This Random City Was A Literal Paradise For Prohibition Gangsters
This Random City Was A Literal Paradise For Prohibition Gangsters

This Random City Was A Literal Paradise For Prohibition Gangsters

Aimee Heidelberg - October 31, 2023

This Random City Was A Literal Paradise For Prohibition Gangsters
Postcard of Ramsey County Courthouse and St. Paul City Hall. McGhiever (2012, CC 3.0)

St. Paul Declared Crime Free

Around the time Dillinger set up residence at the Lincoln Court Apartments, the Ramsey County grand jury investigated claims that St. Paul’s police were riddled with corruption, and the city harbored the worst gangsters of the time. Ironically, on the day of the Dillinger shootout, a grand jury submitted their findings. The report claims, “We believe there is no justification for any charges that an excess of crime exists here.” They declared St. Paul did not have a serious crime problem. The newspaper St. Paul Pioneer Press called out the problem, asking “Why do these dangerous gangsters all head for St. Paul when they want to hide out from authorities or take a rest?” The ensuing outrage led to a campaign by the newspaper to raise money for better police weapons than just their pistols. The effort raised almost $2,000 for Thompson submachine guns.

This Random City Was A Literal Paradise For Prohibition Gangsters
Crowd outside Biograph theater in Indiana shortly after Dillinger’s death, 24 July, 1934. Public domain.

The Noose Tightens

By late July 1934, Dillinger was dead, shot by FBI agents outside the Biograph theater in Indiana. The FBI set its sights on the notorious criminals taking advantage of the St. Paul safe haven. Van Meter and the Barker-Karpis gang became the next targets. As the net tightened, the Barkers saw the winds of change. They left to find their fate elsewhere. But the gangsters were just a means to an end; they wanted to end corruption in the St. Paul police force. The FBI wanted to give St. Paul the actual clean bill of health the Ramsey County grand jury tried to give it on the day of Dillinger’s shootout. While the other gangsters laid exceptionally low, Van Meter lived openly in St. Paul. The underworld was growing concerned about Van Meter’s gallivanting. His handlers warned him about the FBI crackdowns, but Van Meter ignored warnings.

This Random City Was A Literal Paradise For Prohibition Gangsters
Homer Van Meter. FBI, Public domain.

Gangster Homer Van Meter’s final stroll

On August 23, 1934, just month after Dillinger died, Homer Van Meter went to the St. Paul Auto Company to consider buying a new car, possibly to leave town. He didn’t know there were four police officers lying in wait for him armed with shotguns. The shop, with its underworld connections, knew Van Meter would be there. As Van Meter left the shop and strolled down the street, the officers told Van Meter to stop. Van Meter ran into an alley, firing at the officers. Twenty-six shots hit Van Meter, some blasting off some of his fingers. Van Meter’s family would say the severity of his wounds (warning: link contains graphic content) made it seem to be an execution. The FBI indicated Harry Sawyer set Van Meter up. Sawyer allegedly wanted the money Van Meter was carrying, splitting it with the four officers involved in the shootout.

This Random City Was A Literal Paradise For Prohibition Gangsters
Landmark Center, served as Federal Courthouse from 1934 until 1966. w_lemay (2021, CC2.0).

St. Paul Wrecked it for the Rest of the State

After O’Connor’s death, his system lived on through two subsequent Police Chiefs. Minnesota accounted for more than 20% of the nation’s bank robberies, although this statistic was unsurprisingly lower in the city of St. Paul. But by 1933, the O’Connor system was eroding. The Hamm and Bremer kidnappings and the Dillinger shootout in 1934 happened within St. Paul borders, violating the terms of the agreement. The FBI caught and tried gangsters on federal charges. The FBI watched St. Paul law enforcement closely and exposed the corruption in the St. Paul Police Department. St. Paul’s mayor Mark Gehan and the new police chief Thomas Dahill declared a “war on hoodlums.” The O’Connor system was in turmoil, and with a police chief no longer on the take and criminals no longer being left alone, St. Paul was no longer the sanctuary city they had enjoyed during the O’Connor years.

This Random City Was A Literal Paradise For Prohibition Gangsters
Aerial view of St. Paul, c. 1930s. Joe Haupt, CC BY-SA 2.0.

How the O’Connor System Lasted for so Long

The O’Connor system lasted for about forty years, even after O’Connor’s death in 1924. St. Paul gangsters knew when they had a good thing going. Anyone caught violating the rules or breaking their pledge not to commit a crime was dealt with quickly and severely. According to St. Paul historian Paul Maccabee, St. Paul was a very safe place to be. Not just for criminals, but also for citizens and police. Safety aside, many of St. Paul’s residents resisted Prohibition and being treated like criminals for buying a beer. They were happy to flout, even help violate, a rule with which they didn’t agree. But the system broke down once criminals became bold. They were committing crimes within the city, ignoring the terms of the O’Connor agreement. The glory years were over, gone out with a literal bang, one as loud as the car bomb that killed Dapper Dan Hogan.

Where Do We Find This Stuff? Here Are Our Sources:

A shootout at St. Paul’s Lincoln Court Apartments. Ron Dansley,, 14 July 2021.

Crooks’ haven: The gangster era in St. Paul. Sharon Park, MinnPost, 10 November 2015.

Gangster era in St. Paul, 1900-1936. Sharon Park, MNopedia, 4 November 2015.

John Dillinger Slept Here. Paul Maccabee (1995). Minnesota Historical Society Press.

O’Connor Layover Agreement. Matt Reicher, MNopedia, 14 July 2014.

That time John Dillinger shot his way out of a St. Paul apartment building. Nick Woltman, St. Paul Pioneer Press, 31 March 2016.

The O’Connor Layover System. Edward J. Steenberg, Saint Paul Police Historical Society, (n.d.).

Next chief of police: John J. O’Connor, whose reputation as a thief-catcher is national. (n.a.) The St. Paul Globe, 3 June 1900.

Lincoln Court Apartments. HTC, Historic Twin Cities, 5 December 2019.

The Volstead Act. Kerry C. Kelly, National Archives, 24 February 2017.

St. Paul’s Nina Clifford: the richest woman of the underworld. Alexandra Scholten, MNopedia.