The Curious Case of Dean Winchester. Oh Dean old Dean!
Synopsis: Dean and Sam discover a witch (guest star Hal Ozsan) is running a high-stakes poker game where the currency is life years vs. money. Bobby (Jim Beaver) sees the game as a chance to get out of the wheelchair and bets 25 years, but loses. As Bobby begins to age rapidly, Dean steps in to save him but also ends up turning into an old man, leaving Sam holding the bag for their survival. Episode written by Sera Gamble & Jenny Klein and directed by Robert Singers.