50. Drew Bledsoe
Unfortunately for Drew Bledsoe, his career may be remembered most for losing his job to a man named Tom Brady. Before an injury allowed Brady to secure the job from Bledsoe, the talented quarterback started 123 games for the Patriots between 1993-2001. Bledsoe was a three-time Pro Bowler with the Pats — twice leading the league in completions (’94, ’97). The Washington native would go on to earn a fourth Pro Bowl bid while with the Buffalo Bills before ultimately finishing his playing career with the Cowboys.
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49. Doug Williams
After spending the first five seasons of his career with the Tampa Bay Buccaneers, Doug Williams joined the Washington Redskins and promptly made NFL history. In 1987, Williams made two regular season starts — and lost both. Despite the losses, Williams was given the offensive reigns when the Redskins entered the playoffs. Williams rewarded coach Joe Gibbs’ faith and led Washington to a 42-10 victory over John Elway and the Denver Broncos in Super Bowl XXII. Williams finished the contest 18-of-29 for 340 yards and four scores — making history as the first African-American starting quarterback to win a Super Bowl.
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