano, and others were questioned about the murder, but no leads panned out.

The police also considered other theories. When Circella’s wife, Ernestine, was questioned, she said

Yes, I knew her and I knew Nick was cheating, but I didn't know with whom. Show people are generally cheating on one another, but I wouldn't let it break up my home.

Did Estelle Carey know too much about the Hollywood extortion case, and was she killed to keep her quiet? Or was her death a powerful reminder to Circella, imprisoned at the time, about the dangers of turning state’s witness against his Outfit overlords? Or was her killer a disgruntled loser in one of the Colony Club’s gambling games? Was Estelle Carey killed by a jealous beau (of which she had many), or the wife or girlfriend of one of those beaus? Carey had been the “other woman” in a bruising 1938 divorce case involving a leading Chicago businessman, Earl Weymer, and Weymer admitted seeing Carey for dinner the three days before her death. Or was it all just a fur coat robbery gone wrong?

In favor of the last possibility, Carey’s death took place in the midst of a string of fur coat robberies on the Northside that year (14 during the previous four months, in which over 50 coats had been taken). When Carey’s roommate arrived home, she led police to a hidden compartment of a shoe bag, where Carey kept her most valuable jewelry. Had Estelle Carey refused to tell her attacker where the jewels were? But what kind of robber carries a can of gasoline with him, in case he needs to burn his victim? And why would Carey have let a stranger into her home and served him hot cocoa?

On Feb. 8, police arrested Thomas Stapleton at his home in the Commonwealth Hotel. A clerk in a Northside drug store, he was known to have frequented the Colony Club, and was a known thief and robber. Mrs. Lovrein identified him as the man who left with the coats. But the police never found the coats and Mrs. Lovrein did not get an especially good look at the man, so Stapleton was released a month later.

The police captain investigating the crime, William Drury, saw the case going cold. When one of his officers brought in a fresh clue, he saw an opportunity. Shortly after the murder, two girls at the old Immaculata High School on Irving Park Rd. saw a man sitting at a bus stop at the corner of Irving Park and Sheridan, holding two fur coats. The man took the Sheridan bus south to the Drake Hotel on Michigan Ave., where he egressed, leaving one of the coats on the seat. A passenger noticed and called to the man, who returned to take his coat.

Some time after Carey’s murder, one of the girls happened to mention this incident to her father, who was a police officer under Drury's command. At the time, Drury was in the middle of a bitter personal feud with a minor Outfit crook, Charles Fischetti, who was a cousin to Al Capone. Drury knew the Outfit had to have been involved in Carey’s murder somehow, and he saw the opportunity to kill two birds with one stone: solve the Carey case, and take down Fischetti.

He arrested Fischetti, and brought the two girls into the station. "I want you to identify this man as the man you saw carrying the coats," he told them. But the girls insisted Fischetti was not the man. Drury tried again, to no avail, only serving to upset one of the girls, who complained to her police officer father.

Drury got his comeuppance for framing Fischetti a few years later, in 1950, when he was gunned down in the garage behind his home, most likely by his enemies in the mob.

After Nick Circella got out of prison, the government began proceedings to deport him, and in 1955, Circella boarded a steamer for Argentina, and was never heard from in the U.S. again, although his brother August Circella, remained in Chicago as a burlesque theater operator through the 1970s.

The murder of Estelle Carey has never been solved.

Mrs. William Hale Thompson, Mayor's Wife, Robbed at Gunpoint

In the fall of 1930, William Hale "Big Bill" Thompson was serving his third term as mayor of Chicago, having defeated the incumbent "Decent" William Dever in 1927. Funded by Al Capone's syndicate and unrepentant in his connections with the city's bootleggers, Thompson was in bed with criminals, and his popularity was declining as the city's crime rates rose. Yet he never guessed just what a close encounter his wife would have with the underworld on the evening of October 6 at this spot on the corner of Barry Ave. and Sheridan Rd.

William Hale Thompson was the scion of one of Chicago's greatest families. On his mother's side, Thompson's grandfather, Stephen F. Gale, was one of the signatories to the city's original 1837 charter of incorporation. His father, Col. William H. Thompson, Sr., was a Bostonian who came to Chicago after serving at high rank in the Navy during the Civil War. Col. Thompson started a real estate business, building the "Thompson Block" on W. Madison St. The Colonel's location turned out fortuitous, as his buildings were the closest ones to downtown not burned in the Great Fire. With the higher rents he was able to charge, he made himself into one of the city's major rebuilders, and his family became the toast of society.

His oldest son, William, Jr., was a wild young man, perhaps spoiled by his family's wealth and power. Once, after his son was arrested for fighting, Col. Thompson marched directly into the mayor's office to demand William, Jr., be released, and then watched as the mayor dressed down the police chief for arresting him. Instead of heading off to Yale, as his parents demanded, young William, Jr., went adventuring in Wyoming, learning the trade of the cowboy, and then to New Mexico to start a ranch. After the passing of his father in 1891, though, he returned to Chicago to take over his father's real estate business. Nevertheless, he retained his cowboy hat as a political trademark for the rest of his life.

(Pictured: William Hale Thompson, as cowboy, on the left, with two other cowboys)

"Big Bill", as his friends began calling him, also brought back a physique in top form from years of hard work on the range, and so he became seriously involved in amateur athletics. Once, in 1893, his mother fired one of her coachmen for indolence. When the man later turned up drunk and angry at the family's summer home in Wisconsin, he shoved Thompson, who returned the aggression with his fists. With one punch from Big Bill, the man dropped dead.

Thompson excelled at swimming, yachting, and football, and quickly rose in the ranks of the Chicago Athletic Association. The football teams he managed played and defeated some of the top college teams of the day, including Northwestern and Yale. In January, 1899, however, Big Bill learned his first lesson in politics when he lost the Presidency of the Association. The Tribune reported:

Although Mr. Thompson said that good feeling prevailed between the rival factions, some of his friends said the regulars [Thompson's opponents] had employed the tactics of ward politicians to gain votes and charged a breach of good faith in one or two particulars.

Thompson took the opportunity of his defeat to run for Alderman from the Southside 2nd Ward in 1900. Nominated by the Republicans at Frieberg's Dance Hall, Thompson won the race, and represented an area that included the newly-forming "Levee," the red light district that would soon become world-famous. The Tribune endorsed Thompson's opponent, beginning a long history of antagonism between Big Bill and the Trib.

The neighboring First Ward, directly to the north, was run by those famous "Lords of the Levee," Michael "Hinky Dink" Kenna and John J. "Bathhouse" Coughlin, who became rich collecting protection from the brothels and gambling dens in their district. But the old Custom House Place levee district was under pressure and public condemnation, and there was talk of closing the old segregated vice district in favor of a new levee in the 2nd ward. Some operations, including the world-famous Everleigh Club, had already opened near Dearborn and 22nd, and others were soon to follow. Kenna and Coughlin decided they needed to broaden the boundaries of their Ward to include the new vice district in the freshman Thompson's ward.

Some accounts indicate that Kenna and Coughlin tricked Thompson into voting to shift the boundary of the 1st Ward down to 31st street; others say the vote was a back-room deal in which the 1st Ward aldermen promised to support Thompson's future mayoral aspirations. In any case, Thompson stepped down from his Aldermanic post after one term, and ran for county commissioner, serving in that capacity for two years before running, unsuccessfully, as an independent candidate for mayor in 1905.

At about the same time he left his Aldermanic office, he fell in love with Mary "Maysie" Walker, a secretary in his father's bookkeeper's office. Thompson's mother disapproved of the marriage, so the couple eloped to Michigan to marry. Settling down with his bride, Thompson continued running his real estate business, dabbling in Republican politics, taking control of the Columbia Yacht Club, and managing amateur football teams for the next decade.

(Pictured: Mary Walker "Maysie" Thompson)

Finally, in 1915, he ran again for mayor, this time on the Republican ticket. A newspaper account at the time described him:

Even in his forties, with some of the signs of middle age in his face and figure, he has the great depth of chest and the breadth of shoulder which mark the athlete. There is nothing about him which suggests the student.

Running against Democrat Robert Sweitzer, the campaign was dirty from the outset. Both sides accused the other of close ties to disgraced Illinois Sen. William Lorimer. As it was the first Chicago election in which women were allowed to vote, Thompson never missed an opportunity to display his rugged good looks and handsome frame. He also promised to enforce the Sunday saloon closing laws, a policy supported by most women. On the evening of his victory in the 1915 campaign, Mrs. Thompson told a reporter, "It is a women's victory...Billy stands for everything that is good for the city, and I will stand by him and second him in everything that he will do for us."

Upon election, Thompson immediately began floating his name for the 1918 Illinois Senatorial contest, and as a potential candidate for U.S. President in 1920. After all, if he was able to win solidly Democratic Chicago by 148,000 votes, just think what he could do for the Republican party on the national level.

But Thompson's first term was a disaster. At the onset of WWI, Thompson was an avowed peacenik, opposing America's involvement in Europe, and courting the vote of Chicago's large German population. Detractors began referring to him as "Kaiser" Bill Thompson, and he was consistently booed and hissed in Peoria and other downstate locations during his 1918 Senatorial campaign. The Tribune chimed in,

Having opposed the war and the draft and having objected to the sending of drafted men to Europe, it is not likely that Thompson will be very sincere in his promise to do all he can to help prosecute the war "until the United States can obtain peace with honor."

When it was revealed that the Germans were using Thompson's speeches in propaganda used against American troops, he lost his Senatorial campaign. Though he managed to maintain the mayor's office in the 1919 re-election, his popularity continued to slide as several major graft scandals arose, including his failure to keep some parts of the old Levee district, which had been shut down in the early part of the 1910s, from reopening (perhaps as a payback to Kenna and Coughlin?). His slow response to the deadly race riots of 1919 didn't help either. By 1923, Big Bill realized he couldn't win a third term, and he "retired" from politics.

During the 1920s, Thompson maintained a high profile, contributing to political campaigns, becoming involved in civic affairs, and continuing his passion for yachting. He was a major investor in the "Fish Fans Club," a sort-of booze cruise in Belmont Harbor, which when the police raided, was found to be full of illegal liquor. However, to the majority of Chicagoans who opposed Prohibition, Thompson, unlike his mayoral successor, "Decent" William Dever, was a man of the people.

Thus, in 1927, Thompson ran against Dever in one of the nastiest political campaigns in the city's history. Implicitly promising to "take off the lid" on alcohol consumption in Chicago, Thompson kicked off his campaign at the Sherman House, where he had recently become close friends with Al Capone. In one memorable speech, Thompson referred to Dever as "the biggest liar and the biggest crook who ever broke an oath of office." For his part, Dever returned the compliment: "I don't know what ails the man. I don't like to say he's crazy. But there is mental trouble of some sort there, I am sure....There isn't anybody home with that man. He simply can't conceive serious or consecutive thought."

By cobbling together the votes of Southside African-Americans, a wide range of recent immigrants, and other Chicagoans who just wanted a beer, Thompson won in 1927. It also didn't hurt that Thompson's campaign coffers were filled with Capone money, a fact that was evident to anyone who cared to look carefully.

(Pictured: Thompson as mayor, with trademark cowboy hat)

On the night of his victory, Mrs. Thompson was triumphant. "Anytime anybody wants to try to run against that boy, he's in for a smashing licking....He showed 'em. You bet he showed 'em; he showed 'em!"

By 1930, however, the Thompsons' marriage (like Big Bill's political career) was on the rocks (they separated a few years later), so it's no surprise that on the night of October 6, Mrs. Thompson went out to a show downtown together with her sister. At around 11:00, Mrs. Thompson's driver, a Chicago police officer, picked the two up outside the theater, and drove first to Lincoln Park to drop off the Mayor's sister-in-law at her apartment. Just before midnight, Mrs. Thompson's driver pulled up to the Barry St. entrance to their apartment building, at 3100 N. Sheridan (entrance pictured above, building pictured at bottom).

As her driver exited the car to help Mrs. Thompson with her door, three men stepped out of a Nash automobile parked in front and jumped the officer, forcing him back into the vehicle, where one of the robbers held a pistol to his head, disarmed him, and ripped the police star off his vest. The other two forced the city's first lady into the vestibule of the building, pressed guns against her forehead and side, and demanded her jewels. Liberating her of a 6.5-carat blue diamond ring, a 40-diamond bracelet, and a diamond brooch set, the men took off in their car.

Mrs. Thompson fainted and fell to the ground. At just that moment, two fellow residents of the 3100 building, Barney and Mrs. Balaban happened on the scene, and carried Mrs. Thompson up to her apartment, where she spent several days ill as a nervous wreck (Balaban was a Chicago theater magnate and would soon become president of Paramount Pictures in Hollywood).

The mayor arrived home at 2:00 a.m., and the next morning called the chief of police into his office. "Remember what I say. I want action, and I want action immediately," he demanded. Thompson had fired a previous police chiefs during his first term for political gain, so the implications were obvious. With no leads except Mrs. Thompson's description of one of the gunmen as "handsome, a good-looking youth," the police picked up a criminal they wanted out of the way, in the hope that a jury would convict him based on his unsavory police record alone.

That man was Sam Battaglia (also known as "Teets"), leader of the "42" gang. The 42s were a group of toughs from the impoverished Bloody Maxwell neighborhood who specialized in beatings and auto thefts, lending their services out to bootleggers (especially the Gennas) and union racketeers throughout the 1920s. Battaglia and a fellow 42, William Carr, were arrested for the robbery and put on trial, but witnesses were unable to identify Carr on the stand, and he was dismissed from court. Despite being identified by Mrs. Thompson and others, Battaglia was acquitted due to insufficient evidence, and the missing jewels were never recovered.

(Pictured: Sam "Teets" Battaglia)

Mayor Thompson's political rivals were quick to make a point of his wife's victimization: "The mayor, two months ago, should have supported my resolution for an investigation of the police department with the same vigor with which he fought King George," said one Alderman.

The crack about Big Bill fighting King George refers to Thompson's 1927 campaign, in which he famously courted the votes of Southside Irish with ridiculous arguments that King George V (then King of England) was the greatest contemporaneous threat to the United States. Thompson promised that if the King visited Chicago, the mayor personally would "bust him on the snoot."

With the city's crime wave out of control, Mayor Thompson faced an uphill battle in the 1931 mayoral election, in which he faced off with Democratic challenger Anton Cermak, and if the mayor couldn't keep his own wife safe, what were other Chicagoans supposed to expect? Thompson's poorly-run campaign, in which he gave up on his winning strategy of courting immigrant votes by belittling Cermak, making fun of his name, and never failing to point out his foreign birth, didn't help his cause either. In an early sign of the Democratic wave sweeping the country, "Big Bill" lost the '31 election by the widest margin in the history of the city up to that time. Though he ran as a reformer, Cermak turned out to be only marginally less corrupt that Thompson.

After running unsuccessfully for Illinois governor in 1936, and for Chicago mayor again in 1939, William Hale Thompson died in March, 1944. When his family checked the ex-mayor's three safe deposit boxes, they were shocked to find $1,840,000 in unreported cash. Thompson's friends argued that it was likely the fruits of the real estate business Thompson had run while not in office. But safe deposit boxes pay notoriously low interest rates, so the presence of the cash suggests an illegal source. Were these payoffs from Capone and other mobsters? Or was Thompson able to reap large real estate returns while in office, based on inside information about city public works plans? We'll never really know, but after the IRS took its share, Mrs. Thompson lived on the rest until her passing in 1958.

One of Sam Battaglia's fellow 42s, Sam "Mooney" Giancana, later became a major figure in the Chicago Outfit, organizing its lottery gambling operations in the 1940s. He brought Battaglia and several other 42s into the hierarchy of the gang, making them rich beyond the wildest dreams they ever had on the tough Westside streets where they grew up. Battaglia lived until 1972.

The Barry Apartments, where the Thompsons lived during the 1920s, still stands, and is still an apartment building. Perhaps not quite as tony as it was when the Mayor and the future president of Paramount Pictures lived there, it is still a desirable location in the Lakeview neighborhood, near the beach.

Manhattan Brewing Company

The Manhattan Brewing Company was incorporated in 1892. Producing suds at 3901 S. Emerald, in Chicago, it always seemed to have an locational identity crisis.

For the first 27 years of its existence, it was a large, but otherwise ordinary brewery (one exception was an accidental explosion in 1908 that killed two workers, and could be heard throughout the South side).

In 1919, at the start of national Prohibition, Joseph Stenson, a top Chicago brewer, along with South side gang leader Johnny Torrio, bought the brewery, changing its name to Fort Dearborn Products -- although it continued to make beer. After Torrio's departure from Chicago, the brewery fell into the hands of Al Capone, and it became one of the largest manufacturers of alcoholic beverages during Prohibition.

In the early 1930s, with Capone in prison and Prohibition ended, the brewery came to be held largely by Capone's chief accountant, Louie Greenberg. Greenberg changed the name back to Manhattan, and later began producing a sister brand, Canadian Ace. That the brewery remained in the hands of organized crime is evident from the continued attempted bombings of the factory throughout the 1930s. In the 1940s, Greenberg attempted to open a sister brewery in New York with business partners including prizefighters Joe Lewis and "Sugar" Ray Robinson, but was turned down by state authorities due to his connections with the Outfit in Chicago.

In the 1940s, the Federal Trade Commission successfully sued the brewery on false advertising charges, since Canadian Ace was produced on the South side of Chicago, not in Canada (or in Manhattan!). Both Manhattan Beer and Canadian Ace were highly successful brands in the 1940s, 50s and 60s.

After Louie Greenberg was assassinated in 1955, the brewery continued to operate, but faced with increasing competition and a lack of gang muscle, it finally shuttered in 1968. The factory was demolished in the mid-1970s. The lot is empty and overgrown with brush today.

For more about the Manhattan Brewing Company, including historic photos, see this fansite.