5. "TERRIBLE" TOMMY O'CONNOR was convicted of killing a Chicago cop and was awaiting the hangman in 1921, but got ahold of a gun (possibly smuggled into jail in a pork chop sandwich) and escaped. He then did several car-jackings before disappearing for good. The good city of Chicago held onto the gallows until 1977 in hopes of using them to execute O'Connor, but he was never seen or heard from again.
6. NAT TURNER was a desperado, but also a freedom fighter. Guided by visions, he led a Virginia slave uprising in 1831 that massacred 55 whites before he was captured and hanged. In 1821, Turner had escaped slavery, but returned in order to free the slaves.
7. DILLINGER was behind bars when BONNIE PARKER and CLYDE BARROW were robbing banks. He became annoyed that they were hitting only small banks and complained that they were "giving bank robbing a bad name."
Well, there weren't ten.
Will the Real "Terrible" Tommy Please Stand Up? --Da Coot
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