The twisted tale of Terrible Tommy O’Connor

Chicago Police mugshots of Limerick man Tommy O'Connor.

THOMAS O’Connor was born in Limerick in 1880 but history would know him as Terrible Tommy – the last man sentenced to hang in Chicago.

Terrible Tommy was the son of Joseph O’Connor and Elizabeth Roach of Ballykenny near the village of Strand. Before his third birthday, young Tommy emigrated with his parents and siblings to America where the family settled in the rough Chicago neighbourhood of Bloody Maxwell.

Tommy’s brother John became an electrician and his sister Mary also led a crime-free life. His other brother David became a successful broker but he caused controversy when a messy divorce resulted in his arrest for ‘immoral conduct’ and local newspapers in the Windy City dubbed him ‘Darlin’ Dave’ as his wife claimed he had carried out a string of affairs with other women during their marriage.

Tommy chose a life of crime and ran with street gangs during his teenage years but he did not come to police attention until he was 21 following the murders of two men – a retired police officer and a criminal associate. The police accused the Limerick man of murdering them and shady court dealings resulted in his release but, Tommy’s freedom would not last long.

There have been many tales regarding how Tommy O’Connor became ‘Terrible’.

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His disloyal attitude which saw him betray and possibly kill associates may have earned him the moniker while another theory recalls how his fierce temper saw him chop the thumb off a butcher who overcharged his mother!

However, he gained his nickname, Tommy O’Connor’s criminal actions could indeed be described as terrible.

His route to criminal infamy began on a cold March morning in 1921 when five police men arrived at the home of his sister on south Washtenaw Avenue to arrest him on the murder charges he had previously slipped away from.

Chicago police detective Patrick O’Neill, a fellow Irishman, knocked on the door with a warrant for Tommy’s arrest but, what followed would result in the death of the Irish American cop.

Popular belief dictates that Terrible Tommy burst out the front door brandishing two guns and then sprayed the policemen with bullets. The less fantastic and more likely scene saw a brief gunfight break out between Tommy inside the house and the policemen who were on the porch.

When a bullet brought down Detective O’Neill, Tommy made his getaway out the back door, over a fence and into the street where he hijacked a car.

Detective O’Neill died from his wounds and the inquest that followed resulted in the suspension of the policemen who had accompanied O’Neill. The judge was not satisfied with their conflicting stories and poured scorn on their carelessness. The inquest found that the officers had fired indiscriminately and the judge declared it “the worst case of dog eat dog I have ever seen!’

Detective O’Neill left behind a widow and three young children and terrible Tommy made his get away to St Paul Minnesota.

In July 1921, Terrible Tommy was making a drunken nuisance of himself on a train in St. Paul. The police arrested him and when word filtered back to Chicago that their wanted man was sitting in the county jail in St Paul Minnesota, the Chicago Police Department dispatched a group of heavily armed detectives to bring him back.

At the time of his arrest in Minnesota, Terrible Tommy had just four items in his possession: rosary beads, a scapular, a St Patrick prayer card and a pistol!

He was brought back to Chicago where in September 1921 he was sentenced to hang. The date for the hanging was penciled in for December 15th but, four days before his execution, the condemned Limerick man escaped.

As prison guard David Strauss was walking past Tommy’s cell, he called the guard who then, rather unwittingly, approached the bars. Tommy’s cell mate James La Porte grabbed the guard in a head lock while Tommy grabbed the cell keys dangling from his belt. Tommy opened the door of his cell and took the guard’s gun while his cell mate bound and gagged him.

The two prisoners ran for the prison yard and along with four other prisoners they scaled a 20ft wall to freedom. Terrible Tommy hijacked a car but in the wintery weather it slid on ice and crashed into a store front.

Tommy managed to bundle himself out of the wreck and ran off down a side street. The Limerick-born Chicago hoodlum who was only days away from the gallows disappeared into thin air.

Even though the police launched a massive manhunt across America, they never found Terrible Tommy.

Sightings of him were reported in various towns and cities across the states. He was sighted in places such as Texas and Los Angeles and even across the border in Canada. It was even claimed that he made his way back to the land of his birth where he offered his services to the IRA.

Other rumours arose that he robbed banks on route to Canada before taking his loot on a ship bound for Limerick where he bought a public house under a fake name and lived out his days on Shannonside.

In 1937 it was suggested that Terrible Tommy had died form tuberculosis, a disease which had previously affected him in his childhood. Another rumour claims that his gravestone can be seen in the Holy Sepulchre Cemetery in Cook County Illinois where the date of death indicates January 31, 1951.

The gallows that had been built for Terrible Tommy’s hanging remained in place until 1977 when it was dismantled and sold to Ripley’s ‘Believe It or Not’ Museum. A sign had been painted on the structure “Tried of Waiting Tommy!”

Every year on the anniversary of Terrible Tommy’s escape from the gallows, the Chicago Tribune columnist Tom Powers would write a piece about the Limerick man which always began with the following: “Dear Terrible Tommy O’Connor, if you are still alive please contact me so I can quit writing these columns!”

Well, the search continues….

by Pauline Murphy