2. Charles Barkley
Chuck is notorious for his gambling losses.
According to Charles Barkley, he has lost $1 million dollars gambling on 30 different occasions, including numerous sports bets loses and tough luck at the tables.
Barkley recalled his single most devasting loss was betting on the Falcons to beat the Patriots in Super Bowl 51.
Charles Barkley was kicking back on the couch and relishing in what appeared to be a soon-to-be victory with the Falcons up 28-3 in the 3rd quarter.
Chuck was watching the game with some former pro NFL players, including former Falcons receiver Roddy White. It was after a Pats touchdown in the 4th quarter White said, “uh oh” out loud. A nervous Chuck asked White why he said that, and White told him the Falcons were going to blow it.
Sure thing, the Falcons had an epic collapse and blew the game 34-28, costing Charles Barkley $100,000.