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Who has the most regrettable sports contract?

Updated: August 1, 2010, 1:51 PM ET
By Jonathan Raber

Before any more general managers get carried away with doling out huge sums of money, they might want to take a look at what we think are some of the most regrettable contracts in sports history.

10. Rick DiPietro (New York Islanders, 2006) 15 years, $67.5 million

Fans in New York that haven't had a chance to see DiPietro in action firsthand need not fret, there's ample time. The Islanders will fork out $4.5 million a season to the injury-prone goaltender until 2021.

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