Crime, Corruption, and Saint Paul’s Connection to the Mob

Michael Waterston, Ordway 4/6/16

The Ordway’s final Musical Theater presentation of the 2015-2016 season, Bullets Over Broadway, tells the story of an ambitious young playwright who turns to the mob for help financing his first Broadway play in New York City. This interesting premise got us wondering about Saint Paul’s own ties to the mob.

We’re not the first to ask that question though. Local writer and journalist, Paul Maccabee, spent years pouring over more than 100,000 FBI files, wiretaps, and records to shed light on Saint Paul’s dirty, yet not-so-little, secret. In 1995, he published “John Dillinger Slept Here”. It’s a fascinating book, with a slightly misleading title, as it actually covers the depth and breadth of Saint Paul’s criminal history in great detail.

Quick Facts:

  • John Dillinger, Al Capone, Babyface Nelson, and the first-couple of crime, Bonnie & Clyde, are just a few infamous criminals who can all be traced back to Saint Paul at one point in their nefarious careers.
  • In 1932, Minnesota alone accounted for more than 20 percent of the nation’s bank robberies.
  • The Volstead Act (National Prohibition Act), which detailed the rules for enforcing the 18th amendment to the U.S. Constitution, was introduced by Minnesota Congressman Andrew Volstead.

Minnesota’s Capital of Crime

The bulk of Saint Paul’s most notorious criminal activity happened around the Prohibition Era (roughly 1920-1936); though the seeds were planted long before, and the effects remained for decades after.


Prohibition hit the nation like a wrecking ball. Led by the unyielding campaign efforts of groups like The Anti-Saloon League, Women’s Christian Temperance Union, Carrie Nation Prohibition Party, and even the Suffragettes. The belief was that a ban on booze would lower crime, strengthen families, and “generally improve the national character”.

Naturally, not everyone was on board. Almost as quickly as the ban on manufacturing, distributing, and selling of alcoholic beverages went into place, so too did the plans to illegally manufacture, distribute, and sell alcoholic beverages. Oddly enough, the 18th amendment made no mention of consuming alcohol to be illegal. Oops!

As for the idea that Prohibition would reduce crime, well, we all know how that turned out. Criminals like Al Capone built massive empires and networks that spanned the country, helping them profit to the (rumored) tune of $60 Million annually during Prohibition. Even your average, law-abiding citizens took to making their own “bathtub booze”, which often turned out to be extremely toxic, so the majority of people relied on “professional” bootleggers to do the dirty work.

The Layover Agreement

So, how were Saint Paul criminals allowed to thrive under the umbrella of Prohibition?

Minnesota’s capital city became a haven for criminals 20 years before Prohibition, when the Layover Agreement was put in place in 1900. Not an official policy or law, for obvious reasons, but that’s how corruption works – behind the scenes. The Layover Agreement is described in detail by, but it was essentially an unwritten arrangement between the newly appointed Chief of Police, John O’Connor, and any citizen of the criminal underworld. O’Connor created a system that would allow criminals to remain in the city and carry out their illegal activities on three conditions.

  1. Criminals were required to “check-in” with police upon their arrival. Presumably so that the police could keep track of their activities.
  2. Criminals must agree to pay the police a portion of their earnings. Yes, bribes.
  3. Criminals committed no “major” crimes in the city.

The arrangement worked out so well for all parties that the criminals even began “policing” themselves. If they caught wind of someone not playing by the rules, they’d rat them out to the cops. Too much heat on the criminals meant too much heat on the cops, which meant the whole operation would go belly up under the federal magnifying glass.

Bootleggers bastion

Local journalist, Walter Liggett, claims that during its peak, Saint Paul was home to over 10,000 bootleggers (hey, one for each lake!). During the 1920s, Saint Paul was a major railway hub that, with the help of the Layover Agreement, enabled bootleggers to move large quantities of liquor (often disguised as timber or kerosene) quickly and easily to all corners of the country.

Where everybody knows your name

The FBI tracked some of their most wanted criminals and gangs to the streets of Saint Paul, including Dillinger and the Karpis-Barker Gang, led by Alvin Karpis and Fred & Arthur “Doc” Barker.

In his autobiography, Karpis summed up Saint Paul’s reputation in the early 1930s. “Of all the Midwest cities,” he wrote, “the one I knew best was Saint Paul, and it was a crooks’ haven. Every criminal of any importance in the 1930s made his home, at one time or another, in St. Paul. If you were looking for a guy you hadn’t seen for a few months, you usually thought of two places—prison or Saint Paul.”

Popular stops on any criminals travel itinerary included the Green Lantern Saloon on Wabasha Street and Nina Clifford’s brothel on Washington Street. Leon Gleckman, the “Bootlegging Boss” or the “Al Capone of Saint Paul”, ran his business out of rooms 301-303 in the Saint Paul Hotel.

The end of an era

When Prohibition ended in 1933, so did the mutually beneficial relationships between cops and crook. No longer able to make a fortune off of illegal alcohol sales, the criminals turned to the next most lucrative option – kidnapping and ransom. After a string of high profile kidnappings, including Hamm’s Brewery president William Hamm Jr. and Schmidt Brewing Company heir Edward Bremer, the jig was up and the federal government set its eyes on Saint Paul.

If you’re curious about what life was like in Prohibition Era Saint Paul, stop by one of the Ordway bars and order The Bootlegger, a Prohibition-themed cocktail made with cinnamon whiskey, peach liqueur, and ginger ale.

Bullets Over Broadway | April 12-17, 2016


  5. Maccabee, Paul. John Dillinger Slept Here: A Crooks’ Tour of Crime and Corruption in St. Paul, 1920-1936. Paul: Minnesota Historical Society, 1995. Print.

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