Free agency is one of the most crucial aspects of Major League Baseball, allowing teams to bolster their rosters with superstar talent. However, not every deal pans out as expected.
Some contracts become burdensome due to injuries, underperformance, or simply misguided decision-making. Here’s a look at the 15 worst free-agent contracts in MLB history.
15. Chris Davis – Baltimore Orioles (2016, 7 years, $161 million)
Davis had a monster 2013 and 2015, hitting over 40 home runs each season. The Orioles rewarded him with a massive contract, but he soon became one of the least productive hitters in baseball. His .168 batting average in 2018 was historically bad, making this deal a complete disaster.
14. Jacoby Ellsbury – New York Yankees (2014, 7 years, $153 million)
Ellsbury never replicated his 2011 MVP-caliber season after joining the Yankees. Injuries and inconsistency plagued him, and the Yankees ultimately released him before the deal expired, paying him to not play.
13. Jason Heyward – Chicago Cubs (2016, 8 years, $184 million)
While Heyward’s defense remained elite, his offense never justified the contract. Despite a famous rain-delay speech during the Cubs’ 2016 World Series run, his bat was a liability for most of his tenure in Chicago.
12. Albert Pujols – Los Angeles Angels (2012, 10 years, $240 million)
Pujols was one of the best hitters in MLB history when the Angels signed him, but he was past his prime. While he still hit some milestones, his declining production and bloated contract hurt the franchise.
11. Carl Crawford – Boston Red Sox (2011, 7 years, $142 million)
Crawford was a star in Tampa Bay but never found success in Boston. Injuries and poor play led to an early exit, as he was eventually traded to the Dodgers.
10. Barry Zito – San Francisco Giants (2007, 7 years, $126 million)
Zito was a Cy Young winner in Oakland, but his performance with the Giants was mediocre at best. While he had a heroic moment in the 2012 postseason, the overall contract was a major overpay.
9. Josh Hamilton – Los Angeles Angels (2013, 5 years, $125 million)
Hamilton was an MVP with the Rangers, but after joining the Angels, he struggled mightily. Injuries and personal issues led to his release, and the Angels even paid part of his salary while he returned to Texas.
8. David Wright – New York Mets (2013, 8 years, $138 million)
Wright was a franchise icon, but injuries robbed him of his career. While not a bad player when healthy, he played in just 77 games from 2015 to 2018 before retiring.
7. Mike Hampton – Colorado Rockies (2001, 8 years, $121 million)
Hampton was supposed to be the Rockies’ ace, but Coors Field was unforgiving. He lasted just two years before being traded and never lived up to expectations.
6. Prince Fielder – Detroit Tigers (2012, 9 years, $214 million)
Fielder was productive early in the contract but was soon traded to Texas. A neck injury ended his career prematurely, making this deal a costly mistake.
5. Pablo Sandoval – Boston Red Sox (2015, 5 years, $95 million)
Sandoval never came close to justifying his contract. Poor conditioning and performance led to his eventual release, and he returned to the Giants for a fraction of the cost.
4. Mo Vaughn – Anaheim Angels (1999, 6 years, $80 million)
Vaughn was a dominant hitter in Boston but struggled in Anaheim. Injuries and weight issues derailed his career, and he was traded after two seasons.
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3. Stephen Strasburg – Washington Nationals (2019, 7 years, $245 million)
After a historic 2019 World Series MVP performance, Strasburg inked a massive extension. However, injuries limited him to just eight starts from 2020 onward before an early retirement.
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2. Alex Rodriguez – Texas Rangers (2001, 10 years, $252 million)
Rodriguez put up monster numbers, but the contract was too much for Texas to handle. They traded him to the Yankees in 2004, and while he remained productive, the deal set a bad precedent.
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1. Bobby Bonilla – New York Mets (1999, Deferred Contract)
Bonilla’s contract is infamous because of its deferred payment structure. The Mets have been paying him $1.19 million annually since 2011 and will continue until 2035, making it the worst contract from a financial standpoint.
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