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.