15 Worst Contracts in Sports History

Upon retiring in 2016, Kobe Bryant made a record $323 million in career salary earnings, and while Los Angeles probably doesn’t regret a large part of that, it was the latter chunk of paying for his time at the Staples Center that probably makes them wince. For his final two seasons, he signed a two-year $48.5 million contract extension. Sadly, they plagued by injuries that sidelined the legendary player. To put it plainly: the household name was paid like a superstar and played like anything but. 

We all know how beleaguered the hapless New York Knicks are, but there was a time when Phil Jackson was heralded as a savior. When the former Chicago Bulls and Los Angeles Lakers mastermind headed to Madison Square Garden in 2014, he signed a big fat five-year contract worth $60 million, with many hoping he’d be able to turn the team around. Yet despite Jackson’s involvement, the Knicks have continued to spiral out of control and suddenly that $60 million seems like a big fat waste. Regardless, Knicks owner James Dolan defended his contract with Jackson earlier this year during an interview with sportscaster Michael Kay. “Three years ago, I signed a contract with Phil Jackson – the man who has more championship rings, as far as I know, than anybody else,” he noted. “He was the best guy we thought we could find to run the New York Knicks, and I made an agreement with him, and the agreement didn’t say that you have to have this amount of wins by this time or anything of the sort.” Well, okay then!

We all know Jay Cutler is a dope – but least he’s a filthy rich one. Widely considered one of the worst deals in NFL history, the Chicago Bears had high hopes for their former golden boy when he signed contract extension worth $126.7 million bucks over a period of seven years in 2014. Cutler’s subsequent play on the field was erratic at best and he left the NFL and retired from football after a disappointing 2016 season. 

You know the drill by now. A promising athlete is given a boatload of money and they wind up underperforming and making off like a bandit. DeAngelo Hall fits the classic story to a tee after the cornerback signed a seven-year contract with the Oakland Raiders. Hall only played eight games with the team because, well, he stunk, making a cool million bucks per game. In the real world, if you suck at your job you’re fired. In the reality that is the NFL, you wind up scoring a slick seven digit paycheck. Isn’t pro-sports wonderful?

Long before the news that Michael Vick was in talks with Atlanta to sign a one-day contract in order to officially retire as a Falcon, the quarterback signed two fat contracts that wound up burning both the Falcons, and later the Eagles. In Atlanta, Vick made headlines with what was supposed to be a ten year, 130 million dollar deal that, despite his skill on the field, fizzled when the QB was imprisoned for 23 months for that whole dogfighting mess. After his release from the slammer, Philadelphia snapped up Vick in 2009 with high hopes he’d triumph in the City of Brotherly Love and guaranteeing a cool 40 million bucks. Instead, Vick failed to live up to expectations and he departed for the Jets in 2014. 

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. 

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. 

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.

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 

$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. 

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.”

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.

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.

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.