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1
Jim Kelly
He went to four Super Bowls, set all the Buffalo records, out-dueled Steve Young in the greatest game never seen, and yet, never got the ring.
2
Allen Iverson
He put the Sixers on his back and led them to the 2000-01 Finals by himself (basically). Then, in the Finals, he gave us one of the greatest NBA moments ever (sorry Tyronn). That he never won it all is a crime.
3
Dan Marino
The Awards. The Legacy. But he only got to play in one Super Bowl where he ran into Joe Montana.
4
Tony Gwynn
The Padres have been to the World Series twice. In their history. Both times, it was because of Tony Gwynn. One of the greatest hitters of all time played for 20 years but never brought it all the way home. Well done, San Diego...
5
Barry Sanders
The greatest running back in NFL history never got to the mountaintop. In fact, he never even got to the Super Bowl. Some might put the blame on him for underperforming in the playoffs, but when you're the only true threat, teams shut you down.