The dignified old building hulking over Hubbard Street at Dearborn was once the Cook County Criminal Court. It also contained the county jail, and that's the setting for our story.
Tommy O'Connor was a young punk who specialized in armed robbery in the Maxwell Street area. In the spring of 1921 he killed a policeman who was trying to arrest him. O'Connor was caught, found guilty of murder, and sentenced to hang. The execution was set for December 15.
O'Connor was housed in the jail's fourth-floor cell block. Things were quiet there on Sunday, December 11. At 9:30 that morning the cells were open, and the prisoners were taking their exercise in the common area. A single guard was on duty.
Suddenly, O'Connor produced a gun. He took the guard's keys, bound and gagged the man, and locked him in a cell. Then O'Connor opened the gate to the cell block. With four other prisoners, he walked out.
On the third floor O'Connor's group subdued three more guards. Next they took a freight elevator to the basement, where they overpowered a fifth guard, as well as five trusties. The escapees then ran across the open-air yard, climbed over a shed, and dropped down into the alley behind the building.
By this time the alarm had been sounded. Two guards rushed outside just in time to see O'Connor jump on the running board of a passing car, and force the driver at gunpoint to speed away.
Two of O'Connor's companions were immediately recaptured. The other two were caught later. Tommy O'Connor was never seen again.
Rumors persisted that O'Connor's escape had been an inside job, but nothing was ever proven. In later years O'Connor-sightings were reported at various places around town. The legend of Terrible Tommy grew. One story said he had gone to Ireland to fight for the IRA. Another claimed he had repented his wicked ways and become a Trappist monk.
Now for a footnote on the nature of the bureaucratic mind.
Tommy O'Connor had been sentenced to be "hanged by the neck until dead." A few years later, when the state abandoned hanging in favor of the electric chair, some nitwit decided that the gallows had to be saved, in case O'Connor were ever recaptured.
So the gallows was taken apart and stored. When the new county jail opened, it was moved there. In 1977, officials concluded that they weren't likely to run into O'Connor again, and the macabre keepsake was finally sold.