Tommy O’Connor was born in Limerick, Ireland in 1889, the O’Connor family emigrated from Ireland and settled in Chicago. He didn’t come to police attention until 1921.
Police had been trying to find Tommy O’Connor as he was the suspect in another crime. Police surrounded a building on Washtenaw Avenue. O’Connor fled out the back door and a shootout happened between O’Connor and the police, one officer Patrick O’Neill was shot and died. Police arrested O’Connor’s sister and brother-in-law but O’Connor fled Chicago and ended up in St. Paul, Minnesota.
Interestingly, St. Paul in Minnesota was known as a safe harbor for many criminals such as the Barker Gang, John Dillinger and Babyface Nelson to name a few.
O’Connor was sent back to Chicago where he stood trial, was found guilty, and was sentenced to hang. However, a few days before his trip to the gallows, O’Connor and four other prisoners overpowered the guards, stealing one of their rifles and escaping.
Three of the escaping prisoners were caught and returned to the courthouse, while Tommy O’Connor was last seen running through the traffic and that was the last time he was seen in Chicago or anywhere.
O’Connor was never caught but police believed he was involved in a robbery in Detroit, that ended in another shootout with police where an officer and two of the robbers were killed, O’Connor was not one of them.
Police believed that Tommy O’Connor died sometime in 1951. At the time of his death, he was still scheduled to hang. In 1977, when the gallows were removed in Cook County, Illinois, O’Connor was still scheduled to hang.