He lost 4 super bowls
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Jim McMahon in Super Bowl XX.
Jim McMahon of the Bears in Super Bowl XX.
1) Super Bowl XI - WR Fred Biletnikoff 2) Super Bowl XV - QB Jim Plunkett 3) Super Bowl XVIII - RB Marcus Allen
Yes, Jim Caldwell of the Colts made it this year.
Super Bowl XI: Ken Stabler, Oakland Raiders Super Bowl XV: Jim Plunkett, Oakland Raiders Super Bowl XVII: Joe Theismann, Washington Redskins Super Bowl XVIII: Jim Plunkett, Oakland Raiders Super Bowl XX: Jim McMahon, Chicago Bears Super Bowl XXI: Phil Simms, New York Giants Super Bowl XXII: Doug Williams, Washington Redskins Super Bowl XXV: Jeff Hostetler, New York Giants Super Bowl XXVI: Mark Rypien, Washington Redskins Super Bowl XXXI: Brett Favre, Green Bay Packers (not yet eligible) Super Bowl XXXIV: Kurt Warner, St. Louis Rams (not yet eligible) Super Bowl XXXV: Trent Dilfer, Baltimore Ravens (not yet eligible) Super Bowl XXXVII: Brad Johnson, Tampa Bay Buccaneers (not yet eligible) Since Super Bowl XXXVI, besides Brad Johnson, the remaining Super Bowl winning QBs are still active. The 4 not yet eligible have been retired for less than 5 years.