By the end of the third season, he is reduced to blind, deaf, toothless torso, and works as an illegal medical experiment subject, on an inescapable long-term contract.
In the fifth season, twenty years in the future, he has gambled his physical brain away, and lives on as a computer simulation based on a brain scan, in a modified musical birthday card fished out of a wastebasket.
In the sixth season, he loses the card and his brain pattern is loaded into a nanobot and set to work cleaning cholesterol deposits out of the arteries of a convenience store janitor.
In the eighth season, he has gambled away his nanobot body and is set to work in a attoparticulate waldo, guiding helium-3 atoms to collide and fuse to provide power in the battery of a pizza delivery scooter.
In the ninth season, things really go to shit for him.