on the shady

Committing acts, usually frowned upon or being something you wouldn't express outright to friends and acquaintances.

Hidden and not in plain sight. Kept secretive and between individuals. Avoiding deterioration of character and their images.
Invokes large quantities of trust between individuals to not break their bond and trust.

James was always the go-to guy for whenever Craig wanted something on the shady. Like nude photos or a blowjob.