EVENT: 2006 U.S. Open
Lefty has a record five second-place finishes at the U.S. Open. In 2006, at Winged Foot, Mickelson was going for his third major in a row until he got back to his old ways. He held a one-shot lead going into the 18th hole, then he hit a trash can here, a tree branch there, and before you know it, he's tied for second and one shot short of a playoff. Nice guys don't always finish last, but they do come in second (a.k.a. the first loser) often.