There was the on-the-spot wager he made with a mouthy fan at Augusta. She did log 11 top finishes overall, three second-place finishes.ancient roman gambling dice SECOND LIFE GAMBLING SCRIPT As Keegan Bradley found out firsthand, his story is exactly the reason you never want to play Phil Mickelson for money. We've heard some great golf gambling stories involving Phil Mickelson through the years. There's the time he schooled Paul Azinger. The time. Phil Mickelson may be the most notorious gambler in golf history, self when asked about a recent gambling story that was widely circulated.