Each spring, the NFL kicks off its free agency period and has the NFL Draft. Both of those processes often turn NFL players – or soon-to-be-NFL players – into very rich men. In fact, the tens (and sometimes hundreds) of millions of dollars that many of these players are promised in their contracts are amounts the common person will never see in their lifetime.
But as any NFL fan knows: many of these contracts turn out to be bad business decisions, at least in hindsight. As the contracts in the NFL get bigger and bigger, the risk of teams giving players a contract they end up regretting increases as well. That inspired us to put together a list of the worst and most regrettable contracts in NFL history, the ones that have given teams a terrible case of buyer’s remorse.
David Boston
In 2003, Boston was an emerging star in the NFL as a wide receiver. After recording two straight seasons with over 1,150 yards receiving, Boston was a hot commodity heading into free agency. That’s why the Chargers signed Boston to a massive seven-year, $47 million contract. But it didn’t take long for things to turn ugly for the Chargers and Boston.
As his physical size increased to alarming proportions, rumors swirled that Boston was taking performance-enhancing substances. That might explain some of his antics, including a messy fight with a strength coach, and his generally “moody” demeanor. It was eventually announced that Boston tested positive for substances often used by bodybuilders. The Chargers released Boston just one forgettable season in that seven-year deal.
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