Real name: Biff Dugan
First Appearance: Superman I#1 (Summer 1939)
Worst Act: Escaping prison
Created by: Jerry Sigel (writer) and Joe Shuster(inks/pencils)
Bit of odd one here. Superman number 1 was mostly the first few Superman yarns repackaged (with some added pages for a few), but tucked into the back was a short text story in which Superman fights Biff Dugan...sort of.
We start with Dugan already in jail, but Superman captures him when he escapes. Short, but it does show Superman dicking around with the police.