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St. Paul’s Gangster Era

By Robert O’Connor.

[This is Part Three of a series on the grittier history of the Twin Cities. Part one covered the rise and fall of Doc Ames, part two covered the O’Connor system in St. Paul and Prohibition.]

On February 14, 1929, St. Valentine’s Day, seven members of Bugs Moran’s gang were lined up against the wall of a warehouse on the North Side of Chicago. Their captors were waiting for Moran, but he never showed. Moran had controlled the North Side, while his rival, Al Capone, had controlled the south. By noon, the seven men were dead of 70 sub-machine gun blasts.

st-valentines-dayAftermath of the St. Valentine’s Day Massacre (Russell Hamm, Chicago Daily News)

Thousands of words have been written speculating about who carried out the St. Valentine’s Day Massacre. The event brought an end to Moran’s influence, spelled the beginning of the end for Capone and erased whatever public support was left for Prohibition.

By 1932, the Democratic Party and their candidate for President that year, Franklin Roosevelt, promised to repeal the 18th amendment. They succeeded with the ratification of the 21st amendment and “the noble experiment” ended on December 5, 1933.

From Chicago, Capone had controlled bootlegging operations across the country. He was one of many criminals of the era who captured the public imagination. Bootleggers were looked at as Robin Hood-like figures who brought banned alcohol to the masses.

Capone controlled bootlegging operations from his base in Chicago’s Lexington Hotel. Across the country were “safe cities” where organized crime operated freely. Reno, Nevada was where criminals laundered money. Kansas City’s political machine, led by Tom Pendergast, kept alcohol flowing.

St. Paul, Minnesota was where criminals could hide. The police there were still working under the O’Connor system. Their fixer was Harry “Dutch” Sawyer, the owner of the Green Lantern after “Dapper Dan” Hogan was assassinated. Sawyer was supposed to keep criminals in line, but he didn’t control the lesser vices in the city like gambling and bootlegging. That honor belonged to Leon Gleckman.

Bootlegging Boss

gleckmanLeon Gleckman (St. Paul Daily News)

Leon Gleckman was born in Minsk in 1894. He moved with his family at the age of nine to Port Huron, Michigan. Gleckman was a bootlegger and gambler in St. Paul in 1922 when he was arrested for the first time. His quickness to bribe elevated him to the top of the St. Paul underworld.

He was arrested again in 1927 and sentenced to a year and a half at Leavenworth for liquor conspiracy. When he got out, he turned Suites 301-303 of the St. Paul Hotel into his personal offices. From there he controlled almost all of the gambling in the city and most of the bootlegging. The circle at the front door became a drop-off point for the bootleggers in the city.

Gleckman expanded his criminal empire by bribing politicians and purchasing stakes in companies such as the Republic Finance Company. He was at the height of his powers between 1930 and 1932, when his friend Tom Brown was the Chief of Police. Brown had been a friendly cop since his days as a detective, and facilitated Gleckman’s operations while chief. Under his reign, police didn’t recognize the faces on the FBI’s most wanted list, and when conducting a raid the police (thanks to Sawyer) would call their targets ahead of time to warn them.

Gleckman was kidnapped on September 24, 1931 and held in a cabin in Wisconsin for three days. The culprits demanded ransom of $200,000, but very quickly dropped it to $5,000 plus the cash Gleckman had in his pocket. Chief Brown worked fiercely to trace down the kidnappers. Jack Peifer, owner of the Hollyhocks casino and Gleckman’s rival, was suspected as the man who funded the culprits, but he worked with the police to free Gleckman. One of the kidnappers, Frank LaPre, was later found dead by gunshot and the ransom was recovered from his hotel safe. Brown used the money to run (unsuccessfully) for Ramsey County Sheriff. It’s also alleged that Homer Van Meter, a member of John Dillinger’s gang, contributed $1,000 to his campaign.

Brown had been appointed Chief in 1930 after several years as a detective. He publicly promised to drive out gangsters, but in private continued the O’Connor system

Gleckman was, and is, called the Al Capone of St. Paul, and coincidentally was brought down by the same crime. In 1934, Gleckman was sent to prison for good for tax evasion after having been investigated by the same men who nailed Capone.

After his kidnapping, Gleckman volunteered to help the police in later kidnappings, ones that later became the concern of Federal authorities soon after.


On March 1, 1932, the son of aviator Charles Lindberg Jr. (a Minnesota native) was kidnapped. The sensational coverage of the kidnapping and the trial of the accused kidnapper, Bruno Richard Hauptmann (who maintained his innocence until his execution) was so over the top that H. L. Mencken called it the “biggest story since the Resurrection.”

In response to the crime, Congress passed and President Herbert Hoover signed the Federal Kidnapping Act, which made it a federal crime to transport a kidnapping victim across state lines. The responsibility for pursuing the victims and the perpetrators was given to the Bureau of Investigation, renamed the Federal Bureau of Investigation in 1935, and its director – J. Edgar Hoover.

Around the same time, Kate “Ma” Barker and her criminal sons had already become infamous for their spectacular bank robberies and murders committed across the Great Plains. When they first stayed in St. Paul, they lived at the Commodore Apartments, where F. Scott and Zelda Fitzgerald had lived several years earlier. They were plotting their next move in early 1933 when Jack Peifer suggested a kidnapping victim:  William Hamm Jr.

William Hamm Jr. had taken over the Hamm Brewery in 1931 after his father (who had been a close associate of R. T. O’Connor) had passed away. The brewery survived in prohibition by making non-alcoholic drinks.  On June 15, 1933, Hamm was walking back to his home, where his mother had lunch waiting for him.  He was approached by a man on the side walk. “Mr. Hamm,” the man said, reaching his hand to shake.

When Hamm grabbed it, the man, Charles Fitzgerald, forced him to the ground as a car pulled up.  Hamm was thrust into the back seat.  In the car with him were “Doc” Barker and Alvin Karpis. They drove to a hideout in Illinois while other members of the gang negotiated a ransom – $100,000.

Their go-between was William Dunn, an associate at the brewery who ran a pool hall frequented by gangsters. Dunn paid the money and Hamm was set free after four days. He was dropped off in Wyoming, Minnesota in a vain attempt to make it look like he never left the state. The feds knew better. The gang sent the money to Chicago to be laundered, but Tom Brown – who had become the head of the Kidnapping squad after being replaced as police chief – warned the gang to flee. The feds had been tipped off by a neighbor.

A few months later, the extent of the O’Connor system was laid bare when the gang robbed a South St. Paul bank and made off with $30,000 after killing a police officer and wounding another. Brown got much of the spoils.

But the gang’s next big kidnapping would bring them down. Their next target was Edward Bremer, owner of the Schmidt Brewery in St. Paul. Schmidt had survived prohibition by making soft drinks, root beer and near beer. It also had an exclusive agreement with Dutch Sawyer to brew real beer that would be smuggled through a series of underground tunnels to the Green Lantern. Bremer also ran the Bremer Bank, where Leon Gleckman and Sawyer did their banking. Sawyer and Bremer had parted ways on alcohol and Jack Peifer suggested him as a target. Meanwhile, Tom Brown had dispatched officers to protect wealthy St. Paulites from kidnapping, but he gave the gang information on Bremer’s very precise habits that allowed them to strike.

And strike they did on January 17, 1934. The ransom of $200,000 was paid for Bremer several months later, but the feds stepped up their pursuit of the gang. Wealthy St. Paulites were horrified at the Bremer kidnapping, with many of them convinced that they were next. Many of them had connections with the Roosevelt administration and urged him to do something. The BOI had gained several new powers thanks to reforms at the Justice Department passed by Congress in the wake of the Kansas City Massacre. After they were passed, J. Edgar Hoover unveiled a list of “public enemies.” On that list were Alvin Karpis and Ma Barker.

barkerbodiesBodies of Ma and Fred Barker (Corbis)

Karpis was caught in 1935 and sent to Alcatraz – and would serve the longest sentence there.  Doc and Ma Barker were killed that same year in a shootout with the government.  For years, perhaps to justify the agency’s killing of an old lady, J. Edgar Hoover portrayed Ma Barker as a cunning, ruthless and inhuman criminal, while later autobiographies of Alvin Karpis and Harvey Bailey dispute these claims.

Dillinger’s Gang

Beginning in September 1929, people began losing confidence in stocks, despite attempts by large investors to demonstrate that the stock market was still viable. People lost confidence in their banks, since there was no protection against bank insolvency. Much of the Great Depression’s economic decline has been attributed to bank runs, when large numbers of people withdraw deposits from their bank.

To make sure these kinds of runs wouldn’t happen, FDR created the Federal Deposit Insurance Corporation (FDIC). The agency would guarantee insurance for deposits, reassuring people that if a bank failed, their money would be safe.

This also meant that banks could make loans more easily and would make depositors indifferent to robberies. The bank would lose money, but they would not.

Bank robbers would be sensationalized in the press, with many of them becoming idolized in the media – Bonnie and Clyde, the Barker-Karpis Gang, and John Dillinger.

By the time John Dillinger came to St. Paul, he was already a famous criminal. He had robbed a number of banks across the country, most notably in Indiana and Ohio. The BOI pursued him with a $20,000 reward for his capture, even though he and his gang hadn’t broken federal laws. He was finally caught in Tuscon in March 1934 and extradited to Indiana, but escaped by stealing the local Sheriff’s car and drove to Chicago – in an act known as the “wooden pistol” escape after an associate handed Dillinger the wooden pistol he used to threaten the guards and take them hostage.

While in St. Paul, he organized a new gang. Old collaborators of his like Homer Van Meter were still with him, along with new hands like John Paul Chase and Eddie Green – who were also associated with the Barker-Karpis gang. Through Van Meter and Green, Dillinger began collaborating with another famous criminal, whose gang had helped him escape from prison – George “Baby Face” Nelson. Like “Pretty Boy” Floyd, Nelson hated his nickname.

dillingerJohn Dillinger (FBI)

Dillinger returned to a life of crime, but this time the BOI was on his tail. The agency, lead by Melvin Purvis, pursued the gang members across the Midwest – almost killing Dillinger and Nelson as they rested at the Little Bohemia Lodge in Manitowish Waters, Wisconsin. It was after they escaped that the BOI added Nelson’s name to the public enemy list.

Dillinger was eventually shot outside the Biograph Theater in Chicago after another shootout with agents. Nelson was killed in a shootout with agents on November 27th in the town of Barrington, Illinois.

Newspaper scheme brings down the system

The extent of the O’Connor system was revealed by Howard Kahn, the editor of the St. Paul Daily News. He had crusaded against crime in the city for many years – in 1934 a grand jury looked into charges of corruption accusations leveled by Kahn and found nothing. Mayor William Mahoney said that St. Paul had no epidemic of crime and charged “if there are any gangsters here, it is because they have been invited by the newspapers.”

A month later, Mahoney was voted out of office and replaced by Mark Gehan, who had promised to “stop the pussy-footing and indecision” surrounding crime. Women groups, who had long protested crime, had raised awareness of the gangster problem to such a level that 74% of registered voters turned out to vote, the highest in the city’s history. Gehan won by 592 votes.

Gehan appointed Ned Warren as commissioner of public safety. Warren wanted to bring in Alexander Jamie to become Police chief. Jamie had been the chief investigator for the Secret Six – six business leaders in Chicago who had organized the business community against Al Capone and his empire. Jamie was turned away by the city council, who didn’t want to bring in an outsider. Warren appointed Michael Culligan to the post instead.

Still determined, Kahn hired Jamie’s 27-year-old son Wallace to do some sleuthing for him. Wallace had been trained in police administration and criminal detection at the University of Chicago and Northwestern University, and was given the chance to clean up the city. He tapped police telephones and placed dictaphones under prominent officials desks. Jamie then recorded all of this with a pamograph. He had been recording for four months when a janitor was cleaning a ventilation shaft and found one of the dictaphones and officials realized what was happening.

detectivePage one of “Young Detective Smashes Police Ring in the July 1936 issue of Modern Mechanix

The transcribed recordings took up 3,000 pages, which Warren gave to Gehan. The Daily News broke the story on July 24, 1935. Culligan resigned, while several detectives, officers, and others were convicted of a variety of crimes and sent to prison after a grand jury investigation.

The O’Connor system was over, and St. Paul was no longer a criminal haven. For many decades, it was an unspoken chapter in the city’s history. Gangster hang-outs were either demolished or replaced. The St. Paul Hotel lay in neglect for many years until it was refurbished in the 1980s. The Federal Courts moved and their building was renamed Landmark Center, which is now an arts and cultural center.

But recently there’s been an embrace of the era. The Wabasha Street Caves – a popular hideout – organizes tours with actors playing gangsters. Paul Maccabee’s book John Dillinger Slept Here tells the complete history of St. Paul’s gangster era (much more detailed than here) in the form of a travel guide.  The Minnesota Historical Society, which provided much of the information for Maccabee’s book, has also set aside a collection of materials related to the era.

St. Paul’s gangster era was over. But Minneapolis had its share of troubles during the era.

[Coming up in part four: Minneapolis’ gangsters. The newspapermen that crusaded against them and a landmark first amendment case.]

Robert O’Connor is a journalist, writer, adventurer and a few dozen other things (including a Co-Editor of 3:AM). His stuff has appeared in the Twin Cities Daily Planet, Hot Press, KFAI and a few other places. He lives in St. Paul, Minnesota.

First published in 3:AM Magazine: Monday, January 17th, 2011.