John Elway
The end of John Elway’s career ended up erasing a ton of postseason shortcomings that Elway had for the majority of his career as the starting quarterback of the Denver Broncos. Considered the most heralded quarterback prospect to ever come out of college, Elway ripped the hearts out of certain opponents (like the Cleveland Browns), but came up short in the Super Bowl three times in four years.
In Super Bowl XXIV, Elway and the Broncos were on the wrong end of a 55-10 loss, the most lopsided margin of defeat in Super Bowl history. Even with his two eventual Super Bowl wins, many argue that Elway benefitted from a stout defense combined with a Hall of Fame running back (Terrell Davis); those critics will point to the fact that Elway finished with 21 interceptions in 21 postseason games.