10 of the All-Time Worst Contracts in Sports

Contracts in sports are an incredibly fascinating thing. Most players in professional sports play for the love of the game their whole lives until college, where – though they may get scholarships for

Contracts in sports are an incredibly fascinating thing. Most players in professional sports play for the love of the game their whole lives until college, where – though they may get scholarships for their athletic ability – they still earn absolutely nothing. If they’re skilled enough, they then transition into the professional leagues and start earning more than they could have ever dreamed of. Many professional athletes earn more in a year than the majority of people earn in their entire lives.

Sometimes, a big contract is worth it. For a player who is being courted by multiple teams, a team may have to sweeten the pot and pay a role player a little bit less in order to make room for the superstars. Sometimes, a player gets a smaller rookie contract until they truly prove their worth, at which point they sign another, much bigger contract.

Sometimes, contracts are just complete busts. It’s primarily because there’s no way to 100% accurately predict how a player will turn out. There are times where a team signs an incredibly promising young player to an astronomical contract, and he ends up being a bit of a disappointment, either because of his fumbling things on the court or field, or because of less than stellar behaviour in his free time. There are times when teams merely sign the player to a contract that’s far too long, forcing them to buy the player out or keep an ailing – or ageing – player on their team.

While most contracts are fairly uneventful, ordinary parts of the professional sports world, there are some cases where a contract is very memorable, for whatever reason that may be. At the end of the day, contracts are a tricky thing – here are ten examples where the teams had a few regrets after signing a certain contract.

10 Michael Vick

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There are a lot of very talented players in the NFL, but there are also a lot of players on every roster – not everyone can make a nine digit salary. Michael Vick was one of the lucky ones. He managed to snag a $130 million contract with the Atlanta Falcons in 2004, and then another gigantic $100 million contract with Philadelphia, with a $40 million guarantee as an incentive. Vick then forgot how to hold a football – by which I mean, he fumbled so much that he started to carry a football around with him everywhere so he’d be ready to guard against any team mates attempting to make him fumble. Sounds like something a rookie high school football player would do, not a quarterback signed to a $100 million deal. There’s also that whole thing about him being a convicted felon thanks to all that dog fighting. When you ink a $100 million contract, as a team, a fumbling felon isn’t exactly who you want signing those papers.

9 Justin Verlander

Rick Osentoski-USA TODAY Sports

In 2013, the Detroit Tigers signed Verlander to a seven year, $180 million contract, making him the highest paid pitcher in MLB history. He’s been underperforming at best since then, and his age can’t be ignored. He was hovering around the deadly 30 when he signed the contract, and will be nearly 40 when it finishes. Whether he tires out, gets taken out by injury, or merely plays average at best for the remainder of his career, it wasn’t the smartest contract for Detroit.

8 Matt Flynn

Kyle Terada-USA TODAY Sports

In 2012, the Seattle Seahawks were pretty desperate for a quarterback, and decided to sweeten the pot for Matt Flynn in order to lock him down. It was a three year deal worth just under $20 million – impressive, but nothing astronomical compared to some NFL contracts. However, a problem arose pretty quickly – while Flynn originally was expected to emerge as the starter in the quarterback pack consisting of Tarvaris Jackson, Russell Wilson and himself, Wilson soon blew the other two out of the water and became the starter. The Seahawks couldn’t drop Flynn fast enough after that, and traded him to the Raider just over a year after the ink on his original contract dried. He then shuffled between the Raiders, Buffalo Bills and Green Bay Packers. His most recent contract was a meager 1 year, $1.07 million – far less than his former $20 million deal. The Seahawks may have regretted that original contract, but they're probably pretty happy with having Wilson instead of Flynn now.

7 Allan Houston


Ever wonder if you could get paid even if you just sit on the bench? Ask Allan Houston. This basketball player signed a six year, $100 million contract, and had two good years of playing time. He wasn’t an absolute superstar, but he was a good enough player that his salary may have been an alright decision. However, he began to have a lot of knee problems. Consequently, he did not play a single game in the last two years of his contract – but the Knicks had to keep paying. He received millions for sitting and watching the game, something that countless fans were doing at home for free. Although it wasn't really his fault because of injuries, teams should definitely consider a player's injury proneness when signing a player.

6 Ilya Kovalchuk

Ed Mulholland-USA TODAY Sports

Ah, salary caps. At one point in his career, Ilya Kovalchuk signed a $100 million contract. How long, you might ask – five, six years? No. Kovalchuk signed a contract that stretched a whopping 15 years – more than many professional athletes’ entire careers. And that was after the original 17 year, $102 million deal was rejected for being just too damn long. The Devils initially got bit for their attempts as the NHL penalized them for the original offer, which was an attempt to circumvent the salary cap. The NHL eventually offered the Devils some leniency on their punishment, as Kovalchuk retired from the NHL only a few years after the debacle, choosing to go play in Russia.

5 Gilbert Arenas


Arenas got a six year, $111 million contract, and many fans were rooting for him – he was absolute dynamite on the court, burying shots from all over the place. He was a top ten scorer for three years in a row, a stat that made his huge contract seem almost completely worth it. Then, he pulled out guns in the Wizards changing room – literally one of the stupidest decisions a professional athlete could make. Then his knees started to get a little troublesome. He’s now playing basketball in China, because no NBA team would touch him with a ten foot pole, and his old team is still struggling with some of the consequences of their Arenas decision. That’s one contract that must sting a little.

4 JaMarcus Russell



Sometimes, a promising player ends up out of the league due to circumstances outside of his control, like with a serious injury. This isn’t the case when it comes to JaMarcus Russell. Russell was snapped up first overall in his draft year and was thought to be the Oakland Raiders’ golden ticket. He signed a six year, $68 million deal, an absolutely astounding figure for a player with no NFL playing time. It was a huge risk to give a rookie such a massive contract – but it wasn’t the only thing that got a little too big. Russell’s weight constantly fluctuated towards the higher end of the scale and at one point, during an off season, he went up to nearly 300 pounds. His performance off the field became increasingly worse, and finally after an arrest for illegal substance possession, the Raiders let him go. He banked nearly $40 million in his three average-at-best seasons, making it a contract the Raiders were likely very angry about signing.

3 Albert Pujols

Kelley L Cox-USA TODAY Sports

Most professional sports are plagued by the salary cap, a restriction that limits what contracts can be signed and forces management to cleverly juggle things around. That rule doesn’t quite apply to baseball, meaning there are quite a few contracts that are far higher than they should be. One example – Albert Pujols. His contract entitles him to a whopping $254 million, but what is perhaps even more shocking is that it keeps him on the roster past his 40th birthday. Every athlete is different, but the age of 30 is a bit of a red flag for many professional athletes, let alone 40. No matter how good you are, age affects athletes, making it foolish to pay tens of millions of dollars for someone who very well may be unable to play well – if at all – in the final years of his contract.

2 Amar'e Stoudemire

David Richard-USA TODAY Sports

For awhile, Amar'e Stoudemire was like a giant concrete statue that the Knicks couldn’t get rid of, no matter how hard they tried. In 2012, no one wanted to pay out the $65 million remaining in his contract as his knee made him a risky choice. The Knicks had to keep him on the roster while he underwent several surgeries to help fix his knees, and rode the bench for many games due to his injuries. And, to make it worse, he isn’t insured for injury, making him a ticking time bomb that no team wants to touch. Luckily for the Knicks, Stoudemire is in the last year of contracts and they'll have some relief next off-season.

1 Rick DiPietro

Anthony Gruppuso-USA TODAY Sports

With NHL contracts, from Kovalchuk to DiPietro, there’s a pretty clear message – don’t sign away decades. Regardless of how good a player is at any given point, a few years can make all the difference in the world when it comes to professional sports. Goaltender Rick DiPietro made a reasonable yearly salary in his contract, about $4.5 million a year. However, consider the length – the Islanders signed him for an astounding 15 years. That’s longer than some careers! After signing the contract in question in 2006, he was bought out in 2013 thanks to his injuries, meaning he played less than ten years of his contract. It cannot be emphasized enough – don’t sign players to contracts more than a decade in length. It just never works out.

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10 of the All-Time Worst Contracts in Sports