The Purple Gang Massacre That Shocked America HT

 

September 16, 1931, 3:28 p.m. Apartment 211, 1740 Collingwood Avenue, Detroit. Three men walked into what they thought was a peace conference. They walked in unarmed, trusting. 15 seconds later, all three were dead. Blood pulled under a couch. Cigars still clenched in dead hands. Bullet holes peppered the walls.

This wasn’t just another gangland hit. This was the murder that ended an empire. The men who died that day were smalltime hustlers who’d made one fatal mistake. They’d crossed the Purple Gang. And the Purple Gang, Detroit’s most violent criminal organization, didn’t forgive. They didn’t negotiate. They eliminated.

 But here’s what nobody saw coming. The massacre that was supposed to prove the Purple Gang’s invincibility became the moment that destroyed them forever. Three murders, three life sentences, and the complete collapse of America’s most feared Jewish mob. This is the story of how ambition, betrayal, and three and a half minutes of gunfire brought down a criminal empire that had survived everything law enforcement could throw at it.

 This is the story of the Collingwood Manor massacre, the day Detroit’s underworld changed forever. But to understand why those three men had to die, you need to understand what the Purple Gang was and what they were capable of. Detroit, 1920. The Volstead Act had just made alcohol illegal across America.

 And Detroit had just become the most valuable piece of real estate in organized crime. You had Canada directly across the Detroit River, less than a mile of water in some places. 45 legal distilleries operating in Ontario and a city of over 1 million thirsty auto workers with money in their pockets. It was a smuggler’s paradise. By 1929, illegal liquor was Detroit’s second biggest industry at $215 million a year.

Only automobiles brought in more money. 50,000 people worked in the illegal alcohol trade. 25,000 speak easys operated openly. And one gang controlled it all. The Purple Gang. They weren’t the biggest gang. They weren’t the most sophisticated, but they were absolutely the most violent. Detroit police credited them with over 500 homicides.

500. They hijacked shipments. They murdered competitors. They bombed businesses. They corrupted unions. And they did it all with a level of brutality that terrified even other criminals. The gang was led by four brothers, Abe, Joe, Raymond, and Izzy Bernstein, sons of Russian Jewish immigrants who’d come to Detroit’s east side ghetto searching for a better life.

What they found was poverty. What their sons created was a criminal empire. Abe was the oldest, born around 1892. He was the strategist, the businessman, the one who negotiated with Meer Lansky and owned casinos in Miami. the one who maintained relationships with Al Capone in Chicago.

 Abe understood that violence was a tool, not a solution. He built alliances. He thought long term. His brother Raymond was different. Ray Bernstein was the enforcer, slim, blue-eyed, with a permanent scowl carved into his face. Ray believed problems were solved with bullets. He was the one who ordered hits, the one who pulled triggers, the one who terrified people just by walking into a room.

 The purple gang started small. Shoplifting, extortion, shaking down merchants in the Jewish quarter, but prohibition transformed them. By the mid 1920s, they’d become sophisticated. They hijacked liquor from rum runners along the Detroit River. They partnered with a group called the Little Jewish Navy, who smuggled Canadian whiskey across frozen Lake St. Clair in speedboats.

 They supplied Al Capone’s entire operation in Chicago. The whole Midwest ran on purple gang liquor, and they protected their territory with extreme prejudice. March 1927, the Mila Flores Apartments. Three gunmen from the rival Oakland Sugar House gang showed up for a peace meeting. A Baxler and Eddie Fletcher, two purple gang members, were hosting.

 The three men walked in. They never walked out. Machine gun fire tore through the apartment. When it stopped, police counted 110 bullet holes. It was the first time a Thompson submachine gun had been used in a Detroit murder. The Purple Gang had just introduced automatic weapons to the city’s underworld. Nobody was ever convicted.

Then came 1928. The Cleaners and Dyers War. The Purple Gang hired themselves out to enforce union control in Detroit’s laundry industry, bombing non-UN shops. Beating workers who wouldn’t join, extorting protection money from business owners. Nine purple gang members were arrested and charged with conspiracy to extort.

The trial was a joke. Someone broke into the union offices before trial and stole every document that could prove the case. The jury acquitted everyone. This was the Purple Gang’s power. They operated in plain sight. They murdered witnesses. They corrupted courts. They terrorized an entire city. Law enforcement was helpless.

 But by 1931, cracks were appearing. The problem wasn’t the police. It was internal. The Purple Gang’s brutality had created too many enemies. And some of those enemies used to be allies. and her three men who thought they were smart enough to play both sides. Herman Paul, 31 years old, everyone called him Haimey.

 Joseph Leowitz, also 31, known as [ __ ] Joe, a nickname common at the time for anyone with dark features. And Isidor Sutker, 28, called Izzy the rat. All three were from Chicago. All three had been run out of town by Al Capone after they tried to shake down speak easy operators who were under Capone’s protection.

 Capone gave them a choice. Leave Chicago willingly or leave in a box. They chose Detroit. Big mistake. The three men joined up with a smaller faction of bootleggers called the little Jewish Navy. They were supposed to be muscle protection for liquor shipments coming across from Canada. But Haimey, Joe, and Izzy weren’t interested in being anyone’s hired guns. They wanted to be bosses.

They started their own bookmaking operation. They got into the wholesale liquor business. They called themselves the Third Avenue Terrors, named after the railroad yards between Third and Fourth Avenues, where they landed their Canadian whiskey. And they broke every rule of Detroit’s underworld. They hijacked from friends and enemies.

 They double crossed business partners. They refused to stay in their lane. They stepped on the Purple Gang’s territory. Inspector Frank Freillley, who ran the precinct where they operated, called them out personally. He evicted them from the Orlando Hotel after receiving complaints they were using rooms as an office.

 He told them to get out of his precinct. They ignored him. Here’s where things got fatal. Spring 1931, the Third Avenue Terror’s bookmaking operation was booming. They’d taken in a partner named Solomon Lavine. Everyone called him Sulli, 30 years old, local hood. Longtime acquaintance of the Bernstein brothers from the old neighborhood, the perfect bridge between the two groups.

 Then the Eastside Mafia hit a big parlay on their book. A massive bet worth hundreds of thousands of dollars. money the Third Avenue terrors didn’t have. They were broke. Izzy Sutker had just been evicted from his apartment for non-payment of rent. They’d lost their cars because they couldn’t keep up payments. And now they owed the Italian mob a fortune they couldn’t pay.

 Desperate, they went to the Purple Gang, bought 50 gallons of whiskey on credit. Then they diluted it with water. Sold it below market price for quick cash. Paid off the Italians. The Eastside Mafia came back with another fixed horse race. Another huge winning bet. The terrors were in deeper trouble. They went back to the Purple Gang. Another 50 gallons on credit.

Another delution. Another quick sale. Ray Bernstein found out. You have to understand what this meant. The Third Avenue Terrors hadn’t just stolen from the Purple Gang. They’d shown disrespect. They’d demonstrated that they thought the Purples were suckers. In the world of organized crime, that’s a death sentence.

 But September 1931 was boom time for bootleggers. The American Legion National Convention was coming to Detroit. Every speak easy, cabaret, and blind pig in the city had placed massive orders for booze. The Third Avenue Terrors thought they could make everything right if the Purple Gang would just give them time until after the convention.

 Ray Bernstein sent word through Sally Lavine a meeting to work things out. The terrors would handle horse bedding and alcohol sales. Once they straightened out their debt, everything would be forgiven. Haimey Paul, Joe Leowitz, and Izzy Sutker relaxed. They thought they’d negotiated their way out. They thought they were back on track to Easy Street.

 They were wrong. September 16, 1931. Early afternoon, Sally Lavine was working at the bookie joint when a purple gang member called. He gave him an address. 1740 Collingwood Avenue. Apartment 211. Be there at 300 p.m. Lavine wrote it down on a pink bedding slip. That afternoon, the four men left the book around 2:45. They were unarmed.

You don’t bring guns to a peace conference. They arrived right on schedule. Quiet residential neighborhood on Detroit’s west side. Nice apartment building. Nothing suspicious. Ray Bernstein met them at the door. Inside apartment 211, a photograph was playing. As the men entered, someone turned it off mid song.

 Left the needle scratching in the groove. Three other purple gang members were waiting. Irving Milberg, 28 years old, receding hairline that made him look older. Criminal record spanning a decade. Armed robbery, assault, disturbing the peace. Known as a crackshot with a pistol. Harry Keywell, 20 years old, babyface, innocent looking.

 His rap sheet included illegal firearms, possession, and assault with intent to do great bodily harm. He’d been accused, but never convicted, of participating in the St. Valentine’s Day massacre in Chicago, a killer who wasn’t old enough to vote. and Harry Fleer, 29 years old, slightly built, wanted by federal authorities.

 His record included assault with intent to kill, armed robbery, kidnapping, receiving stolen property. He was supposed to be on the run. His presence at the apartment was a surprise. Paul, Si Lavine, and Joe Leowit sat down on a couch together. Izzy Sutker sat on the arm. They chatted. Friendly conversation. Everything seemed fine.

 Then Flecher looked at Ray Bernstein, asked where the accountant was, the guy with the books, who was supposed to go over their debt. Bernstein said something about going to look for him. He left the apartment, went down to the street where a 1930 Chrysler was waiting, started the engine, raced it loud enough to wake the neighborhood, laid on the horn.

 That was the signal. Harry Fleer pulled out his 38 caliber revolver, aimed at Joe Leowitz’s head, fired. The bullet passed so close to Si Lavine’s nose, he felt the heat. At the same instant, Milberg and Keywell opened fire on Sutgar and Paul. The three men scrambled, tried to run, tried to find cover, tried to escape. Haimey Paul made it three feet.

He slumped against the couch in the living room, eight bullets in his back and head, a cigar still clenched in his hand. Joe Leowitz made it to the short corridor leading to the bedroom. He died there. Battered cigar stubs still in his teeth. Izzy Suter made it into the bedroom.

 Two bullet holes less than an inch apart right in his forehead. A stogy in his hand. 15 seconds. 21 shots. Three dead men. Izzy had 11 cents in his pocket. Haimey had $2. Joe died with $92 on him. That’s what their ambition was worth. Flecher turned to Si Lavine. The only living witness asked if he was okay.

 Lavine nodded, speechless, waiting for his own execution. It never came. The three killers huddled, then told Lavine to follow them. They ran to the kitchen where they dropped their revolvers into a bucket of green paint. The paint destroyed any fingerprints. They’d also filed off the serial numbers. No evidence. Lavine, Milberg, and Keywell ran down to the waiting Chrysler where Ray Bernstein sat at the wheel. Moments later, Fleer appeared.

 He said Joe Leawitz was still breathing a little. He’d put a few more bullets in him to finish the job. A young mother trying to put her baby down for a nap, heard the shots, rushed into the hall, saw Fleer taking the stairs two at a time toward the alley. The Chrysler tore out of the alley, nearly ran over a small boy playing in the street, burned the tires on the alley pavement.

 The apartment caretaker, Harry Macdonald, watched them go. He later told reporters they moved quickly, but didn’t seem excited. Professional. The killers drove like hell for a few blocks. Then they split up. Ray Bernstein shook hands with Sally Lavine. Told him, “I’m your pal.” Sally gave him $300 or $400.

 told him to go back to the book. He’d pick him up later. What Lavine didn’t know was that Bernstein planned to kill him that night and frame him for the murders. But the police moved faster than Ray Bernstein anticipated. Within an hour, Si Lavine was in custody. He tried to lie, told police he and the three dead men had been kidnapped on their way to meet with bootleger Harry Klene.

 Said he didn’t see who did it, but he couldn’t keep his story straight. told it differently every time. Detectives knew he was lying. Wayne County prosecutor Harry Toy issued a statement to the press. We want the gunman dead or alive. There will be no deals. We’ll go and get them. The city erupted.

 For years, the Purple Gang had operated with impunity. Witnesses too terrified to testify. Judges too corrupt to convict. Police too outmatched to investigate. But this time was different. This was a massacre in a residential neighborhood in broad daylight. Three men executed. A city demanded justice. The police drag net up immediately.

 Scores of telephone calls poured in with tips. The underworld itself was turning on the purple gang. Rivals saw an opportunity to eliminate their competition. The information flooded in. 48 hours later, police got an anonymous call. Two of the men you want for the Collingwood murder are at 2,649 Calvert.

 They’ll be out of town within the hour. Heavily armed officers surrounded the apartment. It belonged to Charlie Hourback known as the professor. Listed occupation jewelry salesman. Real occupation purple gang consultant. Inside were Ray Bernstein and Harry Keywell. Both arrested in their pajamas. Also present were Hourbach, his wife, and an 18-year-old cabaret entertainer named Elsie Carol, smartly dressed, flipcracking blonde, reportedly the girlfriend of Izzy Bernstein.

 The women were carrying over $9,000 in cash. Police found tear gas and guns throughout the house. Ray Bernstein’s swagger was gone. Detectives said he looked nervous. The next day, Irving Milberg joined them. Police raided his flat on West Chicago Boulevard. His wife called the house while they were there. The call was traced to purple gang member Eddie Fletcher’s apartment three blocks away. Officers burst in.

 Found Abe Axler, Irving Milberg, and Eddie Fletcher playing cards. Packed suitcase in Axel’s car. Five pistols and a rifle ready for action. Milberg tried to escape through a window, punched out the screen. They caught him anyway. Three killers in custody. Si Lavine willing to testify.

 For the first time, prosecutors had everything they needed to break the purple gang. The preliminary examination began September 30th. Si Lavine appeared terrified, but he pointed at Ray Bernstein, Harry Keywell, and Irving Milberg. identified them as the killers. Said Harry Fleer also participated, but Flecher had disappeared.

 During his testimony, Lavine never once looked at the accused men. He focused only on the prosecutor. The three defendants stared at Lavine the entire time, glaring, trying to intimidate him. It didn’t work. October 2nd, the men were arraigned before Judge Donald Vanzyle. Defense attorneys filed a motion to dismiss based on Lavine’s testimony being unreliable. The motion was denied.

The judge ordered the men held without bond. November 2nd, 1931, the trial began. Sali Lavine took the stand. Eight detectives guarded him constantly. 10 more stood guard during the trial. Four detectives stood at point while he testified. He feared assassination in the courtroom. He told the story, the meeting, the photograph, Ray Bernstein leaving, the signal, the gunfire, the escape, every detail.

Witness after witness corroborated his account, neighbors who saw the men flee the building, people who heard the shots, the young mother who saw Fleer running down the stairs, the apartment caretaker who watched the Chrysler burn rubber out of the alley. The defense tried everything.

 Claimed Lavine was the real killer. Suggested the victims were killed by the Italian mob. Attacked Lavine’s credibility. None of it worked. The jury deliberated for 1 hour and 37 minutes. They returned with a verdict. Guilty. Firstdee murder. All three defendants. Ray Bernstein, Harry Keywell, Irving Milberg. Sentenced to life in prison without possibility of parole.

 Sent to Marquette Prison in Michigan’s Upper Peninsula. Chief of Detectives James McCarti made a statement to the press. This conviction is the greatest accomplishment in years. Not only does it break the back of the Purple Gang, but it serves notice on other mobs that murder doesn’t go anymore in Detroit. He was right. The Collingwood Manor massacre accomplished what years of police work couldn’t.

 It took down the Purple Gang’s leadership. Ray Bernstein, one of the four founding brothers, was gone forever. Harry Keywell and Irving Milberg, two of the gang’s most prolific killers, were off the streets. And the myth of the Purple Gang’s invincibility, was shattered. Si Lavine had done what no witness had ever done before.

 He testified against the Purple Gang and lived. That changed everything. Other witnesses came forward. Other cases were reopened. The wall of silence crumbled. But there’s a postcript to this story. 9 months after the trial, Harry Fleer did the unthinkable. June 9th, 1932, he walked into the prosecutor’s office with his attorneys and turned himself in.

 He’d been a suspect in multiple major crimes while on the run, including the Lindberg baby kidnapping. Now he was ready to face charges. There was just one problem. Sully Lavine had disappeared. The prosecution couldn’t find their star witness. Without Lavine’s testimony, they had no case. By July 25th, prosecutor Harry Toy was forced to admit defeat.

 The case against Harry Fleer was dismissed. He walked free. The judgment against Bernstein, Keywell, and Milberg stood, but Flecher had beaten the system. What happened to the others? Si Lavine vanished. Some say the purple gang got to him. Some say he was relocated by authorities. Some say he simply ran as far and as fast as he could. Nobody knows for certain.

 He was never seen again. Abe Bernstein, the brains of the operation, was never charged with the Collingwood massacre. He continued operating in Detroit, but his power was broken. The other families moved in. the Italians, the Irish. The territories that once belonged to the purples were carved up. Abe died in 1968, March 7th. He was 76.

 He’d outlived his empire by three decades. Ray Bernstein suffered a stroke in Marquette prison. He served his entire life sentence, died behind bars. Harry Keywell served 64 years in prison. He was finally parrolled in 1995 at age 84. Two years later, he died in Palm Beach, Florida. August 30th, 1997.

 He’d spent most of his life in a cell for 3 and 1/2 minutes of violence when he was 20 years old. Irving Milberg didn’t make it that long. He died in prison in 1938, 7 years after the massacre. He was 35. The Purple Gang itself collapsed within 2 years of the Collingwood Manor massacre. internal rivalries, law enforcement pressure, the rise of the Italian mafia.

 By 1933, the gang that had terrorized Detroit for a decade no longer existed. So, what does this story tell us about organized crime? The Purple Gang’s mistake wasn’t the massacre itself. It was thinking they were untouchable. For years, they’d operated in plain sight. murdered witnesses, corrupted officials, terrorized a city, and they got away with it because nobody would testify.

Nobody would break the code of silence. But the Collingwood Manor massacre was different. It was too brazen, too public, too brutal, and it created a witness who had nothing left to lose. Sai Lavine knew the Purple Gang planned to kill him. Testifying was his only chance at survival, and that testimony brought down an empire.

 There’s a lesson here. Violence is a tool that criminal organizations use to maintain power. But excessive violence becomes a liability. It creates too many enemies. It draws too much attention. It makes people desperate enough to break the silence. The Purple Gang thought the Cullingwood Manor massacre would cement their control over Detroit.

 Instead, it destroyed them. three murders, three life sentences, and the end of America’s most violent Jewish mob. On September 16, 1931, three small-time hustlers walked into apartment 211 at 1740 Collingwood Avenue. They thought they were going to negotiate their way out of debt. Instead, they became the catalyst for the destruction of the gang that killed them.

 Sometimes in the underworld, winning the battle means losing the war. The Purple Gang won that day in apartment 211 and lost everything that mattered. If you want to hear more stories about the mob’s rise and fall, hit that subscribe button. We drop a new documentary every week, diving deep into the underworld’s most shocking moments, and drop a comment.

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