Jack Shepherd was a petty, pretty thief. He wasn't very good at it, so he got caught a lot. And he escaped a lot. Just like Henry More Smith. He, too, couldn't stop stealing and couldn't stop freeing himself from prison life. These guys prove that you can't keep a good (well, at least non-violent) man down.

The Good Bootlegger: Roy Olmstead
49:03

You Get an "A" For Effort: Beautiful Plans, Become Ridiculous Crimes
1:06:54

Here I Dreamt I Was an Architect: LEGO theft
1:00:52