The top 10 worst sports contracts ever

July 1 is widely recognized by Mets fans as Bobby Bonilla Day, a celebration that will continue through 2035 as the 59-year-old collects his $1,193,248.20 check from the team each time this year. 

Bonilla’s infamous deal is often considered the worst sports contract of all time, but the seemingly never ending agreement is in good company. Here’s a look at ten of the most egregious contracts to ever happen in sports.

Bobby Bonilla 

New York Mets, $1.2 million per year through 2035

Despite retiring from baseball in 2003 and not donning a Mets uniform since the 1999 season, Bonilla can expect a deferred payment of nearly $1.2 million in his mailbox on July 1, courtesy of his former ballclub. The deal, which sees Bonilla receiving payments every year from 2011 to 2035, came to fruition before the 2000 season, when the Mets released him and turned the remaining $5.9 million owed to him into $29.8 million.

If Bonilla were to take the field again, he’d immediately rank as the 20th-highest-paid player on the Mets active roster payroll, according to Spotrac.

Miguel Cabrera

Detroit Tigers, Eight years, $248 million (through 2023)

The Tigers inked their star first baseman to a long-term contract in 2016 following his decade of dominance. Cabrera produced MVP-winning seasons in 2012 and 2013, made 11 All-Star appearances and sports a career .310 batting average. However, the 39-year-old’s play quickly declined following his big payday. 

Cabrera mustered just 16 home runs in 529 plate appearances the year after signing his contract, later going on to miss much of the 2018 season due to hamstring and biceps injuries. Although Cabrera hasn’t lived up to his monumental deal in recent years, he sports a .300 batting average in 2022 and recorded his 3,000th hit earlier this season.

Gilbert Arenas

Washington Wizards, Six years, $111 million

The Wizards expected to get immediate production from Arenas when they signed him to the tune of $111 million in 2008. However, the former three-time All-Star was promptly sidelined with a knee injury, later receiving an indefinite suspension for bringing firearms into the Wizards’ locker room. 

Arenas has not been shy when discussing his abominable contract, even recognizing it’s likely one of the worst deals in NBA history. The Wizards put the agreement behind them after they paid Arenas his final check in 2017, seven years after he last played for them.

Joakim Noah

New York Knicks, Four years, $72 million

The Knicks clearly didn’t receive the memo from their New York neighbor, signing Noah to a $72 million deal on Bobby Bonilla Day in 2016. Despite being a two-time All-Star, the coveted free agent had missed 53 games the season before due to shoulder injuries and was already in decline. 

Noah appeared in just 53 games for the Knicks due to an assortment of injuries and a 20-game suspension for violating the NBA’s anti-drug policy. The big man was eventually released by the team in 2018, with the remaining guarantees in his contract being stretched over three years.

Albert Pujols

Los Angeles Angels, 10 years, $240 million

Pujols joined the Angels in 2011 after dominating the league for 11 years. Prior to earning his $240 million contract, the first baseman accumulated 455 home runs to go alongside a monstrous .328 career batting average and .420 on-base percentage.

The Angels knew they were taking a risk by signing Pujols, who was entering his age-32 season, to a 10-year contract. That risk didn’t pay off – Pujols’ on-base percentage plummeted, while his strikeouts skyrocketed. He is currently amidst a feel-good reunion season with the St. Louis Cardinals, the team he starred with before signing with the Angels.

Jacoby Ellsbury

New York Yankees, Seven years, $153 million

The Yankees snatched Ellsbury from the rival Boston Red Sox in 2014, but would ultimately come to regret that move.

When Ellsbury was able to stay on the diamond, the 38-year-old mightily struggled to mirror the production he displayed in his dominant final season with the Red Sox. After settling a contract dispute with the ailing veteran, the Yankees can kiss the failed signing goodbye.

Ilya Kovalchuk

New Jersey Devils, 15 years, $100 million

The Devils hoped to see Kovalchuk play in New Jersey for a long, long time when they signed the Russian left winger to an absurd 15-year contract that would’ve lasted until 2025. In fact, the organization hoped to lock up Kovalchuk for even longer, offering him a 17-year deal that was quickly vetoed by the NHL.

However, Kovalchuk’s time in New Jersey was short-lived – the hockey pro stepped away from the NHL in 2013, opting to play in the Russian KHL before making a return with the Los Angeles Kings in 2018. As for his former team, the Devils’ were fined $3 million and forced to forfeit draft picks after their attempts to sidestep the NHL’s contract rules.

Chris Davis

Baltimore Orioles, Seven years, $161 million

Davis earned a seven-year deal with the Orioles after displaying his powerful bat in several strong seasons with the organization. From 2012 to 2015, the star first baseman belted 159 home runs alongside a .256 batting average and .876 OPS.

Unfortunately for the Orioles, that all disappeared following his massive signing. The 36-year-old’s tenure in Baltimore was marred with strikeouts, slumps and an improbable 0-for-54 stretch. The veteran didn’t allow his contract to come to a fitting end, retiring from the MLB one year before its culmination in 2022.

Rick DiPietro

New York Islanders, $1.5 million per year through 2029

DiPietro secured a ludicrous 15-year contract from the Islanders, a deal that looked to be brilliant during its infancy. In the first two seasons playing under his new contract, the goaltender recorded a .911 save percentage and earned a spot on the 2008 All-Star team. This success, however, was short-lived. 

An array of injuries including a broken jaw, concussions and issues with his knees and groin handicapped DiPietro, who was only able to muster 50 appearances over the next five seasons. The Islanders waived him in 2013, but are reminded annually by the 16-year payout schedule which has them paying DiPietro $1.5 million a year.

Jay Cutler

Chicago Bears, Seven years, $126.7 million

The Bears had high hopes for Cutler, inking the quarterback to a seven-year contract with the hopes of finally finding their franchise quarterback. Those plans went awry, however, due to Cutler’s inconsistent play on the field – he led the league with 18 interceptions in 2014.

Cutler ultimately retired from the NFL following a disappointing 2016 season, later returning to the sport with the Miami Dolphins. A change of scenery ultimately didn’t do much for the quarterback, who officially called it quits in 2017.