In the MLB, handing out massive contracts is always a gamble. With huge dollar signs on the line, teams have to balance big expectations with long-term risk—and sometimes, it just doesn’t pay off.
This article looks back at some of the most infamous contracts in MLB history—deals that, whether due to injuries, underperformance, or just plain bad luck, didn’t come close to living up to the hype.
15. Pablo Sandoval – Boston Red Sox
Pablo Sandoval signed a five-year, $95 million contract with the Red Sox in 2014. He struggled mightily, hitting just .237 with 14 homers in 161 games over three seasons. The Red Sox released him in 2017, eating about $49 million. Sandoval later admitted he regretted signing with Boston over staying in San Francisco.
14. Jayson Werth – Washington Nationals
Jayson Werth signed a seven-year, $126 million contract with the Nationals in 2010, shocking the baseball world. While he helped transform the team’s culture, his production declined significantly in later years. Werth averaged just 2.4 WAR per season during the contract, far below expectations for his massive salary.
13. Vernon Wells – Toronto Blue Jays/Los Angeles Angels
Vernon Wells signed a 7-year, $126 million contract with the Blue Jays in 2006, making him one of the highest-paid players in MLB. However, his performance declined significantly, hitting just .218 in his first season with the Angels after being traded. Wells’ contract is often cited as one of the worst in baseball history.
12. Prince Fielder – Detroit Tigers/Texas Rangers
Prince Fielder signed a nine-year, $214 million contract with Detroit in 2012, but played only two seasons before being traded to Texas. He retired in 2016 due to neck injuries, with Texas still owing him $9 million annually through 2020. Fielder’s contract became one of MLB’s most burdensome.
11. Ryan Howard – Philadelphia Phillies
Ryan Howard’s $125 million contract extension in 2010 became a burden for the Phillies. While he was a dominant force early in his career, injuries and declining performance plagued his later years. Howard earned over $190 million in salary, yet his production dropped significantly after 2011, making him one of baseball’s most overpaid stars.
10. Carl Crawford – Boston Red Sox
Carl Crawford signed a 7-year, $142 million contract with the Red Sox in 2010, but his performance plummeted. In his first season, he hit just .255 with 11 home runs and 18 stolen bases. Injuries further limited his playing time, and he was traded to the Dodgers in 2012, never living up to his massive contract
9. Mike Hampton – Colorado Rockies
Mike Hampton signed an eight-year, $121 million contract with the Rockies in 2000, the largest in baseball history at the time. His performance fell short of expectations, posting a 5.75 ERA over two seasons in Colorado. Hampton’s contract became notorious for its poor return on investment, especially considering the challenging pitching conditions at Coors Field.
8. Jacoby Ellsbury – New York Yankees
Jacoby Ellsbury signed a 7-year, $153 million contract with the Yankees in 2014 but played only 520 games over 4 seasons due to injuries. He missed the entire 2018 and 2019 seasons before being released, having produced just 9.8 WAR for his massive contract. The Yankees continued paying him through 2020, making him one of the most overpaid players in MLB history.
7. Chris Davis – Baltimore Orioles
Chris Davis signed a seven-year, $161 million contract with the Orioles in 2016, but his performance declined sharply. From 2017-2020, he hit just .185 with 54 home runs while earning over $17 million annually. Davis retired in 2021, still owed $42 million in deferred payments through 2037.
6. Jason Heyward – Chicago Cubs
Heyward signed an 8-year, $184 million contract with the Cubs in 2015 but failed to live up to expectations. Despite winning a World Series, his offensive production declined significantly. The Cubs released him in 2022, still owing $22 million. Heyward’s contract is widely regarded as one of the worst in MLB history.
5. Barry Zito – San Francisco Giants
Barry Zito signed a seven-year, $126 million contract with the Giants in 2007, the largest for a pitcher at the time. Despite his previous success, Zito struggled in San Francisco, posting a 4.62 ERA over seven seasons. He was even left off the 2010 postseason roster when the Giants won the World Series.
4. Josh Hamilton – Los Angeles Angels
Josh Hamilton’s $125 million contract with the Angels became a disaster. After stellar seasons with the Rangers, his performance plummeted in Anaheim. Injuries and substance abuse issues limited his playing time, while his batting average and power numbers declined sharply. The Angels ended up trading Hamilton back to Texas, agreeing to pay most of his remaining salary.
3. Miguel Cabrera – Detroit Tigers
Miguel Cabrera’s $292 million contract with the Tigers, signed in 2014, became one of MLB’s most criticized deals. Despite his Hall of Fame-caliber career, Cabrera’s production declined significantly in later years, failing to justify his $31 million annual salary. By 2023, he was primarily a designated hitter, far from the Triple Crown winner of 2012.
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2. Albert Pujols – Los Angeles Angels
Pujols signed a 10-year, $240 million contract with the Angels in 2012, but his performance declined significantly. From 2012-2021, he hit .256 with a .758 OPS, far below his Cardinals numbers. The Angels made the playoffs only once during his tenure, resulting in no postseason wins.
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1. Alex Rodriguez – New York Yankees
A-Rod’s 10-year, $275 million contract with the Yankees in 2007 set a record for the largest in MLB history. Despite his talent, the deal was criticized for its length and value. Rodriguez’s performance declined in later years, and he was suspended for the entire 2014 season due to PED use.
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