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1) Matt Cassel
In 2008, something shocking happened: Tom Brady suffered a season-ending knee injury in the very first game of the season. Matt Cassel bravely stepped in and almost led tham back to the playoffs at 11-5, eventually just coming up short via tiebreaks.
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Come 2009, he parlayed that into a starting opportunity. The Brock Huard era hadn't gone very well at Arrowhead, so new general manager Scott Pioli traded for his old charge (and linebacker Mike Vrabel) as soon as free agency began.
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What happened with that? Three losing records in four seasons, and the one time they made the playoffs, they lost to the Baltimore Ravens. The nadir was going 2-14 in 2012-13, which led Pioli to ditch Cassel and trade for Alex Smith.
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