I started a B/X campaign a month ago that I'm calling Deep Valley. The idea was to start fresh and design some things based on images only. So I spent a few days picking art that I love - such as paintings and drawings by Rodney Matthews, Hannes Bok, and Eyevind Earle to name a few - and writing short things inspired by them. I wrote a bunch of character classes and asked my players to choose from them instead of anything standard.
This class emerged from that idea. It's my riff on the sly Jack from Jack Tales stories. This class sort of stands in the place of the Thief in the Deep Valley setting, which has a strong faerie tale falvor (I hope).
Here's a PDF of the Jack class and screen shots below. This is formatted to digest size.