Happy St. Patrick's Day from Terrible Tommy O'Connor

Happy St. Patrick's Day from Terrible Tommy O'Connor
Postcard from Tommy O'Connor

As my wife was placing the corned beef brisket into the crockpot and we were planning our St. Paddy’s Day activities for this evening, I went to the mailbox and found a postcard from an old Chicago buddy, Tommy O’Connor !

How cool to hear from him and know that he is doing well at the ripe old age of 135.

I had to write him a letter to fill him in on what has been going on here in Chicago since he left so abruptly on December 11, 1921.  Unfortunately he must have forgotten to put a return address on the postcard but I guess you can’t blame a guy for a little slip every now and then at his age.  So since I couldn’t put it in the mail I figured I would publish the letter online.


Hey Tommy,

Hope things are going well with you.  Things really haven’t changed much since you’ve been gone.  We have been through a number of sheriffs, police chiefs (we call them superintendents now), mayors and even jailed a few governors  since you’ve been gone.

I can’t say I approve of you shooting Chicago Police Sergeant Patrick O’Neill to death or the brutal slaying of your best friend Jimmy Cherin after he refused to kill your buddy Emerson for fingering you in a robbery.   I’m sure those were all frame-ups but I have always told you that you might benefit from some anger management classes or maybe even a yoga or pilates class or two.

Also wanted to apologize for the way Minnesota hung that “Terrible” nickname on you.  I thought your original names Lucky Tommy O’Connor or “Tommy The Immune” were much better.   Now we like to use the name “Teflon” instead of immune.

About six years after you left they stopped hanging people here and started using a device called the electric chair, nicknamed “Old Sparky”, to execute people.  It was a little tricky to learn how to use at first but eventually they got it right and then they stopped doing that here in 1962 and started using lethal injections.  I know, none of it sounds really attractive right?

The funny thing is that even after you left and they stopped hanging people the jail hung onto the gallows until 1977 because a judge ordered them preserved just in case you ever showed up again so that they could finish what they started.

After that they sold the gallows to a place called Donley’s Wild West Town in Union, IL.  It was displayed in an Old West styled village until 2006!  (Don’t tell me you never went there and took a selfie of yourself pretending to hang yourself as a gag!)

You wouldn’t believe that Ripley’s Believe it or Not bought them at auction from Donley’s in 2006 for $68,000!

Anyway, I thought for sure you would show up again after our ex-con governor George Ryan abolished the death penalty in Illinois in 2011 but I don’t blame you for being a little skiddish.  But seriously dude, you could make a ton of cash writing a book or starring in a reality television show so if you get a chance to read this don’t be a stranger!  In the meantime I’ll send a copy of your postcard to the local media I am sure they would love to hear from you.

Take Care laddy and Happy St. Patrick’s Day back atcha!



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