The beginning of the end for the Purple Gang came as Detroit prepared for an upcoming national convention of the American Legion. Stressed bootleggers struggled to keep up with demand for booze and tempers wore thin as rival gangs hijacked and re-hijacked shipments of alcohol. A bookmaking operation that couldn’t cover its bets, a crackdown by federal agents and a long-time feud between the Purple Gang and some out-of-town upstarts who wouldn’t follow orders set the stage for a showdown that is unmatched in the history of Detroit for its ferocity.

In a killing that would the shock city and result in banner headlines for weeks in the three Detroit newspapers, some hard-line Purple gangsters settled an old score but set themselves up for a fall that would signal the end of the gang’s influence in Detroit rackets.

Hymie Paul, Joe "Nigger Joe" Lebowitz, both 31, and 28-year-old Joe "Izzy" Sutker were brought to Detroit by Leiter and Schorr’s Oakland Sugar House Gang as "rod men" to protect the mobs lucrative alcohol supply racket.

But the three men weren’t interested in being someone else’s gunsels and they soon decided to branch out on their own. Paul, Lebowitz (a.k.a. Liebold), and Sutker (a.k.a. Sutton) chose the racetrack handbook racket and the wholesale liquor business.

The trio did their job well, associating with the Third Avenue Navy, a gang which earned its moniker because it landed its cargoes of Canadian whiskey in the railroad yards between Detroit’s Third and Fourth Avenues. But the men disregarded the strict code of Detroit’s underworld. They hijacked from friends and enemies and double-crossed business partners. They refused to stay within their own boundaries and stepped on the toes of neighboring gangs.

They were known as "the Terrors of the Third street district," according to police Inspector Frank Fraley, who had sparred with the gang. Fraley evicted the boys from the Orlando Hotel after he received complaints that the gang was using rooms there as an office.

"I told them we did not want them in our precinct and to get out," he told the Detroit Times.

In the spring of 1931, the trio’s bookmaking operation was gearing up. They had taken in a local hood, Solomon "Solly" Levine and everything was looking good for the boys until the East Side Mafia, which had been giving their book some serious play hit a big parlay worth a couple hundred grand.

It was money the gang didn’t have. In fact, they were broke. Sutker, his wife Doris and their 5-year-old daughter had recently been evicted from their apartment for non-payment of rent and the boys had lost their "large, high-powered cars" because they were unable to keep up the payments.

The trio, afraid of reprisals if they welshed on the bet, bought some booze from the Purples on credit, diluted it and undersold the market for a quick profit.

"The east side gang came back again with another ‘boat race," a fixed horse race, taking the handbook for even more money," wrote Joe Wolff, a Detroit News writer, in 1971. "Again a deal was made with the Purple Gang to get 50 gallons on credit. Again they diluted the stock and undersold the market price.

"They had pushed their luck. Their activities spelled death; it was just a matter of time and which gang would move to stop them first."

Autumn 1931 was a busy time for bootleggers in Detroit. The American Legion convention was coming to town and huge orders for illicit booze had been placed by the various blind pigs, cabarets and speakeasies around the city.

The three partners knew that they were in deep and felt that they could make it up when the Legionnaires came to town.

"They owed (Ray) Bernstein some money for whiskey and they wanted to get him to hold off until after the legion convention," Solly Levine told the Detroit News the day after the fates caught up with the trio. Bernstein said he would get in touch and that something would be worked out.

"We’ve got everything straightened out and we’re going to let you boys handle the horse bets and alcohol when you straighten out that bill," Bernstein, slim, a blue-eyed, man with a perpetual scowl, told Levine.

Levine was the perfect go-between for the rivals. He was a partner in the bookmaking operation and had a long-time acquaintance with many of the Purple Gang, growing up in the same neighborhood as the Bernstein brothers.

A peace conference sounded good to the three partners and they relaxed a bit, thinking that they were back on the way to Easy Street.

That night, Izzy Sutker sent a couple of his henchmen to Port Huron to pick up his 18-year-old girlfriend, Virginia White. The two of them spent the night at a cabaret near the bookie joint drinking and listening to a band.

Hymie Paul went to bed early, secure in the fact that a meeting would be held to set things right.

Lebowitz was also feeling cocky and spent a rousing night on the town, waking up the next morning with a hangover so bad he didn’t bother to shave.

On September 16, Levine was working at the bookie joint when one of the Purples called him with an address for the meeting: 1740 Collingwood, Apartment 211. Be there at 3 p.m. Levine wrote the information down on one of the book’s pink betting slips.

That afternoon, the four men left the book about 2:45 p.m. unarmed – it wouldn’t look good to go to a peace conference armed, after all.

Right on schedule the four men arrived at the Collingwood address, a quiet residential section on the city’s West Side.

Ray Bernstein met the men at the door of the apartment. As they entered the apartment, one of the other men turned off a phonograph, leaving the needle in the middle of the record.

"Ray said he was glad to see us," Levine said later. "(Irving) Milberg and (Harry) Keywell were there too and so was Harry Fleisher."

The baby-faced Keywell was a tough customer whose innocent looks belied a hard interior. He had been accused but acquitted of illegal possession of firearms and assault with intent to do great bodily harm earlier in the year. Keywell was also named as a suspect in the St. Valentine’s Day Massacre.

It was a surprise to see Fleisher, because the feds were looking for him and the word on the street was that he had taken it on the lam. Fleisher, 29, was a slightly built killer whose rapsheet listed such crimes as assault with intent to kill, armed robbery, kidnapping and receiving stolen property.

Milberg’s record spanned more than a decade and included everything from armed robbery to disturbing the peace. He was known as a crack shot.

After the rival gangsters exchanged greetings, Paul, Levine and Lebowitz sat next to each other on a couch and Izzy took a seat on the arm. They chatted amicably for a few minutes.

Fleisher looked at Bernstein and asked, "where is that guy with the books?" referring to their accountant. Bernstein said something about going to look for him and left the apartment. Bernstein went down to the street where the Purples had a car waiting. He started the engine, raced the engine loud enough to irritate several neighbors nearby and laid on the horn.

"That was the signal," Levine recalled. "Fleisher pulled out his gun and fired at Nigger Joe and the bullet went right by my nose."

At the same time, Milberg and Keywell fired at Sutker and Hymie Paul.

Approximate body positions of Sutker, et al.

The hail of gunfire had caught the trio by surprise, but it was apparent from the positions of their bodies that they had tried to get away. Paul lay slumped against the couch in the living room with eight bullets in his back and head a cigar still clenched in his hand, Lebowitz was sprawled in a short corridor leading to the bedroom, a battered cigar stub in his teeth. Izzy Sutker died in the bedroom of the apartment, two bullet holes not more than an inch apart in his forehead, a stogie in his hand.

The three young hoodlums fell far short of their goal of making it big in the rackets. Izzy had 11 cents on him, Hymie had $2, and Lebowitz died with $92 in his pocket.

Fleisher turned to Levine, who was astounded that he was still alive, and asked "You OK?" Levine nodded mutely, waiting for his execution.

The three killers huddled for a moment and then turned to Levine. "Let’s go," one of them shouted. The four men ran to the kitchen, where Fleisher, Milberg (whose sharpshooting had dropped Izzy) and Keywell, a murderer who had yet to attain voting age, dropped their .38 caliber revolvers into a bucket of green paint.

The paint destroyed any chance the cops had of pulling fingerprints from the pistols. The killers had taken pains to cover their tracks; they had filed the serial numbers from the Colts, as well.

Levine, Milberg and Keywell joined Bernstein in the big, black 1930 Chrysler. Fleisher arrived a few moments later after the men heard more shots from the apartment.

"Nigger Joe was still living a bit," he told them.

A young mother, trying to put her baby down for a nap heard the commotion and rushed out into the hall, encountering Fleisher on his way to the car.

the gunmen's escape route

"The man was taking the steps two at a time toward the alley," she told the Detroit Times.

The Chrysler sped out of the alleyway behind the Collingwood apartment, nearly running over a small boy playing in the street and the sister of a Detroit Probate Court judge.

"They shot away so fast the driver burned his tires on the alley pavement," said apartment caretaker Harry McDonald, who witnessed the escape. "Walking to the car the men moved quickly but they did not seem excited."

The killers "drove like the devil" for a few blocks, Levine said. Then they split up.

"Bernstein shook hands with me and said, ‘I’m your pal, Solly.’ He gave me three or four hundred dollars and said go back to the book and he’d pick me up later."

Solly Levine did go back to the book, unaware that the Purples weren’t done with him. Bernstein planned to take him for a ride later and frame him for the murders.

Crowd gathering outside Collingwood Manor apartments

But the heat came down fast after the killings and inside an hour Levine was in police custody.

He told police that he and the three dead men had been kidnapped while on their way to talk to well-known Detroit bootlegger Harry Klein, owner of a local deli and friend of the Purple Gang.

"I give you my word," Levine told the Times. "I didn’t see anyone."

Police quickly discounted Levine’s kidnapping story after he failed to tell the tale the same way twice.

Lawmen quickly set up a dragnet to find the killers, and Wayne County Prosecutor Harry S. Toy told reporters he wanted to find the gunmen "dead or alive."

Toy issued orders for the roundup of all Purples and reportedly ignored overtures from Purple chiefs who said they were willing to surrender.

"There will be no deals," he said. "We’ll go and get them."

One of the first people arrested in connection with the murders was Klein, who was carrying one of the dead men’s markers. Klein denied knowing anything of the crime or of a planned meeting with Izzy Sutker and was eventually freed.

The heavy police dragnet yielded results in less than 48 hours.

"We got scores of telephone calls giving us valuable information as soon as we released the names of the killers," Toy said.

The tips likely came from enemies of the Purple Gang, with the underworld leaping to take advantage of an opportunity to rid itself of their domination.

Acting on an anonymous tip, heavily armed police surrounded an apartment owned by Charlie "The Professor" Auerbach, who listed his occupation as jewelry salesman. Inside, Ray Bernstein and Harry Keywell were holed up with Auerbach, his wife and an 18-year-old cabaret entertainer named Elsie Carroll. The Detroit Times identified her as "a smartly dressed, flip-cracking blonde, said to be the sweetheart of Izzy Bernstein."

The women were carrying more than $9,000 in cash and police found tear gas and guns in the house.

The gangsters were reportedly quite sullen when they were brought into police headquarters.

"Ray Bernstein’s snarl and swagger left him," the Detroit Times wrote. "Detectives said he appeared nervous."

The next day, Irving Milberg, whose receding hairline belied his years, joined his gang behind bars when authorities staged a raid on Milberg’s flat on West Chicago Boulevard. While they were there, Milberg’s wife, Mildred, called the house, where a maid was watching her children. The call was traced to Purple Gang gunman Eddie Fletcher’s apartment three blocks away.

When authorities burst into Fletcher’s apartment they found Abe Axler, Milberg and Eddie Fletcher playing cards, a packed suitcase in Axler’s car and five pistols and a rifle at the ready. The men surrendered without a fight, although Milberg tried to escape by flinging open a window and punching out a screen.

The killers were in custody.