Superstar talent doesn’t last forever, but that hasn’t stopped teams across professional sports from handing out massive contracts to aging players well past their prime.
Sometimes, it’s a loyalty deal; other times, it’s an overestimation of how long a star can sustain elite production. Whatever the reasoning, these deals often become financial nightmares, handicapping franchises for years. Here are 15 of the worst contracts ever given to aging superstars.
15. Albert Pujols (Los Angeles Angels – 10 years, $240 million, 2012)
At the time, Albert Pujols was a three-time MVP and one of the greatest hitters in baseball. But by the time his contract expired, his tenure with the Angels was widely regarded as a disaster. While he had a few solid seasons, he never lived up to the massive deal and struggled with injuries and declining production.
14. Kobe Bryant (Los Angeles Lakers – 2 years, $48.5 million, 2013)
Kobe is a Lakers legend, but giving him this contract extension after a devastating Achilles injury was more about loyalty than basketball sense. The deal crippled the Lakers’ ability to rebuild, keeping them in mediocrity until his retirement.
13. Alex Rodriguez (New York Yankees – 10 years, $275 million, 2008)
A-Rod was still productive in the early years of this deal, but it became an albatross when injuries and a PED scandal overshadowed his late career. The Yankees had to eat a massive chunk of his salary, and by the end, they were simply paying him to go away.
12. Chris Davis (Baltimore Orioles – 7 years, $161 million, 2016)
Davis was coming off a monstrous 47-homer season when the Orioles gave him this deal. He quickly fell off a cliff, posting one of the worst contracts in MLB history, even going an infamous 0-for-54 stretch at the plate in 2019.
11. Russell Westbrook (Los Angeles Lakers – 5 years, $205 million, 2017)
Westbrook’s deal was originally with the Thunder, but it became a nightmare for every team that traded for it. By the time the Lakers acquired him, his athleticism had declined, and his fit next to LeBron James was a disaster.
10. Miguel Cabrera (Detroit Tigers – 8 years, $248 million, 2014)
Miggy was a two-time MVP, but this extension kicked in when he was already in his 30s. The back half of the contract was brutal, with declining production and injuries turning it into a massive burden for Detroit.
9. Albert Haynesworth (Washington Redskins – 7 years, $100 million, 2009)
This wasn’t just one of the worst aging contracts—it was one of the worst free-agent signings ever. Haynesworth completely flamed out after getting paid, showing little motivation and clashing with coaches before being cut just two years later.
8. Blake Griffin (Detroit Pistons – 5 years, $173 million, 2017)
The Clippers handed Griffin this contract, then immediately traded him to the Pistons. Injuries caught up with him, and Detroit was stuck paying a max contract to a player who could no longer dunk.
7. Amar’e Stoudemire (New York Knicks – 5 years, $100 million, 2010)
Stoudemire was dominant for about half a season before injuries turned this contract into dead weight. The Knicks were stuck paying him huge money despite chronic knee problems that limited his effectiveness.
6. Joe Flacco (Baltimore Ravens – 6 years, $120.6 million, 2013)
Flacco got this deal right after a Super Bowl win, but he was never an elite QB. His play declined quickly, and the contract hamstrung the Ravens until they finally moved on.
5. Derrick Rose (Chicago Bulls – 5 years, $94 million, 2011)
The youngest MVP in NBA history, Rose received this extension before devastating injuries derailed his career. While his downfall wasn’t his fault, the Bulls were stuck with an untradeable contract for years.
4. Todd Gurley (Los Angeles Rams – 4 years, $57.5 million, 2018)
Gurley was an MVP-caliber running back, but his knees betrayed him almost immediately after signing this deal. The Rams had to eat a massive amount of dead money when they cut him just two years later.
3. Chris Paul (Houston Rockets – 4 years, $160 million, 2018)
Paul was still good, but Houston regretted this deal almost immediately. His injuries and declining athleticism made it clear that paying him $40 million per year into his late 30s was a mistake.
2. Bobby Bonilla (New York Mets – Deferred contract, $29.8 million, 2000)
Bonilla’s contract wasn’t massive, but it’s infamous. Instead of paying him $5.9 million upfront, the Mets deferred payments, meaning they’ve been paying him over $1 million annually every July 1st since 2011—and will continue until 2035.
1. Stephen Strasburg (Washington Nationals – 7 years, $245 million, 2019)
Strasburg’s contract quickly became an absolute disaster. After leading the Nationals to a World Series win, he signed this massive deal—only to pitch just 31.1 innings over the next four seasons due to injuries. Washington is still paying him to not play.
