Baseball is a sport of long-term investments, and over the years, MLB teams have handed out massive contracts to players expected to become franchise cornerstones.
However, not every big payday translates into on-field success. Some players struggle with injuries, poor performance, or unexpected declines, leaving teams with costly regrets. Here’s a look at 20 MLB stars who signed massive contracts but failed to deliver.
1. Chris Davis – Baltimore Orioles (7 years, $161 million, 2016)
After leading the league in home runs twice, the Orioles rewarded Davis with a monster deal. Unfortunately, his production plummeted, and he became one of the worst hitters in baseball before retiring.
2. Albert Pujols – Los Angeles Angels (10 years, $240 million, 2012)
Pujols was a generational talent with the Cardinals, but his production in Anaheim never matched his massive salary. He remained a solid hitter but was far from the MVP-caliber player the Angels expected.
3. Miguel Cabrera – Detroit Tigers (8 years, $248 million, 2016)
Cabrera was an elite hitter, but this extension came at the tail end of his prime. Injuries and declining performance made the latter years of the deal a major burden on Detroit’s payroll.
4. Jason Heyward – Chicago Cubs (8 years, $184 million, 2016)
Heyward’s defense was elite, but the Cubs signed him expecting offensive production that never came. His struggles at the plate made this contract one of the most disappointing in recent memory.
5. Jacoby Ellsbury – New York Yankees (7 years, $153 million, 2014)
The Yankees hoped Ellsbury would replicate his Red Sox success, but injuries derailed his career. He played just four seasons in New York before being released.
6. Stephen Strasburg – Washington Nationals (7 years, $245 million, 2020)
Strasburg was the 2019 World Series MVP, but after signing his massive extension, injuries limited him to just a handful of starts before his career effectively ended.
7. Prince Fielder – Texas Rangers (9 years, $214 million, 2012)
Fielder was a dominant hitter, but his time in Texas was cut short due to a career-ending neck injury, making his contract a financial disaster for the Rangers.
8. Carl Crawford – Boston Red Sox (7 years, $142 million, 2011)
Crawford was a speedster with Tampa Bay, but his time in Boston was a disaster. He underperformed and was eventually traded to the Dodgers in a salary dump.
9. Josh Hamilton – Los Angeles Angels (5 years, $125 million, 2013)
Hamilton was an MVP with Texas, but his Angels tenure was marked by injuries and inconsistency. His struggles led to a trade back to the Rangers.
10. Yoenis Céspedes – New York Mets (4 years, $110 million, 2017)
Céspedes was electric when healthy, but injuries, including an infamous accident involving a wild boar, kept him off the field for most of his contract.
11. Barry Zito – San Francisco Giants (7 years, $126 million, 2007)
The Giants expected Zito to be an ace, but he struggled for most of his contract. He rebounded to contribute in the 2012 postseason, but overall, he failed to justify his massive deal.
12. Matt Kemp – Los Angeles Dodgers (8 years, $160 million, 2012)
Kemp was an MVP runner-up in 2011, but injuries and declining production turned his long-term deal into a financial headache for the Dodgers.
13. Hanley Ramírez – Boston Red Sox (4 years, $88 million, 2015)
Ramírez was brought in to add offensive firepower, but he struggled defensively and never found consistency at the plate.
14. Robinson Canó – Seattle Mariners (10 years, $240 million, 2014)
Canó was still productive but not at the level Seattle paid for. A PED suspension further tainted his tenure, and he was eventually traded.
15. David Price – Boston Red Sox (7 years, $217 million, 2016)
Price had some strong moments, including a key role in the 2018 World Series, but injuries and inconsistency made this deal a disappointment for the Red Sox.
16. Troy Tulowitzki – Toronto Blue Jays (10 years, $157 million, 2011)
Injuries robbed Tulowitzki of his All-Star abilities, and he barely played in the latter half of his contract.
17. Pablo Sandoval – Boston Red Sox (5 years, $95 million, 2015)
Sandoval never lived up to his contract and was eventually released, making this one of the worst free-agent signings in Red Sox history.
18. Mark Teixeira – New York Yankees (8 years, $180 million, 2009)
Teixeira had one strong season but battled injuries for most of his contract, failing to meet expectations.
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19. Eric Hosmer – San Diego Padres (8 years, $144 million, 2018)
Hosmer was a World Series hero in Kansas City, but his production with the Padres was mediocre, making his contract one of the biggest overpays in recent history.
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20. Jordan Zimmermann – Detroit Tigers (5 years, $110 million, 2016)
Zimmermann was an All-Star with Washington, but injuries and poor performance turned his Detroit tenure into a nightmare.
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