The Great Escape (12-11-1921)

Tommy O’Connor was a young punk who specialized in armed robbery in the area around Maxwell Street.  In the spring of 1921 he killed a policeman who was trying to arrest him.  O’Connor was later caught, found guilty of murder, and sentenced to hang on December 15.

O’Connor was housed in the fourth-floor cell block of the old County Jail, just north of the Loop.  Things were quiet there on Sunday, December 11.  At 9:30 that morning the cells were open, and prisoners were taking their exercise in the common area of the cell block.  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 companions, he walked out.

“Chicago Tribune” diagram of O’Connor’s escape

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 jail.

By this time, the alarm had been sounded.  Two guards rushed out of the building just in time to see O’Connor jump on the running board of a passing car, and force the driver at gunpoint to get-the-hell-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 in 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.

IF YOU SEE THIS MAN, CONTACT POLICE!!!

Now for a footnote on the nature of 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 they weren’t likely to see O’Connor any time soon, and the macabre keepsake was finally sold.

—30—

2 Responses to “The Great Escape (12-11-1921)”


  1. 1 Garry December 11, 2019 at 10:19 am

    John, how could you leave out that Terrible Tommy’s escape was the basis of part of “The Front Page”?

    • 2 J.R. Schmidt December 11, 2019 at 12:18 pm

      I did mention that connection when I talked about the incident on the radio a few years ago, but I forgot to include it in this post. On a related matter, Ben Hecht also wrote one of his newspaper columns imagining what Tommy O’Connor must be thinking and doing as a fugitive. Called “The Man Hunt,” you can read that column in the Hecht anthology, A Thousand and One Afternoons in Chicago
      –JRS.


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