He's been playing chess tournaments and posting about them on 2+2.
Seriously.
Some Tournament Games
He has a prop bet to "beat Howard (Lederer) in a single chess game in one year."
Allen was a beginner when the prop bet was made in March. Howard was nearly master level strength when he last played in the '80s.
Cunningham Prop Bet
I'm sure he's been playing some poker to.