Tommy O'Connor was a bad man, a coldblooded killer who prowled Chicago as Prohibition descended. He was convicted of murdering one person — a police officer — and likely shot dead at least two more, including his best friend.
That's why they called him "Terrible" Tommy.
And O'Connor got away with it. One star witness was kidnapped days before a murder trial. Another escaped from prison before an armed robbery trial. O'Connor was acquitted of one homicide when three upstanding former soldiers testified he was with them in Texas. And when the long arm of the law finally did colllar him, try him, convict him and sentence him to hang, he escaped from the county jail with the help of a smuggled gun — and was never heard from again.
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6415 South Washtenaw Avenue, Chicago, IL 60629, USA
3399 West 60th Place, Chicago, IL 60629, USA
54 West Hubbard Street, Chicago, IL 60654, USA
Stickney, IL, USA
That's why they called him "Lucky" Tommy.
The audacious recent jailbreak from the Municipal Correctional Center in downtown Chicago triggered comparisons to O'Connor's own bold escape from the former county jail 91 years ago this month. Chicago has a long sordid history with crime, which it revels in even as it tries to keep its distance. Alfonso Capone is the most famous, of course, but nothing captures the public's imagination like the criminal on the lam, like John Dillinger, like "Terrible" Tommy O'Connor. Ben Hecht's hit 1928 play "The Front Page" and the 1931 and 1974 movies of the same name were loosely based on O'Connor's jailbreak.
But O'Connor's infamy started long before that final flight from justice. Indeed "Lucky" Tommy thumbed his nose at the law for years before he flew the coop for the last time. In a way, all of Tommy's troubles, self-inflicted though they were, began with the Feb. 1, 1918, armed robbery and murder of an Illinois Central railroad collector. One crime inexorably led to another.
O'Connor's first appearance in the Tribune appears to be in March 1918 when he's named as an accomplice in that crime. The murder of Dennis Tierney, an elderly former policeman, was first pinned on another man, who conveniently had been killed by police during the getaway. Later O'Connor was fingered as the triggerman, though never arrested.
The man doing the fingering, Harry Emerson, was in state prison at Menard. O'Connor figured that if he could silence him, his troubles would be over. He went to his best friend, Jimmie Cherin, who had run with Tommy on Maxwell Street in their youth and was known as the "Peacock of the Underworld." He had connections with the kind of people who could get someone killed behind bars.
Trouble was, Cherin was now a "square guy." He had a beautiful young wife and 3-year-old daughter. He wasn't in the racket anymore. O'Connor didn't want to hear that from his boyhood pal. Cherin's bullet-riddled body was found in the back seat of a car in Stickney in January 1919. Ten months later, O'Connor's fear came true; the law caught up to him. Where? The headline said it all: "Hunted 2 years as killer; found in home asleep."
But in April 1920, a jury acquitted O'Connor of killing Tierney after three former soldiers gave Tommy an alibi. However, instead of walking free, he was then held as chief suspect in the death of his friend Cherin — and there was an eyewitness. O'Connor and Cherin had been in the back seat. The car had been driven by Louis Miller, and he was willing to testify. They had O'Connor dead to rights.
But in September, two days before O'Connor's trial was to start, Miller was kidnapped from a Chicago restaurant. O'Connor walked. A few months later, Harry Emerson, slated to testify against O'Connor in still another trial, for armed robbery, somehow escaped while being taken back to Menard.
In January 1921, police arrested Miller in Rogers Park. He said gunmen had spirited him away to Madison and the West Coast before he had managed to get back home. Police immediately announced a manhunt for O'Connor.
It took them three months, but Chicago police finally found him — at his brother-in-law's house. A five-man squad went in for the arrest at 1 a.m. March 23. They surrounded the bungalow. One officer rang the bell. A moment later, O'Connor ran out the back and yelled, "You dirty ------, I'm going to get you anyway. You've hounded me long enough." He fired five shots, the last of which felled Detective Sgt. Patrick "Paddy" O'Neill, who was standing in the backyard. What happened next, as the Tribune reported the next day, was something of a mystery. O'Connor went back into the house. O'Neill languished, bleeding, in the backyard. The other officers regrouped in the front, leaving their fallen comrade alone. A number of minutes later, O'Connor ran out the back door, down the alley, hailed a cab and disappeared. O'Neill died; one witness said he wasn't helped for as long as 25 minutes. (The other officers eventually were fired for their incompetence.)
So began yet another manhunt for O'Connor. But police were at a loss.
A drunken O'Connor was arrested four months later two states away in St. Paul. On a train about to leave for Omaha, he stupidly threatened to kill a porter who had just served him a beer. Then he fled into the rail yard. He was captured easily by railroad workers. In a rare success, Chicago police dispatched a squad to get him, spiriting him out of Minnesota even as Minneapolis cops gave chase because O'Connor was wanted there for robbery.
On Sept. 24, 1921, O'Connor — still exclaiming his innocence — was convicted of killing O'Neill and sentenced to die. The execution date was set for Dec. 15, and as the day approached, the Tribune reported, rumors flew around town that "O'Connor would never hang" at the courthouse-jail complex bounded by Clark Street and Dearborn Parkway and Hubbard (then called Austin Street) and Illinois streets.
Of course, he didn't.
On Sunday, Dec. 11, O'Connor and five cellmates overpowered their incompetent guards using subterfuge and a smuggled nickel-plated revolver. O'Connor fought his way out of the prison, clearing a 20-foot wall. One prisoner broke both his ankles dropping to freedom on Illinois Street. O'Connor, though, commandeered a car, charging the frightened motorist to "drive like hell." They made it a block before the car stalled. O'Connor stole another. The manhunt that ensued yet again was bigger than anything Chicago had seen — since the last time O'Connor was on the run — and just as fruitless.
Police were inundated with tips. According to the Tribune, many purposely misled the cops, and not a few tips were intended as payback to settle grudges or harass innocents. Police raided one home three times. One anonymous citizen dropped a dime on a bishop he apparently didn't like. It didn't matter; the police raided the cleric's house — twice — desperate to erase the stain of O'Connor's embarrassing escape.
Just as the 2012 prison break revealed problems at the Loop facility, the Tribune reported how security at the county jail in 1921 was lax: Prisoners enjoyed a "moonshine jamboree" courtesy of a still in the basement, and guards fraternized with them. The jail chief was fired, and many of the guards involved in the escape were held as suspects. Numerous investigations were launched, but no conspiracy was uncovered.
In Chicago, O'Connor's ugly mug appeared again only in news stories on anniversaries of his escape. His longest-lasting gift to the city, other than his saga, was the gallows from which he never swung. The court ordered the county to keep the gallows until he was caught. Not until 1977 did presiding Criminal Court Judge Richard Fitzgerald reverse that ruling, giving up "hope that O'Connor ever would be captured."
By then, Tommy would have been 87. If still alive, he likely wasn't so terrible — but still plenty lucky.