This is Mr. Amos Holloman, who was a career robber, with a record spanning at least 34 years (1910-1944).

Holloman spent most of his life behind bars, plotting how to get out from behind bars, and being recaptured. In between, he was quite a prolific robber. The amount of time he did suggests he was not a particularly talented robber.

I was only able to find his mugshots from Nebraska but he did quite a bit of robbing in Oklahoma, Montana, Missouri, and Iowa, so no doubt there are more floating around out there!