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.
Did Charles Barkley gamble after the Super Bowl XLI bet that he claims to have won?
In May 2008, the Wynn Las Vegas casino filed a civil complaint against Barkley, alleging that he had failed to pay a $400,000 debt stemming from October 2007.
What else has Charles Barkley bet on besides the Super Bowl XLI bet?
During a trip to Las Vegas, he claims to have won $700,000 from playing blackjack in addition to the Super Bowl XLI betting.
Did Charles Barkley ever get together with other people?
Barkley spoke for many years of his Republican Party affiliation.
Are there any other interesting aspects about Charles Barkley's involvement with politics?
In July 2007, he made a video declaring his support for Barack Obama in the 2008 presidential election.

Question: What happened next?
Self-contained rewrite: What happened next after Charles Barkley declaring his support for Barack Obama in 2008?