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

Gangsters helped two young, entrepreneurial boys run a lucrative, but extraordinarily dangerous business in the chill of St. Paul, Minnesota during Prohibition, the federal ban on manufacturing and sale of alcohol. The boys knew “a guy” running an illegal bar and transported liquor for him. They didn’t know where the liquor came from and didn’t ask. Before the liquor made it to its destination, the boys siphoned some, replaced it with tap water, collected the stolen liquor, and sold it on the side. One of the boys, telling his grandchildren (one who grew up to write for a certain history site) about this decades later recalled with hushed tones, “If we had been caught, we would have been put in the lake.” Covert alcohol operations happened freely in St. Paul. The city was under the O’Connor system, where Prohibition-era gangsters were free to operate, so long as they kept their crimes outside of St. Paul.

This Random City Was A Literal Paradise For Prohibition Gangsters
St. Paul Police Chief John O’Connor, author of the O’Connor system (1912). MN Historical Society. Public domain.

Police Chief John J. O’Connor – Cleaning up St. Paul’s Streets

St. Paul lies along the Mississippi River making it a perfect rail and river transportation hub, shipping goods to and from major markets like Chicago to New Orleans. It was a bustling city of over 160,000 people in the early 1900s, with its share of criminal activity. John J. O’Connor was named St. Paul’s Chief of Police in 1900. A headline touted him as “Desirable change for the city.” He upheld his duty to reduce crime and make St. Paul safe- and did his job well. O’Connor was hailed for significantly reducing crime in St. Paul during his tenure. Despite his reputation as a solid, upstanding law enforcement officer, O’Connor’s method of crime prevention was unorthodox. When O’Connor took office, he discreetly passed the word around the criminal world that St. Paul would offer them safe haven, as long as they didn’t commit any crimes within St. Paul itself.

This Random City Was A Literal Paradise For Prohibition Gangsters
Sheet music from temperance song, M. Evans, M. Gray, 1874. Public domain.

The Temperance Movement Grows

While O’Connor was cleaning the streets of St. Paul, the nation was battling over alcohol. The temperance movement had been brewing in the United States since the 1820s, formally organizing in 1826 as the American Temperance Union. Members saw alcohol as the driving force behind the erosion of public morals and damage to families. The movement wanted the government to impose controls on alcohol. Their efforts resulted in local laws imposing restrictions on alcohol production and sale. Many counties and states passed prohibition regulations between 1905 and 1917. Some of these regulations are still in place; Lynchburg, Tennessee is still a “dry” county. Ironically, it is also home to the Jack Daniels distillery, one of the most prolific whiskey makers in the world. But the nation would be rocked with the passing of the 18th Amendment officially enacting Prohibition across the United States.

This Random City Was A Literal Paradise For Prohibition Gangsters
Andrew Volstead (c. 1933). Minnesota Historical Society.

Gangsters thrive under the Volstead Act of 1919

Following the passage of the 18th Amendment, the federal ban on production and sale of alcohol, government passed enforcement legislation. The National Prohibition Act of 1919, called the Volstead Act for the chair of the House Judiciary Committee, Minnesota representative Andrew Volstead, defined the process and procedures government could use to enforce Prohibition. President Woodrow Wilson vetoed the Volstead Act, but Congress voted to override Wilson’s veto. Breweries officially shut down their alcohol divisions – at least on paper, although there were plenty of breweries covertly producing beverages. Bars and restaurants quickly sold off their liquor supply and went “dry.” Distributors had to find another market. Partying moved underground to speakeasies and hidden clubs. People who were normally law-abiding became criminals by buying a case of beer or making it in their homes. A new avenue of revenue opened up for the criminal realm. And St. Paul welcomed them all.

This Random City Was A Literal Paradise For Prohibition Gangsters
St. Paul skyline on vintage postcard. Joe Haupt, CC BY-SA 2.0.

O’Connor Opens St. Paul

O’Connor’s method of keeping St. Paul safe resulted in an unwritten policy, now referred to as the O’Connor Layover Agreement, in 1900. The goal was to keep crime out of St. Paul by turning the city into a sanctuary for gangsters. The police ignored their smuggling, gambling, (later) alcohol production and distribution, and other offenses, at least the ones kept underground and discreet. Police quietly protected the criminals while they were within St. Paul, letting them know about federal raids before they happened. As long as the gangsters behaved themselves within St. Paul’s borders, they were welcome to do as they pleased in other districts. St. Paul wouldn’t even extradite them to these other jurisdictions if they got caught. It kept crime down within O’Connor’s realm, the other cities, even St. Paul’s twin city of Minneapolis, be damned. They could deal with their own crime.

This Random City Was A Literal Paradise For Prohibition Gangsters
Labor unions protest Prohibition (c. 1920s). Public domain.

Gangsters Meet St. Paul’s Thirst

Prohibition wasn’t universally embraced. O’Connor and other police officials found it was hard to enforce laws that so many of the population refused to accept. People wanting a drink either had to find a black market supplier or make it themselves, creating their own moonshine in unregulated stills. But it was easier to find a “supplier” who would be able to provide it, and the gangsters of the era were happy to oblige. The O’Connor system attracted these bootleggers to St. Paul. The market still existed, since alcohol was unwillingly whisked out of consumer hands, and gangsters could fill the void. According to St. Paul historian Paul Maccabee, everyone, from the criminals to the police, to the law-abiding citizens, knew the police were turning a blind eye. The city was “dry” according to the federal government, but under the surface, it was very ‘wet.’

This Random City Was A Literal Paradise For Prohibition Gangsters
Fifth Street From St. Peter, Published By Wright, Barrett & Stilwell Company. Joe Haupt, CC-BY-SA 2.0.

Gangsters had Rules, Though

Gangsters seeking safe haven in St. Paul were bound by three firmly enforced rules. First, when they came to town they had to “check in.” Second, they had to pay a portion of any income (including illicit income) to the police department. Third, they were free to come and go as they pleased, but they were not to commit a crime in St. Paul. They could go to other cities to do their deeds. These rules were strictly enforced. As author and St. Paul historian Paul Maccabee says, “If you were caught snatching jewelry from around the neck of a woman on the streets of St. Paul, the police didn’t arrest you but took you up to O’Connor’s office where they beat the crap out of you and you limped out. And you thought twice about snatching a necklace in St. Paul.”

This Random City Was A Literal Paradise For Prohibition Gangsters

A Who’s Who of Prohibition Gangsters

The O’Connor system made St. Paul an attractive destination for mobsters to lay low, recover from injuries, or plan their next ‘project’ undisturbed by local authorities. The roster of mobsters who called St. Paul their home periodically during the O’Connor system years is a real Greatest Hits of the underworld:

This Random City Was A Literal Paradise For Prohibition Gangsters
St. Paul Union Depot, where O’Connor’s men scanned the crowd. Schwerdf (2012, CC 3.0).

A Well-Organized Operation

St. Paul’s Union Depot was constantly bustling with people coming to St. Paul. Happy people greeting loved ones, sad people seeing someone board their train for distant destinations. Among these throngs of people coming through Union Depot were gang members from Boston, New York, Chicago, all of the other criminal hotspots around the country. One of O’Connor’s men, trained to recognize specific criminals or to look for potential signs of underworld connections (an early form of profiling) waited at the inbound train platforms. If he identified someone of interest, he would discreetly go up to them and tell them if they planned to stay in St. Paul, they needed to go see a specific person at a specific place. This new arrival was an underworld luminary who was close to the police and could transfer the bribe to the appropriate officials.

This Random City Was A Literal Paradise For Prohibition Gangsters
Dapper Dan Hogan. Historic Twin Cities, posted 15 January 2020.

Gangsters go-between “Dapper Dan” Hogan

From 1913 to 1928 inbound criminals were usually directed to visit “Dapper Dan” Hogan to pay their bribe. This boisterous Irish gangster was the boss of the St. Paul criminal underground for most of the 1920s. As the new arrivals to St. Paul’s underworld presented their bribes to Hogan, they pledged to adhere to the ‘rules’ of the O’Connor system without fail. Once they took the pledge, they were under Hogan and St. Paul’s protection. If the FBI or other federal agencies came looking for someone, police notified Hogan, and Hogan tipped off the criminal. They weren’t just safe from criminal prosecution in St. Paul; as long as they adhered to the pledge, St. Paul officials would refuse to extradite them to other jurisdictions. Hogan served as a liaison between St. Paul police and the gangsters holed up in the city until his car bomb death in 1928.

This Random City Was A Literal Paradise For Prohibition Gangsters
Jack Pfeifer (c. 1936). MN Historical Society.

Peifer Finds Homes for Wandering Underworld

When gangsters finished paying their due to go-betweens like Dapper Dan Hogan, they needed a place to live. Since apartment search web sites were eighty years away, and many gangsters were unfamiliar with St. Paul’s real estate market, they relied on help from ‘fixers.’ One of the best fixers was Jack Peifer, owner of the Hollyhocks Club, a popular hangout for gangsters and ‘legit’ citizens alike. Peifer would set up newly-arrived gangster in a favorite apartment, often the Cle-Mar apartments on Cleveland and Marshall Avenues. These gangster homes were quickly set up with a telephone. The phone was a lifeline between the criminals and go-betweens like Hogan and underworld fixer Harry Sawyer. When police planned a raid on a gangster’s residence, they would be tipped off by a ‘friendly voice’ via phone, and usually had enough time to grab their belongings (and any evidence) and flee the scene.

This Random City Was A Literal Paradise For Prohibition Gangsters
Alvin Karpis (1925). Minnesota Historical Society, public domain.

The Barker-Karpis gang comes to St. Paul

An infamous gang came to St Paul in the early 1930s; Barker-Karpis gang. Alvin Karpis met Fred Barker in 1931 as inmates at Kansas State Penitentiary. After being released in 1931, Karpis met up with Fred Barker, his brother Arthur “Doc” Barker, and their mother Kate (known as ‘Ma’), forming the core of the Barker-Karpis gang. Karpis insisted that despite her reputation, Ma Barker knew about but wasn’t involved in any of the gang’s criminal activities. After a Missouri crime spree, fixer Harry Sawyer helped the Barker-Karpis gang (and their Ma) find a home in St. Paul. They lived in the relative safety of the O’Connor system while committing crimes across Minnesota and the Midwest. But it wouldn’t take long for someone to recognize the gang; after all, a popular magazine featured them in a true crime profile.

This Random City Was A Literal Paradise For Prohibition Gangsters
Fred Barker of the Barker-Karpis gang (1930). Public Domain.

The Gordons of Cle-Mar

The Barker-Karpis gang had to leave their first St. Paul residence when the landlord’s son recognized them from their profile in True Detective magazine and called police. Thanks to the O’Connor system, police tipped the gang off to a raid, giving them time to flee. The gang settled at the Cle-Mar as “The Gordons.” When the FBI raided that residence, the building’s janitor reported that they would be away for several-week stretches. And when the FBI inspected their apartment, it had numerous chauffer’s caps inside. Historian Paul Maccabee says the caps were popular with criminals, used as a disguise. The caps gave them a reason to be sitting in a car outside a bank or a residence for extended periods of time. The Barker Gang, minus some of their cap collection, soon moved on to an apartment about two miles away, at 1290 Grand Avenue (today the Grand Heritage apartments).

This Random City Was A Literal Paradise For Prohibition Gangsters
Vintage phone, a vital link in the St. Paul underworld. George Hodan (n.d., CC 1.0)

Gangsters Phone Lines Required

When the Barker-Karpis gang moved to Grand Avenue in 1933, they rented three apartments to accommodate their associates. Their brood included swindler Earl Christman, and Jess Doyle, a gunman involved in about half of the gang’s bank heists, and others returning to Minnesota after fleeing the frigid Minnesota winter in warmer climates. But the Barker-Karpis gang forgot one important thing. The telephone Harry Sawyer insisted upon to tip them off about police or FBI raids. The Barker-Karpis gang hadn’t been at 1290 for a month and had yet to set up this vital service. Unfortunately for them, on March 4, Harry Sawyer got a tip from a contact at the police department about an impending raid. Police still conducted raids to keep up appearances for the feds. Not having a phone could have had deadly consequences, had it been anywhere except St. Paul.

This Random City Was A Literal Paradise For Prohibition Gangsters
Jess Doyle, Barker-Karpis associate. Photo found by Jay Downs, posted on Antiquers com, 2021.

Gangsters Alerted to Raids

The Barker-Karpis gang’s lack of a phone meant Harry Sawyer had to send his wife Gladys to alert the gang about the police raid. While Gladys was inside the building warning the Barkers and Karpis, another gang member arrived. The gang’s associate, robber Jess Doyle, arrived at 1290 that evening, spotting the police officers as he sauntered nonchalantly by the officers waiting to begin the raid. Doyle casually packed his suitcases and walked right out the front door past the police. The police, knowing Gladys Sawyer was in the apartment warning the gang, indifferently waited until everyone evacuated to start the raid. The public saw police “cracking down” on crime by raiding 1290. The St. Paul police kept their word and avoided actually doing anything, even with criminals nearly in hand. And the FBI saw St. Paul being tough on crime.

This Random City Was A Literal Paradise For Prohibition Gangsters
Jack Peifer. Minnesota Bureau of Criminal Apprehension (BCA).

Peifer Taps Barker-Karpis for the Big Score

In April 1933, Jack Peifer invited the Barker-Karpis gang to the Hollyhocks club to propose a job. He wanted the gang to kidnap the president of Hamm’s Brewing Company, William Hamm Jr., whom he met at his Hollyhocks club in 1931. Hamm was president of one of only six St. Paul breweries out of the city’s original sixty to survive Prohibition. Hamm’s Brewery successfully back in business when the Cullen-Harrison Act was passed in March of 1933, a step toward officially repealing Prohibition. The Hamms were making money again. Peifer wanted a ransom of $100,000 for the kidnapping. This seems like a small amount for such a high-profile kidnapping, but according to historian Paul Maccabee, the kidnaping was more politically motivated than financial. The gang and their associates retreated to their Idlewild resort to plan the job.

This Random City Was A Literal Paradise For Prohibition Gangsters
Kate “Ma” Barker. Biography

Being good neighbors while planning a notorious kidnapping

Idlewild was a resort community just north of St. Paul where the wealthy would vacation with their families, spending their days at leisure, yachting, swimming, playing tennis. F. Scott Fitzgerald and his wife Zelda were Idlewild visitors. Jack Peifer, who set up the Barker-Karpis crew with cabins as they planned their kidnapping. The Idlewild community embraced Ma, Fed, Doc, and Alvin as a quiet family of entertainers who bought raffle tickets from their kids and held ice cream socials for the neighborhood. Ma would pay kids quite well to mow the lawn. One day the gang was target shooting, and a neighbor came by to scold them, “You cut this out! There are kids around here!” and they stopped, even looking a little ashamed. All the while, the gang were plotting what would be one of St. Paul’s most notorious crimes.

This Random City Was A Literal Paradise For Prohibition Gangsters
Hamm Brewery, with Hamm mansion to the right, in background. Minnesota Historical Society

Hamm Kidnapping was a Success

To prepare for the Hamm kidnapping, the group observed Hamm so long Alvin Karpis says, “We got to know so much about the guy that I was sick of him long before the kidnapping.” Each day, Hamm would walk from the brewery to his nearby mansion for lunch. On June 15, 1933, Karpis sat in an idling car wearing a chauffer’s cap so Hamm wouldn’t be suspicious. At 12:45 pm, Hamm strolled to his mansion for lunch. The “greeter,” Charlie Fitzgerald had a dignified look to him that raised no alarm. He walked up to Hamm, extending his hand for a handshake. Gripping Hamm’s elbow with his other hand, Fitzgerald asked, “You are Mr. Hamm, are you not?” Hamm affirmed his identify. Fitzgerald tightened his grip, Karpis moved the car forward, and an associate blocked Hamm. They put a pillowcase over his head and moved Hamm into the vehicle.

This Random City Was A Literal Paradise For Prohibition Gangsters
W.W. Dunn (l) and William Hamm, Jr. (r) (1933). Minnesota Historical Society.

En Route to the Hideout

The gang had prepared well; license plates switched, and gas cans stowed to avoid a gas stop along the way. They lined up a contact at the Saint Paul Police Department who warned the group about any traces of evidence being investigated. The group would have ample warning of a raid and know where the police were in their investigation. When they were about thirty miles out of St. Paul, the group met up with other conspirators. The group split up; some conveying Hamm to Bensonville, Illinois, the others returned to St. Paul to negotiate the ransom. Hamm was asked who might best serve as a trustworthy contact. He identified the Hamm’s brewery’s sales manager William W. Dunn. The gang was particularly pleased with this choice since Dunn was known to keep quiet when he needed to and had ties to the St. Paul Police Department.

This Random City Was A Literal Paradise For Prohibition Gangsters
The Bensonville house where William Hamm was taken during kidnapping. Minneapolis Tribune, April 19, 1936.

A Quick Resolution

En route to Bensonville, the group had Hamm sign ransom notes, then sent them to William Dunn. Dunn arranged the ransom payment for drop at a location north of St Paul. The ransom payment had to be delivered by a car with doors removed (to prove there weren’t extra people inside) and displaying a red light. They didn’t know the FBI developed latent fingerprint identification for the first time, but had not yet identified them. With the ransom paid (and ransom notes on their way to the FBI), Hamm was taken from captivity to a spot about fifty miles north of St. Paul and dropped off safely. As the FBI investigated the kidnapping, the group was tipped off by Jack Peifer to a raid at their money-laundering location. They fled their hideout with time enough to remove all evidence of their crime. The Hamm kidnapping was over in three days.

This Random City Was A Literal Paradise For Prohibition Gangsters
Harry Sawyer. Minnesota Bureau of Criminal Apprehension (1935).

Barker-Karpis Strike Again: The Bremer Kidnapping

In December 1933, the Barker-Karpis gang accepted another kidnapping job. This time, at the suggestion of fixer Harry Sawyer, they would target bank president and heir to the Schmidt Brewing fortune Edward Bremer for a ransom of $200,000. Unlike Hamm, Bremer was less a political kidnapping and more personal. Karpis said, “I don’t know what Sawyer’s beef was, but he sure didn’t like Bremer.” (Maccabee, pg. 187). There were disagreements over alcohol, but even Bremer, who worked with FBI agents to solve his kidnapping, wouldn’t reveal what these were. But the Bremer kidnapping wouldn’t be as smooth as the Hamm job. Karpis felt the plan was a bad move right off the bat, but went along with it anyway (hindsight proves his instincts correct; he was brought to court for Hamm and Bremer kidnapping charges. He pled guilty). The gang and their associates were arguing just days before it happened.

This Random City Was A Literal Paradise For Prohibition Gangsters
Edward Bremer (1934). Minnesota Historical Society.

Gangsters vs. Bremer

As Bremer dropped his daughter off at school on January 17, 1934, the group “greeted” him and hustled him into a car, much as they did during the Hamm kidnapping. This time, however, the greeting was less cordial. Blocking Bremer’s car with theirs, a gang member put a gun to his stomach, threatening to kill him if he moved. Bremer put up a fight, trying to block the car door from closing. The gang member hit him over the head with the gun, drawing blood and slammed the door so hard it injured Bremer’s knees as he tried to keep the door open. Bremer decided to comply when it became clear that the beatings would continue if he did not. A call to Bremer’s friend set up the ransom demand.

This Random City Was A Literal Paradise For Prohibition Gangsters
President Franklin Delano Roosevelt, personal friend of the Bremer family. Public domain (1932).

Gangsters Ran into Trouble

Unfortunately for the gang, the FBI was on high alert in St. Paul after the Hamm kidnapping. And the Bremer family was friends with President Franklin Delano Roosevelt. The FBI wanted to resolve this kidnapping and ensure there would be no more. This kidnapping was a more difficult experience for the gang than the Hamm job. There was a great deal of blood in the car. The FBI tapped the Bremer phones. The family claimed they were “cash poor,” and offered half the ransom. Hamm’s family paid their ransom within a couple days. Bremer’s was dragging for weeks. Where Hamm had been reasonably pleasant to kidnap, the injured Bremer was proving to be more vocal about his injuries and his grievances with his situation. Despite the FBI’s resolve to capture the kidnappers, Bremer’s family refused to cooperate with them, preferring to deal with the kidnappers directly.

This Random City Was A Literal Paradise For Prohibition Gangsters
An FBI fingerprint kit from the 1930s. Federal Bureau of Investigation (2016, public domain).

Bremer Gangsters Revealed by Fingerprint Technology

After three weeks, the family put together the $200,000 for the ransom. Bremer was released near Rochester, Minnesota, injured but alive. But it was a close call; the negotiation dragged on so long Karpis worried they might have to “do something he didn’t want to do” to take care of the problem. The FBI caught a break in the Bremer case, however, when a farmer in Wisconsin found gas cans in his field. The cans had Doc Barker’s fingerprints on them. Within two years, the fingerprints helped the FBI identify the Barker-Karpis gang and their associates as the kidnappers. Despite the gang moving away from St. Paul in the wake of the Bremer kidnapping and their efforts to hide, theFBI captured them. Everyone involved was jailed or killed. But the Hamm and Bremer kidnappings put a deep crack in the O’Connor system, one from which it never recovered.

This Random City Was A Literal Paradise For Prohibition Gangsters
St. Paul Police Chief Thomas A. Brown. Public domain.

Gangsters find their Safe Haven Breaking

The Hamm and Bremer kidnappings ended with the safe return of the victim. The official line was that the kidnappings were shocking because the underworld had intruded on the “overworld,” the criminals picked non-criminal targets. This isn’t quite right, according to historian Paul Maccabee. He claims the two worlds blended for years. St. Paul citizens were perfectly content – even excited – about their scandalous neighbors. The biggest concern centered around the crimes happening in St. Paul. The O’Connor system was clear – St. Paul was off limits. These crimes violated the oath. Additionally, the FBI identified Police Chief Thomas A. Brown, a chief supported by the underworld, as the source of leaks that allowed the Barker-Karpis gang to get away before the FBI could raid their compounds. The St. Paul Police Department fired Brown, but the crooked chief never faced charges.

This Random City Was A Literal Paradise For Prohibition Gangsters
John Dillinger, 1924. Public domain.

A Famous Gangster’s Face and a Notorious Place

Despite the crack in the oath, FBI’s Public Enemy Number One, John Dillinger, called St. Paul his home in March 1934. He had recently broken out of jail in Indiana, robbed an Iowa bank resulting in a gunshot wound. Dillinger came to the Twin Cities to recover, preparing for the next round of robberies. He and girlfriend Evelyn Frechette, under the pseudonym Hellman, rented an apartment in the Grand Avenue area, the Lincoln Court Apartments. The couple took great pains to be discreet. They only used the back door. They refused to let anyone aside from their associates into the apartment. But this discretion actually caught the attention of the couple’s landlord, Daisy Coffey. When the couple refused to let a maintenance worker into the apartment for maintenance, her suspicions flared. She contacted the FBI about the couple, who sent St. Paul Police officers to observe the building.

This Random City Was A Literal Paradise For Prohibition Gangsters
John Dillinger’s girlfriend Evelyn Frechette (1934). MN HIstorical Society, public domain.

The Quiet Couple Gets Loud

The police watched the Lincoln Court Apartments for suspicious activity all night. In the morning, FBI agents R. C. Coulter and Rosser Nails, with St. Paul police officer Henry Cummings approached unit 303, where the low-key couple resided, and knocked on the door. The woman, Dillinger’s girlfriend Evelyn Frechette, asked the officers for a minute so she could dress before speaking with them. As they waited, Dillinger gang associate Homer Van Meter sauntered toward the apartment. Cummings and Coulter requested identification from the young man. Van Meter claimed he was a soap salesman and walked with Coulter to the first floor of the building. Instead of handing over his wallet, Van Meter pulled out a pistol. Coulter fled the building, Nails following, exchanging gunfire with Van Meter. Van Meter encountered a garbage collector, stole the collector’s horse and hat, and fled the scene.

This Random City Was A Literal Paradise For Prohibition Gangsters
A Thompson submachine gun, 1928 model. National Park Service (NPS), 2005, CC 3.0 .

A Painful Escape

While Coulter and Nails were battling it out with Van Meter, Dillinger opened his door just wide enough to stick the barrel of his Thompson submachine gun into the hallway and spray it with bullets. Cummings took cover around a corner, returning fire. A shot hit Dillinger, who was already recovering from a bullet wound, in the leg. The wounded Dillinger and Frechette, taking advantage of the melee, escaped down the back stairs. Frechette retrieved a car while Dillinger continued the gunfight. He hopped in, and they drove to the clinic of Dr. Clayton May in Minneapolis. Dillinger and Frechette stayed four days while his leg healed. They left for upper Michigan, where they would lay low until their next exposure at the Little Bohemia Lodge in Rhinelander, Wisconsin, scene of an infamous shootout with FBI agents.

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.