Terrible Tommy O’Connor: Chicago Gangster

Updated on September 6, 2019
Rupert Taylor profile image

I've spent half a century (yikes) writing for radio and print—mostly print. I hope to be still tapping the keys as I take my last breath.

Tommy O'Connor's mug shot. Sometimes looks are not deceiving.
Tommy O'Connor's mug shot. Sometimes looks are not deceiving. | Source

The scourge of Chicago in the 1920s was gangs and crime (some things never change). Among its denizens was an Irish immigrant named Tommy O’Connor who earned a reputation as a violent thug. He became the subject of the most extensive, and unsuccessful, manhunt in the history of Illinois.

Early Days in America

Tommy O’Connor was born in Limerick, Ireland, in 1890 and was only two years old when he arrived in America with his family. They settled in a neighbourhood of Chicago whose nickname, Bloody Maxwell, tells you a lot about how desirable it was. Its other title of “the Wickedest Police District in the World” was descriptive of the gang violence that plagued the area and the unsavoury behaviour of the cops.

Tommy’s siblings largely avoided being contaminated by the crime that surrounded them. Brother John became an electrician and sister Mary settled down to a life without larceny. Older brother David, a broker, messed around with women not his wife but, as far as is known, did not steal or kill people; that was left to Tommy.

Tommy O’Connor’s Life of Crime

Tommy O’Connor flew under the police radar for several years. He was up to no good in those early years, he just never got caught. He and a fellow partner in crime, Jimmy Cherin, hung around a saloon operated by Jimmy’s father, Dominick. The bar was a place where stolen goods could be fenced and was the favourite watering hole for some of Chicago’s criminals.

It was here that Tommy and Jimmy learned how to steal cars and engage in other crimes. Tommy was known to have an explosive temper. On one occasion he believed his mother was overcharged for some meat so he chopped off the butcher’s thumb. Tommy soon developed a reputation as a “cold-blooded killer,” and acquired the moniker “terrible.”

Murder on Washtenaw Avenue

O’Connor was arrested for murder in 1921. Numerous accounts then refer to unspecified “shady court dealings” that saw O’Connor released. Chicago in the 1920s was a notoriously corrupt city (again, some things never change). Cops, judges, and politicians were on the take, so the notion of an accused murderer dodging justice was an unremarkable occurrence.

William Hale Thompson (above) was Chicago’s mayor from 1915 to 1931 with a break of four years in the middle. “Big Bill,” as he was known, was in a tight alliance with Al Capone and has been described as one of America’s most corrupt mayors.
William Hale Thompson (above) was Chicago’s mayor from 1915 to 1931 with a break of four years in the middle. “Big Bill,” as he was known, was in a tight alliance with Al Capone and has been described as one of America’s most corrupt mayors. | Source

But O’Connor’s freedom was short-lived. Somebody thought justice had been perverted and dispatched detective Patrick O’Neill to arrest O’Connor at his sister’s Washtenaw Avenue home. There was an exchange of gunfire, Officer O’Neill was hit and later died of his wounds.

O’Connor escaped out of the back of the house but was later arrested in St. Paul, Minnesota after making a drunken nuisance of himself. He was hauled back to Chicago, tried and found guilty of killing the police officer. The sentence was death by hanging to be carried out in the middle of December 1921.

Tommy O’Connor Cheats the Hangman

Four days before his date with the executioner, a prison guard was walking past O’Connor’s cell when the inmate called him over. O’Connor’s cellmate reached through the bars and put a head lock on the guard, while Tommy took his keys and gun. They bound and gagged the guard, ran into the prison yard, and climbed over a 20-foot wall.

Another version of the breakout is that O’Connor got a gun that was smuggled into the prison hidden in a sandwich. (Which leaves the writer puzzling over how to conceal a Colt 45 between two slices of whole wheat and a side of dill pickle). This version has O’Connor and four or five other prisoners overpowering several guards before escaping.

Whatever the correct story, this is when the legendary Chicago lawyer Harry J. Busch met Terrible Tommy O’Connor. At the time a law school student, Busch was driving his car in the neighbourhood of the Cook County Jail. More than 70 years later, Busch recalled what happened after a man jumped onto the running board of his car, “Suddenly the isinglass is ripped open, and in comes Tommy with his cannon. He said, ‘Drive like hell, you SOB, or I’ll blow your brains out! I’m Tommy O’Connor!’ I drove!”

Busch deliberately crashed his car into a factory wall. O’Connor scrambled out of the wreckage and was last seen legging it down the street. And, that was literally the last time he was seen.


A $3,000 reward (that’s more than $40,000 in today’s money) was offered for information leading to O’Connor’s arrest, but it was not enough to shake loose any tips. Hundreds of police searched for the fugitive, but he was never found.

Stories appeared frequently about sightings. He was in California, no it was Texas. He had joined the Irish Republican Army and been killed in a shoot out, no he’d died of tuberculosis. He was robbing banks in Canada, no he had bought a pub in Limerick.

There is a tombstone in Worth, Illinois, a suburb of Chicago, with the name Tommy O’Connor on it. The date of death is given as 1951.

The Cook County Gallows

In 1929, Cook County dropped the use of hanging in favour of electrocution for dealing with capital offences. However, the gallows was kept because O’Connor had been sentenced to death by hanging, so the equipment had to be ready in case he was captured. The hanging tree had originally been built to deal with those found guilty of the fatal bombing during the labour Haymarket Riot of 1886.

Four of the Haymarket conspirators face execution on the gallows Tommy O'Connor was supposed to be hanged on.
Four of the Haymarket conspirators face execution on the gallows Tommy O'Connor was supposed to be hanged on. | Source

It wasn’t until 1977 that a judge ordered the gallows dismantled and destroyed, by which time someone had attached a big sign to it reading “Tired of waiting Tommy.” But, an entrepreneur stepped in and bought it for display at Mike Donley’s Wild West Town in Union, Illinois. The gallows came up for sale again 2006 and was acquired at auction by Ripley’s Believe it or Not for $68,300.

Bonus Factoids

  • Tom Powers was a columnist with the Chicago Tribune who wrote a column about Tommy O’Connor every year on the anniversary of his escape. He started each article with a plea: “Dear Terrible Tommy O’Connor, if you are still alive please contact me so I can quit writing these columns. Call collect!”
  • The 75th anniversary of O’Connor’s escape occurred in 1996 and a reporter from the Chicago Tribune called up Harry Busch for a comment about his encounter with Tommy O’Connor. Busch, now well into his 90s responded by saying “My God. Will that piece of history never die?”
  • Ben Hecht and Charles MacArthur, both Chicago news men, wrote Terrible Tommy O’Connor into their 1928 play The Front Page. Their character Earl Williams was scheduled to be hanged for killing a police officer. The play centres on Williams’s escape from prison on the eve of his execution and his hiding out in the press room of the Chicago Criminal Courts Building. It was turned into a movie a couple of times, most recently in 1974.


  • “The Twisted Tale of Terrible Tommy O’Connor.” Limerick Post, August 11, 2018
  • “When Harry Met Tommy.” Michael Yockel, Chicago Reader, December 21, 2000.
  • “Chicago – America’s ‘Most Theatrically Corrupt’ City.” Toby Harnden, The Telegraph, December 12, 2008.
  • “Ripley’s Wins Bid for Historic Gallows.” Associated Press, December 8, 2006.

© 2019 Rupert Taylor


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