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15 Worst Contracts in Sports History

From the Mets paying Bobby Bonilla a million a year until 2035 to Notre Dame giving Charlie Weis close to $20 million to walk away

Worst Contracts in Sports

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The contract is a mere piece of paper that, when signed, can seal fates, make careers and birth legends. That’s the idea, anyway. Unfortunately, throughout the recent history of sports there are some contracts that, well, were just awful ideas in hindsight. From players who never realized their full potential to slick agents who negotiated a lopsided agreement, here are 15 of the downright worst contracts in sports.

Allan Houston

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Allan Houston, New York Knicks

Houston successfully scored his Knicks a slot in the 1999 NBA playoffs thanks to an incredible shot that will go down in New York basketball history. As a result, the team rewarded him with a rich six-year contract worth 100 million big ones. Unfortunately after a mere two decent seasons, Houston was sidelined by a knee injury and his once-promising career quickly evaporated. Adding insult to injury (literally), Houston was the NBA’s second-highest paid player despite in both 2006 and 2007- despite not playing a single game either season. 

Gilbert Arenas

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Gilbert Arenas, Washington Wizards

Even Gilbert Arenas admits he signed one of the worst contracts in NBA history. After inking a six year, $111 million contract with the Washington Wizards back in 2008, the former three time All-Star found himself quickly sidelined by a knee injury and suspended due to his not-so bright idea to bring some guns into the locker room. It wasn’t until this past October that the embattled player received his final check from the Wizards, despite not wearing a Washington jersey since 2010. 

Josh Hamilton

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Josh Hamilton, Texas Rangers

Slugger Josh Hamilton has the dubious distinction of being one of the worst free agent signings in Major League Baseball history. That’s because after four seasons with the Texas Rangers, the North Carolina native was paid a whopping $125 million in a five year deal by the Angels, only to almost immediately underperform and quickly find himself sidelined by both a shoulder injury and drug addiction. After a mere three seasons in sunny Anaheim, Hamilton was traded back to Texas. Later shipped off to the minors, the once-promising player was subsequently released by the Rangers earlier this year.

Isiah Washington

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Isiah Thomas, New York Knicks

If you’re a Knicks fan and you’re looking for someone to blame for their recent history full of L’s, one person to furrow your brow toward is former president Isiah Thomas. Between 2003 and 2008, the beleaguered Thomas paid out $120 million bucks to a bunch of players who didn’t play, handing out bad contracts like popcorn at MSG. By the time Thomas departed the team had a whole lot of nothin’ to show for it, with their winning percentage the fifth lowest in Knicks history 

Charlie Weis

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Charlie Weis, Notre Dame

$18,967,960. That’s how many George Washingtons former Notre Dame coach Charlie Weiss scored due to a sweet Fighting Irish buyout deal, the result of five years as head coach of the school’s embattled program. Fired in 2009 and succeeded by Brian Kelley, Weiss was paid handsomely to go on his merry way; a deal all the more bitter considering bolstering Weiss’s wallet probably isn’t the smartest way to spend the university’s hard-earned tuition cash. 

Albert Haynesworth

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Albert Haynesworth, Washington

Haynesworth was a promising NFL player when he scored 100 million bucks from Washington, only to play just 20 games and bid adieu. Apparently, it was Haynesworth’s plan all along to get paid a bucketload and say sayonara, which is probably why fellow former Redskin Chris Cooley once called Haynesworth an “awful human being,” telling the Washington Post in 2013: “His goal was to come here, make a large signing bonus and then get released and not have to do any of the work.”

Ilya Kovalchuk

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Ilya Kovalchuk, New Jersey Devils

The NBA, MLB and NFL aren’t the only leagues awash in shitty contracts. Case in point: the tale of Russian NHL ace Ilya Kovalchuk who signed a 15 year (!) $102 million dollar contract with the Devils that wasn’t supposed to wrap up until 2025. Regardless of the fact the team tried their best to skirt around the league’s pesky salary cap rules, the hockey pro decided to walk away from the NHL altogether at the ripe old age of 30 and play in his motherland of Russia. Ilya left with a bundle of cash, only to now reportedly eye a return to his former team. Time will only tell if Kovalchuk will make a deal with the Devil(s) once again.


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Alex Rodriguez, New York Yankees

The embattled former Yankee should get on his hands and knees everyday to thank his lucky stars for the negotiating skills of superagent Scott Boras. That’s because over the course of his turbulent career, Boras successfully netted $448 million for the former star; $317 million from the Yanks alone, including one of the richest contracts in baseball history. While the team did score a World Series ring in 2009 with A-Rod in tow, the majority of the slugger’s twelve seasons as a Bronx Bomber was spent embroiled in scandal or marred by underperformance, ending with the player departing the team last summer with little notice and no fanfare. Oddly enough, A-Rod fired Boras in 2010.

JaMarcus Russell

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JaMarcus Russell, Oakland Raiders

Poor JaMarcus Russell is widely considered to be one of the NFL’s biggest draft busts ever – and for good reason. As the first overall pick in 2007, Russell entered the league a hero, joining the Oakland Raiders who were hungry for a star. He left, however, after three disappointing seasons, and getting away with a cool $32 million in guaranteed cash. A sad addendum: with the NFL long in his rearview mirror, the former QB got the itch to return to the league last year and penned letters to various teams offering to play for free. Not a single one bit