14. Jim Kelly
Jim Kelly is the only NFL quarterback to take his team–in this case, the Bills of Buffalo–to four straight Super Bowls, and not even Tom Brady has accomplished that feat. Kelly’s misgiving was coming up short in all four ultimate contests, in which he threw but two touchdowns versus seven interceptions.
In our postmodern “win or you’re nothing” culture, it’s easy for cynics to dismiss Kelly, but he actually came oh-so-close to winning the Bills’ first Super Bowl (XXV) versus the New York Giants, and had a halftime lead in their final Super Bowl (XXVIII), a rematch against the Cowboys. Had Kelly but split his four Super Bowls, he would be much more highly regarded, and receive more credit for being a master of the Bills’ “K-Gun” no-huddle offense.