Conversation so far:
How did Charles Barkley handle gambling?
Barkley is known for his compulsive gambling. Despite suffering big losses, Barkley also claims to have won on several occasions playing blackjack and betting on Super Bowl XLI.
Who won Super Bowl XLI Charles Barkley betted on?
Barkley was betting on the Indianapolis Colts to defeat the Chicago Bears in Super Bowl XLI of 2006 and claims to have won.

Question: Did he gamble after the Super Bowl bet?
Self-contained rewrite: Did Charles Barkley gamble after the Super Bowl XLI bet that he claims to have won?