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
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.