The Worst Sports Contracts of All Time, Ranked

This summer has been an eye-opening experience for the sports fanatic in all of us thanks to the NBA free agency period. A whopping $3 billion was spent on the first day of free agency in order to secure some of the league’s most highly touted free agents, such as Kevin Durant, Kyrie Irving, Jimmy Butler and Kemba Walker.

With that amount of money circulating in the league right now, many fans and experts can imagine the amount of loot superstars such as LeBron James and Kawhi Leonard may ask for when they test the free agency waters in the summer of 2020. But not every multimillion-dollar deal is a win-win situation for both parties. Some contracts have made it seem like the franchises flushed their money down the toilet, thanks to superstar athletes not meeting up to the expectations of the front office. 

Based on insane contractual agreements and players’ underachievements, here’s our list of the worst sports contracts of all time.  

Hoops’ alleged “savior” turned out to be one of the biggest disappointments in NBA front office history. The mastermind behind the “triangle offense” that led to dynasties in Chicago and L.A. couldn’t get it done in the Big Apple. Many thought signing Jackson to a five-year, $60 million deal would be an amazing investment, but it backfired. In his second year as president of basketball operations, the Knicks went 17-65. 

By his third year, he drafted Kristaps Porzingis but later decided to let go fan-favorite Carmelo Anthony. By June 2017, he and the Knicks mutually decided that he would step down from the position—adding to the long curse of losing seasons and disappointing die-hard fans like Spike Lee.

Arguably the biggest draft bust not only in NFL history but throughout the four major sports leagues, JaMarcus Russell’s superstar potential created a way for him to earn big bucks without ever performing on the gridiron. The former LSU Tigers standout walked away with a whopping $32 million in guaranteed cash while compiling a record of 7-18 during his three seasons with Oakland.

When the Chicago Bears signed the former Vanderbilt University standout to a seven-year, $126 million contract extension in January 2014, Bears fans scratched their heads in confusion. In a season riddled with injuries, Cutler finished 2013 as a starter with a 5-6 record. But what made things worse is that Cutler was coming off a season where he led the NFL in interceptions.

Meet the owner of a contract so bad that a new rule had to be installed in the league’s collective bargaining agreement that would change free agency forever.

When Gilbert Arenas became a free agent after 2003, he signed with the Washington Wizards after the Golden State Warriors couldn’t match the offer sheet due to salary cap restrictions. This gave birth to the Gilbert Arenas Provision, which allows NBA franchises to offer and re-sign restricted free agents who were not drafted in the first round.

Fast-forward to 2008, fresh off another amazing All-Star season, Washington and Arenas agreed to a six-year, $111 million deal. 

After the Wizards signed the scoring sensation, the three-time All-Star played just 13 games the season following his eye-popping deal. His distractions off the court, such as being suspended indefinitely for keeping an unloaded gun inside the locker room, raised red flags for the organization. But what put the icing on the cake was his disappointing play during the 2010-2011 season where he finished last in field goal percentage amongst guards by shooting a horrific 36.6% from the field. 

“When the amnesty kicked in, they were allowed to expand the contract,” Arenas explained to TMZ Sports about his deal when he was traded to the Orlando Magic in 2011. “So I’m still getting paid until 2016.” 

Currently retired from the league, Arenas’ money is so long that he came out and said, “I could spend every penny I have in the bank and I still have $38 million coming.”

Talk about laughing all the way to the bank.

Bobby Bonilla’s deal with the New York Mets is the reason why July 1 is an unofficial holiday in sports. Bonilla is the owner of arguably the contract steal of the century, in which the New York Mets agreed to a deferred payment agreement after owing him $5.9 million from the 2000 season. The kicker is that the Mets and Bonilla’s agent, Dennis Gilbert, were able to agree to defer the payment of the money for ten years by adding an 8% annual interest rate to the deal. If you do the math, that means the Mets agreed to pay Bonilla up to $29.8 million until 2035.

The Mets have paid him exactly $1,193,248.20 every July 1 for the past six years. And every July 1, until 2035, the Mets will be sending Bonilla a check-in that amount instead of just buying him out when they had the opportunity after the 2000 season. 

This is insane considering Bonilla hasn’t suited up for an MLB game since 2000. Getting more than a million dollars added each year to his $46.45 million career earnings as a six-time MLB All-Star and a World Series champion for the Florida Marlins is what you can consider “retirement plan” goals!