The left-handed golfer is known for rarely shying away from a money match, and his affinity for sports gambling is no secret, either. In 2001, he was reprimanded by the PGA Tour after winning $500 from Mike Weir in the players’ lounge at the NEC Invitational: Mickelson had wagered $20 at 25-1 odds that Jim Furyk would hole a bunker shot.

Mickelson has won far larger sums betting on major sporting events like the Super Bowl; three Las Vegas gaming sources told Outside the Lines that Mickelson still bets on sports in Vegas.