On September 16, 1931, three men walked into an apartment building on Collingwood Avenue in Detroit and never walked out. The killings, carried out by members of the feared Purple Gang, became one of the most notorious slayings of the Prohibition era and marked the beginning of the gang’s collapse. The victims—James Paul, Joe Leibowitz, and Isadore Sutker—were associates of the gang who had been summoned to apartment 211 for what they believed was a routine meeting. Instead, they were shot dead in a matter of seconds.
Police found the bodies with their hats still on, a detail indicating the men never had time to react to what was happening. The building at 1211 Collingwood Avenue still stands today, but the events of that day helped bring down an organization that had once controlled the illegal alcohol trade along the Detroit River and commanded respect—and payment—from mob figures across the country, including Al Capone. The Purple Gang emerged from the Jewish immigrant neighborhoods of Detroit’s lower east side in the early 1900s. Its core leadership consisted of the four Bernstein brothers—Abe, Ray, Izzy, and Joe—along with associates such as Harry Keywell, Irving Milberg, and Harry Fleisher.
The group was reportedly named by a local shopkeeper who described its members as “purple”—rotten and off-color, like bad meat. When Prohibition took effect in 1920, the gang seized an extraordinary opportunity. Detroit sat across a narrow river from Canada, where whiskey production continued uninterrupted. The Purple Gang controlled the smuggling routes, the storage warehouses, and the distribution networks, charging anyone who wanted to operate in the city.
Their reputation for violence was well documented; they were linked to more than 500 murders in Detroit during the 1920s. Al Capone, the most powerful gangster in Chicago, did not try to challenge the Purple Gang’s dominance. Instead, he negotiated with them and paid for access to their Canadian whiskey connections. Beyond bootlegging, the gang moved into other rackets.
From roughly 1925 to 1928, they muscled into Detroit’s dry cleaning and laundry trade through an extortion scheme disguised as a protective association. Business owners who refused to pay faced acid attacks, bombings, and beatings. Several establishments were burned to the ground and at least three men connected to the dispute were killed. By 1931, the Purple Gang was at the height of its power, but internal tensions were building.
The three men killed at Collingwood Manor were part of a semi-independent faction known as the Third Avenue Navy. They had worked alongside the Bernsteins but were not fully under their control, and by 1931 the Bernsteins had decided they were a problem. The exact reasons vary in historical accounts. Some sources say the victims had been encroaching on Purple Gang territory.
Others point to personal disputes or concerns that the men had been talking too freely to the wrong people. Whatever the precise cause, Ray Bernstein—the tactical mind of the gang—organized a solution designed to look like a peaceful reconciliation. An apartment was rented at Collingwood Manor through a front man named James Rugase, whose only role was to sign the lease. The meeting was arranged, and when Paul, Leibowitz, and Sutker arrived, they were met by Ray Bernstein, Harry Keywell, Irving Milberg, and at least one other gunman.
The shooting was over in less than a minute. The case might have gone unsolved, as others had, if not for a witness. James Vivian, a resident of the building, heard the shots, saw the faces, and talked to police. Within a day, Bernstein, Keywell, and Milberg were arrested.
The trial became one of the most closely watched criminal proceedings in Michigan history. The key witness was Saul Levine, a Purple Gang associate who had been present during the murders but was not one of the shooters. Taken into protective custody, Levine chose to testify against his former partners. He described the planning, the setup, and the moment the shooting began.
The defense attacked Levine’s credibility, labeling him a murderer whose word should not be trusted. The jury deliberated for less than two days before convicting all three men of first-degree murder. Bernstein and Keywell received life sentences. Milberg was also sentenced to life and died in prison in 1938.
The verdict sent a message far beyond Detroit. It proved that a jury could convict a Purple Gang member of murder, something many believed impossible given the gang’s record of witness intimidation and corruption. Newspapers across the country covered the case, and criminal organizations from Chicago to New Orleans understood that their aura of immunity was not absolute. The conviction also destabilized the gang from within.
The remaining leadership became paranoid, seeing informants everywhere. Internal killings increased as Purple Gang members turned on one another, convinced that someone was cooperating with authorities. At the same time, the gang’s primary business was disappearing. Prohibition was repealed in December 1933, making the whiskey trade legal.
The Purple Gang tried to pivot to gambling and loan sharking, but without the Prohibition money and without the imprisoned Bernstein brothers leading the operation, the organization fragmented. By the mid-1930s, the Purple Gang had essentially ceased to exist as a coherent force. Members joined other outfits, were absorbed by Detroit’s Italian mob, or drifted into civilian life. Abe Bernstein, the eldest brother, survived the collapse.
He avoided conviction, outlived most of his contemporaries, and died in 1968 at an old age. Ray Bernstein served nearly 20 years in prison, was paroled in 1964, and died a year later. He never publicly discussed the Collingwood murders. The significance of the case extends beyond the story of one gang.
The trial is seen as an early turning point in American law enforcement’s ability to hold organized crime accountable. It showed that prosecutors could win convictions in high-profile murder cases involving mob figures, that juries could return guilty verdicts, and that witnesses could survive long enough to testify. That precedent carried forward through later prosecutions, from the Kefauver hearings of the 1950s to the RICO cases of the 1970s and 1980s. The Collingwood Manor building still stands at 1211 Collingwood Avenue.
It has been renovated many times over the decades. Apartment 211 still exists inside whatever the current floor plan looks like. Three men entered that building on September 16, 1931, expecting a conversation. They were killed before they understood what was happening.
The murders were meant to consolidate the Purple Gang’s power and eliminate problems. Instead, they began the process that destroyed the gang, proving that the violence meant to protect the organization was the very thing that brought it down.