Colin Montgomerie – 5
Colin Montgomerie holds the distinction as the “PGA Tour pro with the most second-place finishes at the majors without ever winning one.” His last chance to erase that label came during the same 2006 U.S. Open that saw Phil Mickelson falter at the end. Monty caught a 7-iron heavy from the middle of the 72nd fairway and made double bogey to tie with Mickelson and Jim Furyk, while Geoff Ogilvy raised the trophy.