Jim Kelly
Jim Kelly is best known for being the only quarterback to start in 4 consecutive Super Bowls, but his making this list actually has very little to do with that. He quarterbacked some great teams and was always solid in the regular season, but was usually not at his best during the playoffs, which may be a big part of the reason he never won a Super Bowl.
Kelly was drafted by Buffalo in 1983, but he had no desire to play for the Bills, so he signed on with the USFL's Houston Gamblers, where he set league records for passing that nobody else was close to, but when the league folded in 1986, he had no choice but to join Buffalo.
The Bills were struggling through the rebuilding process for his first couple of seasons in Buffalo, but starting in 1988, they would make the playoffs 8 times in 9 seasons. He peaked in 1990, when he led the Bills to a 13-3 record, best in the AFC, and led the league with a 63.3% completion percentage while throwing a career-low 9 interceptions.
That season was the only time he played well in the playoffs, throwing for 639 yards and 5 touchdowns in the first two games, which earned Buffalo its first-ever Super Bowl berth. Kelly was solid in the Super Bowl, throwing for 212 yards, but did not throw a touchdown, and the Bills lost at the last moment when Scott Norwood missed the winning field goal with 8 seconds left in the game.
The following season he led them back to 13-3, and they again made the Super Bowl, but it was in spite of Kelly, who threw for only 390 yards, 3 touchdowns, and 5 interceptions in the two games leading up to the big game. He added 4 more picks in the Super Bowl as the Bills lost to Washington 37-24.
In 1992 he missed the first two playoff games due to injury, including the biggest comeback in playoff history and a blowout upset of the Steelers. He returned in time to help Buffalo upset Miami, but struggled in the Super Bowl, throwing 2 picks before going down again and being replaced as Dallas ran away 52-17.
It was more of the same in 1993, as Buffalo advanced to the Super Bowl threw for only 447 yards and 2 touchdowns in the first two playoff games, then again failed to throw a touchdown in the Super Bowl as they fell to Dallas again, this time 30-13.
He played another 3 years, making two more playoff appearances, but he lost his best chance at a title when that kick missed in his first trip to the big game. He never played up to his potential again in the playoffs, and that is a big part of the reason that he isn't ranked higher on this list, but he was good enough in all those years of leading Buffalo to the playoffs that he has to be part of this countdown.
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