12. Mike Mussina, 2001: Six Years, $88.5 Million
Mike Mussina somehow managed to pitch well for the Yankees, embellish his Hall of Fame career, and never win a World Series with the team.
He joined the Bombers as the coup of the 2000-01 offseason, flashing his old stuff in both 2001 (143 ERA+) and 2003 (130 ERA+), but mixing a few fringe-average seasons in there as the team struggled to recapture their dynastic glory in October.
His signature Yankee moment came in relief in Game 7 of the 2003 ALCS, when he held the fort in an entirely unfamiliar situation, allowing the Yankees to ultimately rally against Pedro Martinez and Grady Little's idiocy.
Over eight years in the Bronx, he won 20 games once: his final season, 2008.