Phil Proves That Nice Guys Can Finish First

Celeb(s): Phil Mickelson
When: August 2000
Wager: $20,000
Event: Baltimore Ravens 2000 season winning the Super Bowl

Before the start of the 2000-2001 NFL season, golfer Phil Mickelson placed a $20,000 bet on the Baltimore Ravens, who happened to be 28-to-1 underdogs to win the Super Bowl. The reason? "I liked their off-season player acquisitions." Much to everyone's surprise (except for the clairvoyant Mickelson), the Ravens ended up defeating the New York Giants, 34-7, in Super Bowl XXXV. Mickelson ended up taking home $560,000. #racksonracksonracks