On September 1, the Houston Texans and star defensive end J.J. Watt agreed to a six-year extension that could be worth up to $100 million. It’s a well-deserved raise for the NFL’s reigning Defensive Player of the Year, and by all accounts should end up being a very favorable deal for the Texans going forward. After all, when you have a chance to lock up a franchise cornerstone long-term, you have to do it. Right?

Well, not necessarily.

There have been just over 100 contracts handed out in sports whose total value could exceed $100 million, and not many of them end up working out. Sure, sometimes a guy like Calvin Johnson or Tim Duncan will come along and validate the absurd salaries, but for every one of them there are far more cautionary tales like Gilbert Arenas or Michael Vick.

Whether it’s through their play on the field, injuries, or off-field activities, it seems that in addition to their athletic skills these $100 million players have a unique talent for self-sabotage. In honor of Watt (who will hopefully not become a new member of this list), here are The 25 Worst $100 Million Contracts in Sports History.

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