Tag Archive for Detroit

The Color Purple

Collingwoord Manor Massacre as illustrated by Detroit Times

Note: Contains language that some may consider offensive.

The Detroit River, representing the border between Ontario, Canada, and the United States, is one of the busiest waterways in the world, with freighters bringing iron ore from Michigan’s Upper Peninsula to the bustling automobile factories of the Motor City. Timber barges from northern Michigan and Wisconsin pass through the narrow waterway which separates Windsor, Canada and Detroit, Michigan en route to Lake Erie and the East Coast and hordes of recreational boaters and weekend fishermen use the river for their pleasure.

In the winter, traffic on the narrow flow (less than a mile across in some places) comes to a halt as the river freezes over.

During Prohibition, rumrunners and bootleggers used the frozen river as an easy way to get booze from Canada into the United States. From Detroit liquor went to Chicago (where Capone sold it under his “Log Cabin” label), St. Louis, and points west.

It was a well-known fact that if you were bringing a load of hooch across the Detroit River you had better show up armed to the teeth. Because in the 1920s, Detroit belonged to the Purple Gang, a group of killers and thugs as vicious and bloodthirsty as any racketeer in New York or Chicago.

The Purples ran the rackets in Detroit for much of the 1920s and early 30s until the Syndicate boys from back east moved in and wrested control from a gang that had seen its numbers decimated by infighting and prosecution.

Detroit may not have been New York, but make no mistake: the Purple Gang was tough. They were strong enough to tell Capone to keep his mitts off eastern Michigan and managed to hold on to control of most of the state when Scarface was at his peak: U.S. 31, which cuts the gut of Grand Rapids and runs from the top of the mitten to the Indiana border (and down to the Gulf of Mexico) was the territorial line. West of 31 was Capone’s territory but east belonged to the Purples. Capone coveted Detroit, with its huge number of hardworking, hard-drinking laborers, but wisely decided it was better to buy and sell booze with the Purple Gang than to fight them.

Bootleggers in Detroit had a jumpstart on much of the nation, when Michigan passed a state prohibition on liquor in 1916 effective the next year. Henry Ford, whose River Rouge plant employed more than 100,000 people at its peak, was a leading proponent of a sober workforce. His workers, however, had other ideas.

What Ford and the other teetotalers didn’t take into account was the city’s close proximity to borders with Ohio and Canada. When Prohibition went into effect in Michigan with the passage of the Damon Act in 1917, the spigots on illegal booze were turned on. Anyone with a boat could get to Canada and friendly Toledo, less than 60 miles south of Detroit, was more than willing to meet the needs of thirsty Detroiters.

“False floorboards in automobiles, second gas tanks, hidden compartments, even false bottomed shopping baskets and suitcases, not to mention camouflaged flasks and hot water bottles were all employed as the entrepreneurial and the thirsty navigated the Dixie Highway between Detroit and the Ohio border,” wrote Jenny Nolan in The Detroit News. “It was a sort of dress rehearsal of ingenuity and audacity for the much larger operations to come.”

Judges took a lenient view of offenders, and in 1919 the Damon Act was declared unconstitutional. Traffic between Michigan and Ohio returned to normal and for a short time the tables were turned as Ohio outlawed the manufacture and sale of liquor.

But anti-liquor fever ran high in those days. When the Volstead Act became law in 1920 and Prohibition was the law of the land, rumrunners in Detroit were ready.

Canada replaced Ohio as the favorite travel spot for Detroiters. Although Ontario had outlawed the retail sale of liquor, the federal government approved and licensed distilleries and breweries — of which there were 45 in Ontario alone in 1920 — to manufacture, distribute, and export booze.

“With the Detroit River less than a mile across in some places, and 28 miles long with thousands of coves and hiding places along the shore and among the islands, it was a smugglers dream,” wrote Nolan. “Along with Lake St. Clair and the St. Clair River, these waterways carried 75 percent of the liquor supplied to the United States during Prohibition.”

Cargo was towed beneath boats, old underground tunnels were built, sunken houseboats hid underwater cable delivery systems, and even a pipeline was built. Between Peche Island and the foot of Alter Road, an electronically controlled cable hauled metal cylinders filled with up to 50 gallons of booze. A pipeline was constructed between a distillery in Windsor and a Detroit bottler.

Illegal liquor was the second biggest business in Detroit at $215 million a year in 1929, just behind automobiles. During Prohibition, the trade in alcohol employed about 50,000 people in the Detroit area, according to The Detroit Free Press. There were as many as 25,000 blind pigs operating in the Detroit area, and authorities were not only helpless to stop it, many were part of the problem.

Nick Schaefer ran a blind pig across the street from Police Headquarters, above a bail bondsman’s office. Reporters and police alike frequented the place for its famous potato soup and free lunch.

When the state police raided the Deutsches Haus at Mack and Maxwell, they arrested Detroit Mayor John Smith, Michigan Congressman Robert Clancy and Sheriff Edward Stein. From St. Clair Shores’ Blossom Heath on Jefferson to Little Harry’s downtown, to the Green Lantern Club in Ecorse, Detroit’s most upstanding citizens fed the coffers of the gangs that were reaping huge fortunes from their appetite for alcohol.

With such a demand for booze, it wasn’t long before organized groups took over from informal rumrunners. The Licavolis, Bommaritos, Lucidos and Zerillis brought a Sicilian flavor to east side efforts, while the Tallman gang led the West Side.

The one group who had the run of the town was the Purple Gang.

“Like Rotten Meat”

Like most other big cities around the turn of the century, Detroit’s ghettos were a breeding ground for crime and violence. The Purple Gang’s evolution isn’t much different from a dozen similar stories from any American city. They were really no different than the Five Points Gang in Brooklyn, the Northside Gang in Chicago or the Boiler Gang in Philly.

Rumor had it that the gang received its colorful name as the result of a conversation between two Hastings Street shopkeepers of the era. Both of the men’s shops had been the target of the youngsters’ shoplifting and vandalism forays. One day in disgust one of the shopkeepers exclaimed, “These boys are not like other children of their age, they’re tainted, off color.”

“Yes,” replied the other shopkeeper. “They’re rotten, purple like the color of bad meat, they’re a Purple Gang.”

In the beginning, the “gangsters” were nothing more than the sons of Russian Jewish immigrants who had come to the New Country in search of a better life. But like so many others, the immigrants found life in the United States wasn’t that different and that the streets really weren’t paved with gold.

The Purples, growing up in almost unimaginable poverty, began to prey on their fellow immigrants.

“The boys snatched ice cream, gum, candy, cookies and fruit from hucksters and stores,” wrote one Detroit Free Press writer at the time. “They ganged up on children their own age, sometimes they strong-armed grownups.”

The boys, led by the four Bernstein brothers – Abe, Joe, Raymond and Izzy, were shakedown artists and jewel thieves, but thanks to Prohibition and the convenient location of Detroit, the young delinquents quickly graduated from nuisance types of street crime to armed robbery, hijacking, extortion, and other strong arm work. They became notorious for their high profile manner of operation and their savagery in dealing with enemies.

By the early twenties, the Purples had developed an unsavory reputation as hijackers, stealing liquor loads from older and more established gangs of rumrunners

“The Purple Gang always preferred hijacking to rumrunning and their methods were brutal, wrote Paul Kavieff in his book on the gang, Off Color. “Anyone landing liquor along the Detroit waterfront had to be armed and prepared to fight to the death as it was common practice for the Purples to take a load of liquor and shoot whoever was with it. In the early years, the Purple Gang preyed exclusively on other underworld operators, insulating them from the police.”

The young Purple Gangsters attracted the attention Charlie Leiter and Henry Schorr, two Mustache Petes who operated the Oakland Sugar House on Oakland Avenue. Leiter and Schorr used the Bernsteins and their compatriots like George F. Lewis, Abe Axler and Eddie Fletcher for strong-arm work extorting businesses and leaning on back-alley brewers.

Inspector Henry J. Garvin, head of the Detroit crime and bomb squad, called the Purple Gang the ruler of the city’s underworld through terrorism. The Purple Gang of 1928, however, was not wholly composed of the “off-color” gang of the Hastings street hoodlums of 1918. The new group had been in existence only two years. But its leaders, Inspector Garvin declared, were the same boys who ruled the gang that plagued the ghetto merchants and hucksters.

In its rank and file were recruits from New York, St. Louis and Chicago. It was organized in 1926, Garvin said, as a defensive measure against the “St. Louis Gang,” which had invaded Detroit shortly before the kidnapping, in March 1926, of Meyer “Fish” Bloomfield, a stickman at the Grand River Athletic Club, Charles T. “Doc” Brady’s casino. Doc Brady paid fifty grand for the return of his employee. This was the first of a long series of kidnappings of gambling house operators for ransom.

The first act laid against the new Purple Gang was the triple slaying in the Milaflores Apartments, in March 1926, when Frankie Wright, Reuben Cohen and Joseph Bloom were killed by machine gun fire in an apartment occupied by Axler and Fletcher. Fred “Killer” Burke, famous for his role in the St. Valentine’s Day Massacre in Chicago in 1929, was hired by the Purples as the machine gunner.

Wright, Bloom and Cohen were gunned down as they waited to enter the Axler-Fletcher apartment, where they had been invited to a “peace conference.” The St. Louis gunsels were slain, it was reported at the time, because of a double-cross laid on the Purple Gang in the kidnapping of Fish Bloomfield. Although arrests were made, no one was ever convicted of the Milaflores slayings.
In the killings, the Purples became the first criminals in Detroit to use Thompson submachine guns. After they mowed down their three rivals, newspaper reporters counted 110 bullet holes.

The Cleaners and Dyers War

As the gang grew in size and influence, they began to hire themselves out as mercenaries, taking part in the Cleaners and Dyers War, keeping union members in line and harassing non-union independents. Bombings, thefts, beatings, and murder were all methods employed by the Purples to enforce union policy. They were paid handsomely for their services.
Purple Gang arrested during cleansers and dyers war

Virtually all the bombing outrages in that warfare were ascribed to the gang by the police.

In 1928, Charles C. Jacoby, vice-president of Jacoby’s French Cleaners & Dyers, Inc., and nine alleged members of the Purple Gang, were arrested and charged with conspiracy to extort money from Detroit wholesale cleaners & dyers. Besides Jacoby, the defendants included Abe Bernstein, Raymond Bernstein, Irving Milberg, Eddie Fletcher, Joe Miller, Irving Shapiro, Abe Kaminsky, Abe Axler and Simon Axler.

When the police concentrated their efforts on the Purple Gang, shutting off its source of revenue, it formed an alliance with the Oakland Sugar House Gang which had engaged in bloody warfare with other gangsters over tribute from distillers and bootleggers and others associated with the liquor racket.

The Purples ordered the Sugar House Gang to raise money for their defense fund by putting a tax of 55 cents on every 100 pounds of sugar sold to distillers. Other merchants were terrorized into paying tribute when the sugar tax did not raise enough revenue. Then the police raided the Sugar House Gang. Joseph Bernstein, brother of Abe Bernstein, alleged leader of the Purple Gang, was one of those arrested.

In explaining why the police had been unable to break up the Purples, Garvin said that the gangsters preyed only on racketeers and had the underworld so terrorized that no one dared to “squawk.” Hence, he said, the police were unable to get anyone to sign a complaint against them.

Taking of testimony in the extortion trial relating to the Cleaner and Dyer wars started before Judge Charles Bowles and a Recorder’s Court jury June 4, 1928. The State called 42 witnesses. A month’s adjournment was necessitated by the illness of Judge Bowles. Early in September, 1928, the case came to an end when the jury acquitted Jacoby and the alleged gangsters. Then Frank X. Martel, president of the Detroit Federation of Labor, was charged with extorting money from the Jacobys, and he, too was acquitted.

An acquittal wasn’t surprising in the case. After all, “someone” had broken into the Cleaners and Dyers Union offices shortly before the trial and stolen the documents that could have proved the extortion case. No arrests were made in the break-in.

“Also to members of the gang the police ascribed the deaths of Sam Sigman, of the Perfect Cleaners and Dyers, two and a half years ago, and of Sam Polakoff, of the Union Cleaners and Dyers, whose bullet-riddled body was found one morning at Dexter Boulevard and Grand Avenue a little more than a year ago,” according to a 1929 Detroit News article about the gang.

Police also blamed the gang for the slaying of Patrolman Vivian Welsh, “who was taken for a ride.”

“Welsh according to the Homicide Squad, had been ‘shaking down’ blind pig owners and in doing so had unwittingly invaded the field of the Purple Gang,” the News wrote.

During the late twenties, the Purple Gang reigned supreme over the Detroit underworld, controlling the city’s vice, gambling, liquor, and drug trade. They also controlled the local wire service which provided horse-racing information to all of the Detroit horse betting parlors and handbooks.

The gang members, now at the top of the food chain in the Motor City, cavorted with some more infamous mobsters, branching out into other cities, as well. Abe Bernstein was a friend of Meyer Lansky and Joey Adonis, with whom he owned several Miami gambling casinos. Bernstein also did a big favor for Capone.

On February 13, 1929, Bernstein called Bugs Moran and told him a hijacked load of booze was on its way to Chicago.

Moran, who was in the middle of a turf war with Capone, had only recently begun to trust Bernstein, who had previously been Capone’s chief supplier of Canadian liquor.

The two hoods agreed on a price of $57 a case, according to Jay Robert Nash in his book Bloodletters and Bad Men.

“Deliver it to the garage,” Bugs told Bernstein. “All the boys will be here. We’re short and they’ll want a cut.”

The next day, instead of delivering a load of liquor, five men dressed as cops went to S.M.C. Cartage on North Clark Street – Bugs’ Northside hangout – and opened fire with machine guns, killing seven men in what has become known as the St. Valentine’s Day Massacre.

The Collingwood Manor Massacre

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.

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 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.

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.

The End of the Purples

The gunmen were quickly bound over and a little over a month after the massacre, in a packed courtroom, Milberg, Ray Bernstein and Keywell were put on trial.

The Purples spared no expense in trying to save their members. The defendants’ cronies reportedly were squeezing money from local bookmaking operations, who were compelled to contribute $2 per day for “betting service.”

Solly Levine remained the key witness for the prosecution and despite the best efforts of defense attorneys stuck with his story that the three men killed his friends.

Prosecutor Toy led the case himself, summarizing the case before the jury:

“I hold no brief for the victims and their occupation. This is no defense, however. These men checked their books with bullets and marked off their accounts with blood. They lured the victims to the apartment with promises of partnership and killed them when they were unarmed and helpless.”

After an hour-and-a-half of deliberations, the jury returned guilty verdicts against all three men.

The verdict caused an eruption in the courtroom. Friends and relatives of the killers screamed hysterically and court officers climbed on tables to restore order.

A week later, Judge Donald E. Van Zile sentenced the three to the mandatory life in prison without parole. Shortly afterward with little fanfare, Ray Bernstein, Irving Milberg and Harry Keywell boarded a special Pullman train bound for Michigan’s Upper Peninsula to begin serving their sentences in the state’s maximum security prison in Marquette.

Harry Fleisher remained on the lam until 1932, but he was never convicted in connection with the massacre. He did serve time in Alcatraz in the early 1950s for armed robbery of an Oakland County gambling house.

Milberg died in prison after serving seven years

Harry Keywell had a spotless prison record for 34 years before his life sentence was commuted. He walked out of prison on October 21, 1965 and later married, obtained a job and faded into obscurity.

Ray Bernstein suffered a stroke in 1963 and was transferred to the state prison in Jackson. He was paralyzed in the left side and his speech was impaired when, wrapped in a blanket and in a wheelchair, he was brought before the parole board.

Bernstein, still denying his role in the massacre, was a model prisoner. He had no misconduct during his term and taught school to inmates after he received his own high school diploma. He also was known for giving financial assistance to other inmates.

The board gave him mercy parole in 1964 and he died two years later.

Solly Levine got a life sentence of another sort.

Fleeing the vengeance of the remaining Purple Gang members, Levine was put on a boat to France by police. However, when he landed in Le Havre, the government wouldn’t take him and sent him back. He then tried to go to Ireland, but couldn’t get a passport.

He then disappeared.

“It would be hard to tell whether or not Solly escaped successfully,” Judge Van Zile said in 1940.

Other members of the Purple Gang died as they had lived. Abe Axler and Eddie Fletcher were taken for a ride when Lucky Luciano’s East Coast Syndicate moved into the city. As the national crime syndicate began to consolidate the underworld in the mid 1930s, the remnants of the Purple Gang were absorbed.

The convictions in the Collingwood Massacre “broke the back of the once powerful Purple Gang, writing finis to more than five years of arrogance and terrorism.,” said Detroit Police Chief of Detectives James E. McCarty. “The effect of Bernstein’s conviction should be a great influence. He reached the top of the underworld and all it got him was a life sentence.”

Death of a Bootlegger

A bitter March wind was blowing in from the icy Detroit River through the gaps between the warehouses on Third Avenue as Jake Trager emerged from the Hastings Street blind pig. It was early afternoon, but the sun was already sitting low in the west, visible as a bright white ball through the gray clouds that sat in a seemingly eternal vigil over the city. Michigan was on the edge of the Eastern Time zone and evening came early during the winter months.
A handsome, thirty-something New York native, Jake had been in Detroit for several years now, but he had never gotten used to the endless string of colorless days that marked winter in Michigan. It seemed that sometime around late October when the rains came the blue skies headed south with the birds only to return in May. The sun’s periodic appearances over the long winter were in sharp contrast to the frigid temperatures.
The neighborhood didn’t offset the drabness of the weather, either. This was one of the more industrial areas of a city that was the epitome of the factory town. As far as the eye could see the only variation to the hues of gray were the occasional white piles of nearly melted snow and the brown patina from the warehouses which lined both sides of Hastings Street, one of the thousands of cobblestone thoroughfares in Detroit.
In the distance, Jake could hear the occasional bell from a freighter making the trip up the mile-wide Detroit River, which separated the city, Michigan and the United States from Ontario, Canada. The ships had just recently started navigate the waterway. The river froze over in the winter, making the busy waterway impassable from November to March. Coast Guard icebreakers started chopping up the main channel a few weeks before so the iron ore freighters could once again move through the river into Lake Erie.
Despite the best efforts of the icebreakers, winter refused to release its grip on the river and forced the Coast Guard to reopen the same stretches repeatedly. The return of spring meant many things to Jake, not the least of which was the need to find himself a reliable boat to make the trek across the river to meet his friends in Windsor. It had been several weeks since he had dared make the trip across the ice in his Stevens, for several of his cronies had already reported cracks in the ice that made driving across the river even more dangerous than usual. Since the Coast Guard cutters had moved through, Jake had been relying on American made product to supply his customers, but they were clamoring for the better Canadian stock and he risked losing his clientele unless he could find some way of getting across to Ontario. The cutters served two purposes: first, to open the shipping channel for the big boats, and second to keep an eye out for bootleggers brazen enough to brave the early spring chill in their mad dash across the river to Canada.
Jake had come west shortly after the passage of the 19th Amendment to the U.S. Constitution became law in 1919, making the United States, on the surface at least, a dry nation. Jake was a smart man and before Prohibition became the law of the land he had already made contacts in Michigan with people on both sides of the law who were interested in continuing to ensure that the Detroit workingman had access to booze. Michigan had already experimented with Prohibition in the mid-teens, outlawing the sale and manufacture of liquor so that Henry Ford and the other entrepreneurs could be assured of a sober workforce. The state’s version of the Volstead Act had been declared unconstitutional, but not before hundreds of bootleggers like Jake Trager honed their skills in distilling or importing illegal booze. When the rest of the nation went dry shortly afterward, rumrunners like Jake Trager were ready for business.
Along with his brother, Willie, and friends Benny Glass and Louis “The Wop” Ricciardi, Jake founded the Saw Still Gang, which operated near Detroit’s Eastern Market, supplying booze to private citizens, blind pigs, restaurants and other bootleggers in a wholesale market. Jake had quite a reputation among bootleggers in Detroit, which, thanks to its ideal location, controlled the lion’s share of the illicit booze importation market in the United States. He worked alongside the Oakland Sugar House Gang, arguably the city’s most powerful gang in 1923, and the bloodthirsty and ruthless Purple Gang, which was in the early 20s emerging as a force to be reckoned with in the nation’s underworld.
The Purples, led by the Bernstein brothers, were still in a transition phase, no longer pulling the strong-arm punk rackets, but not yet commanding the fear and respect which they would earn during Detroit’s bloody Cleaners and Dyers War a few years hence. The Purple Gang, under the direction of the leaders of the Oakland Sugar House Gang, had developed a habit of knowing just when and where the next shipment of booze was coming across the river and showing up armed to the teeth to hijack the hooch. This strategy of robbing and silencing other bootleggers helped them gain a great deal of power without coming to the attention of either the federal revenue agents or the Detroit police. After all, no bootlegger was going to complain to the law about a lost batch.
Prohibition had been very good to Jake and the rest of the Saw Still Gang. He had developed a national reputation and remained close to his East Coast friends, Salvatore Lucania, a.k.a. Charlie Luciano, Irving “Waxey” Gordon and Meyer Lansky. The heart of the “Bugs and Meyer Mob,” Lansky, Luciano, Benny Siegel and Francesco Castiglia — who would later come to run the New York underworld using the name Frank Costello – were easily a dozen years younger than Jake Trager, but their youth was no impediment. The Bugs and Meyer crew rivaled any of the more experienced New York criminal enterprises, thanks to the backing of Arnold “The Brain” Rothstein. Visiting the Big Apple on a regular basis for “business” meetings, Jake would return to the old Willett and Rivington neighborhood like a conquering war hero, driving into Little Italy in his Stevens-Dureya touring car, which marked him as a powerful man to the immigrant residents.
From everywhere, youngsters would flock to the Stevens with its bright brass running lamps and dual spare tires. For a penny or two, Jake would hire a couple of youths to guard the car against the curious onlookers who might be interested in a souvenir while he sat inside a Willett Street pool hall hammering out important matters with his New York friends.
One of Jake’s regular car guards was a young tough who would later adopt the name Johnny Spinoza. Johnny had attended P.S. 34 with Luciano, Siegel, Lansky and Costello, although the Bugs and Meyer crew was several grades ahead of him. More importantly, Johnny was Jake Trager’s nephew and was following his uncle’s example. Like the Bugs and Meyer gang, Johnny and his friends got their start in crime almost as a defense mechanism against the severe poverty and brutality that marked Little Italy and its environs in the early 20th century.
Jake’s sister – Johnny’s mother – was married to another important New York racketeer, Anthony Carfano, who was known on the street as Little Augie Pisano. Little Augie was tight with Luciano and Vito Genovese, serving as a capo regime in Genovese’s organization for many years. Known to the public and the police by his street name, Carfano preferred to be called “Gus” by his friends and family. Carfano was also close to Johnny Torrio, the one-time boss of Chicago, whose protégé, Al Capone, was now arguably the most famous mobster in the United States. In fact, Jake’s presence in Detroit was partly because of Capone’s position in the Windy City.
Standing on the corner of Hastings and Wilkins streets in Detroit, Jake was joined by his brother and Benny Glass. The three men stood some distance apart from each other, not talking, their collars pulled up and their wide-brimmed hats pulled low against the cold wind. Growing out of the corner of his mouth, Benny’s ever-present nickel cigar gave off a cloud of smoke that hovered around his head and somewhat obscured his face. Jake gave Willie a stare that matched the icy temperature. Willie was a good man, but he had a weakness that Jake couldn’t understand and for which Jake had recently lost patience. Willie liked to bet; he would place a wager on almost anything, which in and of itself wasn’t so much of an issue. The problem was that Willie couldn’t pick the winner in a two-horse match race, and he tended to bet money he didn’t have. Willie liked to live large, and he spent his portion of the Saw Still profits faster than Jake, the group’s treasurer, could pass them out.
In recent months, Jake had bailed out Willie more times than he cared remember and it was starting to take its toll on their relationship. They were brothers, and Jake had always promised to look out for his younger sibling, but Willie didn’t seem to care that he was taking advantage of his brother’s filial concern. More than once Jake had told Willie he wasn’t going to continue to cover his bets, and yet Willie would come back within days with another lame excuse. Now, the handbook operators weren’t even bothering to go to Willie to collect. They were going straight to Jake. No threats from Jake could make the Italian bookies stop taking his brother’s wagers.
Something would have to break, Jake thought to himself. The street was nearly deserted. It was too cold for the children of the tenement to be playing outside and the workingmen had not yet finished their labors. Vendors from the Eastern Market had already packed up for the day and only a few pushcarts remained. There were a number of automobiles around, mostly Fords and Dodges, with the occasional Hudson. One of the Dodge cars sat at the corner, its large-block engine idling roughly. Curtains covered the back windows, and no one except Jake could see who was seated behind the driver.
As Jake and Benny approached the car, the rear passenger’s side window was rolled down and the curtain pulled back slightly. Witnesses would tell police later that Jake and the passenger exchanged words in low voices – it did not appear the two men were arguing – before several shots exploded from the Dodge and Jake fell to the cold, wet cement, his head making a loud cracking sound as Jake’s lifeless body collapsed.
Living in a world of violence, Jake Trager would not normally have been gunned down under the conditions he found himself in. There is a very good possibility that Jake was double-crossed and killed by members of his own gang. Nevertheless, all it takes is one moment of carelessness for a bootlegger to drop his guard and pay the ultimate cost. Newspapers reported at the time that Jake, accompanied by Benny Glass, approached a car owned by Louis Ricciardi, had a brief conversation with the occupant (who was never fully identified) and fell under a hail of lead. His brother was standing nearby, although he was unable (or unwilling) to intervene.
There are two theories about why Jake Trager died on that cold Detroit street corner. The first is that he was rubbed out because he refused to cover one of his brother’s gambling debts and that Willie had agreed with the men who held his markers to turn over the Saw Still operation to them. Of course, the only thing standing in the way was Jake Trager. However, there is scant evidence to support this theory, and those who knew Jake and Willie refuse to believe one brother would sell out another like that.
The second, more credible, theory is that Jake was killed to send a message to his New York friends. Jake had been sent to Detroit specifically at the request of Al Capone, who was operating in Chicago, and Johnny Torrio, who had moved back east. In the Byzantine relationships between mobsters, it is possible to connect Jake Trager, Capone, Torrio, Luciano, Carfano, Ciro Terranova and of course the Bugs and Meyer mob. Luciano, Carfano and Terranova were all the forefathers of the Genovese family and as such were very tight. Capone and Terranova were cousins. Trager and Carfano were brothers-in-law.
Detroit was the lynchpin to controlling a nationwide bootlegging network. Capone needed a steady supply of Canadian booze and Jake Trager was tough enough to move into the motor city and take control. Many had tried to conquer Detroit since the beginning of Prohibition, but no one had really succeeded. Egan’s Rats, the St. Louis mob, had tried and had been rebuffed, the Purples had yet to rise to power, and the Licavolis and other Italians had not organized to the extent that they were powerful enough to dominate the entire city. Detroit was ripe for the picking by the New York Syndicate and Jake Trager was their point man in the city. That’s why he had to die. Jake’s murder made the front page of two of Detroit’s three daily newspapers, and his photograph was run in the Detroit Times. The Times reported that police from the city’s “Italian Squad” were looking for Ricciardi, who reported his car – identified as the murder vehicle – stolen. Ricciardi was later tracked down and arrested in Newark, New Jersey, but no further newspaper articles address any justice being done in Jake’s death. Further investigation of Jake Trager revealed one interesting fact: on his death certificate, Trager’s mother’s maiden name was Ricciardi. This begs the question of what relationship Trager and Ricciardi shared – if any. Were they brothers? Cousins? Louis the Wop disappeared into history and efforts to track him down have not met with success.
Jake Trager’s death soon faded from the public eye and the story of his violent end was replaced by another senseless crime on the front pages of the Detroit papers. After all, the city averaged almost one murder a day that year.