Top 10 Most Insane Sports Contracts

Although he displayed some talent on the ice while he was with Ottawa in the ‘90s and early noughties, Alexei Yashin’s off the ice antics made him one of the most hated players in the league. In fact, he was frequently booed both away and at home. It was no shock when the Senators shipped him off to Long Island in 2001, who gave up two players and the second overall draft pick to get him and quickly signing him to a ten year $85-plus million contract. Yashin’s talent quickly evaporated and the Islanders were stuck with an underperforming and despised player whose enormous contract left them no cap room.

With a 4-2 MMA record, Kimbo Slice’s signing by Bellator MMA in January 2015 initially seemed perfectly reasonable. However, Slice’s last fight was actually a loss, which came way back in 2010, making boxer and mixed martial artist a forty-one year old fighter who hadn’t fought in five years. While he headlined Bellator 138, and won the June 2015 match, his victory was over Ken Shamrock, who was even further past his prime and deemed an unworthy opponent by many at an astounding fifty-one years old. Unless Slice plans to exclusively fight athletes that are middle-aged or older, his MMA future could be bleak.

Without a salary cap in baseball, there is often a tendency to sign anyone hot to a huge contract, without thinking of the long term consequences. That’s precisely what happened when the New York Yankees penned a five year $82.5 million contract for the former Toronto Blue Jays player A.J. Burnett. In New York, Burnett struggled mightily, rarely posting a winning record during the season and failing to close out the 2009 World Series, which was eventually done a game later by teammate Andy Pettitte. Eventually, the Yankees traded Burnett to Pittsburgh with New York still paying 20 of the $33 million left on his contract.

LA Galaxy made international news when they signed perhaps the most famous football player in the English speaking world in 2007 for a hefty sum. However, fame doesn’t always transfer to talent, as Beckham arrived hurt and long past his prime. His time in LA was marred by frequent injuries and he drew the ire of fans who referred to Beckham as a fraud. Although the Galaxy captured multiple championships during his tenure, they were owed much more to players like Landon Donovan and Robbie Keene while Beckham’s biggest contribution was likely jersey sales.

It’s hard to pinpoint what exactly the biggest regret for the Washington Wizards was after signing this overrated player to a six year $111 million contract in 2008. It could have been the many injuries he suffered, or his general lack of effort that led to his downfall. However, most people would agree that it was Gilbert Arenas’ decision to bring unloaded guns into the locker room, which got him charged with a felony, and saw him suspended for a majority of the season. In 2010, Arenas was traded to the Orlando Magic, where he was quickly waived, came off the bench for the Memphis Grizzlies and was last signed to the Shanghai Sharks in 2012.

At the beginning of his career, Mike Hampton actually showed some promise, but not so much as to deserve an 8-year $121 million contract. And in the year 2000, this was the biggestcontract in sports history. Once getting to Colorado, his production quickly fell off a cliff. In his two seasons there, he had an ERA of 5.75, and the Rockies sent him to the Florida Marlins, after which he was quickly traded to Altanta. His time on the Braves was largely spent off the field as he had back-to-back Tommy Johns surgeries and missed two full seasons.

In the early nineties, Bobby Bonilla was the highest paid player in baseball, thanks to a 5 year $29 million contract. But that wasn’t the insane part. The crazy part came when the New York Mets wanted to part ways with him, but still owed him $5.9 million. Instead of paying him out, the Mets negotiated a new deal where he would instead be paid roughly $1 million a year, plus interest… for twenty-five years. The deferred payments began in 2011, meaning Bonilla is still being paid more than a few star Mets pitchers, and will be until 2035 when the buyout will have cost them close to $30 million.

The New Jersey Devils, who had traded to acquire Ilya Kuvelchuck, were keen to keep their new star when he became an unrestricted free agent. They were so eager in fact that they penned a 17 year $102 million contract, which not only broke the record for longest contract in NHL history, but it circumvented the league’s salary cap rules. As a result, the Devils were fined $3 million and lost draft picks, with the contract cut reduced two years and two million dollars. After a few less than productive years, Kuvelchuck left the NHL for good, heading back to play in his native Russia.

The Yankees have a long rich history of throwing barrels of money at players, but a ten year $275 million contract for A-Rod was terrible even by their standards. Rodriguez was already in his thirties when he penned this contract, meaning that he would be on the Yankees’ books until his early forties. While signing any aging star this long is insane, getting one with a history of steroid suspicion is what lands him in this high spot. To the surprise of very few, A-Rod was eventually busted for using performance-enhancing drugs and was suspended an entire season.

Before we reveal our top pick, here are a few honorable mentions:

Ilya Bryzgalov
-Philadelphia Flyers (NHL)

CM Punk
-UFC

Allan Houston
-New York Knicks (NBA)

Wade Redden
-New York Rangers (NHL)

Not satisfied with the money they had wasted on Yashin, in 2006, the Islanders signed their goalie to a contract for 15 years, something they had tried a year earlier, but were blocked by the NHL for obvious reasons. Rick DiPietro was hardly a household name, and struggled with injuries both before and after the $67.5 million signing. He had only one All-Star appearance, never won a playoff game, was sent down to the minor league, and finally had his contract bought out with a enormous eight years still remaining.