Fans want the owners of their favorite team to open the checkbook and spend big to get them closer to a championship. Nothing frustrates them more than someone who is more concerned about the bottom line than about success on the field. So spend that extra million, or 10, to land the big name on the market, and get us that ring.
Of course, the only thing worse than a stingy owner, in the eyes of the fanbase, is a big-money bust. No one gets booed harder than the player who was signed to be the franchise savior and has instead become part of the problem, handicapping the front office’s financial flexibility with a bloated contract that’s impossible to trade, and failing to live up to that price tag on the field.
From the time that the first free agents began inking deals and cashing in, the first flops became the targets of fan ire. Here are the worst of the worst—the biggest busts in sports history. Here are the worst contracts ever signed in athletics.
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5 Ilya Kovalchuk, New Jersey Devils
Hockey contracts typically aren’t as large, or as infuriating, as the other major sports, but don’t tell that to New Jersey Devil fans. The team signed Kovalchuk to a nine-figure deal in 2010, virtually unheard of in the NHL. And for good reason. Things went bad almost from the outset.
The $102 million contract was for a total of 15 years. Why would any team sign an athlete for the unreasonably long contract term of fifteen years? Because the league wouldn’t let them sign him for 17. The Devils tried to do just that, only to get fined $3 million and surrender draft picks as punishment for trying to circumvent the NHL’s salary cap.
He was 27 years old at the time, so it was unlikely that he would stick around the NHL until age 42, which is when the Devils were committed to paying him until. He didn’t. He announced his retirement three years later, then went back to Russia to play before making a brief NHL comeback in 2018.
A close runner-up is the 15-year deal Rick DiPietro signed with the Islanders in 2006. He also didn’t make it until the end of it, and the buyout has the Islanders still paying him $1.5 million a year until 2029.
4 Ben Simmons, Philadelphia 76ers
The top pick in the 2016 draft, Simmons was supposed to be the face of the franchise and lift the Sixers to new heights. That’s why Philly signed him to a five-year deal worth $177.2 million.
He wasn’t a good match for the infamous Philadelphia fans, who were infuriated over his shyness when it came to putting up shots, including passing on a shot during crunch time of a critical playoff game. He also battled injury during his 76ers career and finally sat out a season as he attempted to force the team to trade him.
3 Stephen Strasburg, Washington Nationals
One of the biggest MLB prospects in recent memory, the highly-touted Strasburg arrived in Washington and became an instant star. He lived up to the hype, winning 18 games in 2019 and leading the Nats to a World Series championship. He was also named MVP of the World Series, and, in what seemed like perfect timing for him, it came just before his contract with the team expired.
Unwilling to let their World Series hero walk, Washington signed him to a seven-year deal worth $245 million. Instead of giving the franchise more on-field heroics, he’s instead given them an anatomy lesson, suffering from carpal tunnel, thoracic outlet syndrome and a host of other ailments. He finally retired this year after pitching a total of eight games and 31.1 innings on that new contract.
2 Deshaun Watson, Cleveland Browns
There is really nothing to like about the contract Watson signed with Cleveland in 2022. Watson was persona non grata in Houston, where he had developed into a rising star at quarterback, because a total of 22 massage therapists filed civil suits against him alleging sexual misconduct.
Just the mere fact that the Browns were willing to trade for Watson and extend him left many fans with negative feelings about the whole deal. But the more you look into the specifics of the five-year, $230 million contract, the worse it makes everyone involved come off.
First, the entire deal is guaranteed, something that was virtually unheard of in the NFL and set a dangerous precedent for all contracts to come, at least in the eyes of the team owners. Second, it paid Watson just $1,035,000 in base salary for the first year, then jumped to $46 million per season for each of the next four years. Why the odd structure? Because Watson and the Browns were assuming he’d be facing an NFL suspension for all his alleged massage misdeeds, and they were making sure he didn’t have to forfeit too much money.
Of course, as the saying goes, teams would be willing to sign Hitler to a contract if he could play. So Watson could outplay all the initial criticism of the contract. Not so much. Between injury and suspension, he’s played in just 10 of Cleveland’s 24 games over the contract so far and has almost as many interceptions (8) as touchdowns (11).
1 Bobby Bonilla, New York Mets
The poster child for the bad contract, Bobby Bo signed a five-year, $29 million contract with the team in 1991. It doesn’t sound like much now, but at the time, it set the record for largest contract in pro sports. The team traded Bonilla midway through the deal, allowing him to win a World Series (and sign an extension) with the Marlins in 1993.
He returned to the Mets, and they released him while still owing him $5.9 million for the last year. Rather than paying up, they agreed to defer payments, with 8% interest. So, every year, from 2011 until 2035, when Bonilla will be 72 years old, the Mets issue him a check for $1.2 million. That’s why July 1, the day the check is cut each year, is known as Bobby Bonilla Day across sports.
