Last Updated: June 17th, 2026 by Michael Schatz
From record-breaking contracts to legendary payment plans that still make headlines today, baseball has seen its fair share of financial missteps. Here’s a look at the 11 most overpaid players in MLB history, whose massive contracts didn’t quite match their on-field performance.
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Albert Pujols: Angels’ $240 Million Gamble
The Angels’ 10-year, $240 million investment in Albert Pujols in 2012 marked one of baseball’s most significant financial miscalculations. Despite hitting career milestones including his 500th and 600th home runs, Pujols’ production declined dramatically. His batting average dropped from .328 with the Cardinals to .256 with the Angels, while the team made just one playoff appearance during his tenure.
Bobby Bonilla: The Never-Ending Payday
The infamous “Bobby Bonilla Day” represents one of baseball’s most peculiar financial arrangements. Every July 1st until 2035, Bonilla receives $1.19 million from the Mets for a contract bought out in 2000. The deal, initially tied to Bernie Madoff’s investment scheme, will result in a total payout exceeding $29.8 million for a player who hasn’t played since 2001.
Chris Davis: The $161 Million Strikeout
After a 47-homer season in 2015, Davis signed a massive 7-year, $161 million contract with the Orioles. His performance collapsed spectacularly, culminating in a .168 batting average in 2018 – the lowest ever for a qualified hitter. He set an MLB record with an 0-for-54 streak before retiring in 2021, while still receiving $17 million annually through 2037.
Pablo Sandoval: Boston’s $95 Million Panda Problem
The Red Sox’s investment in “Kung Fu Panda” turned disastrous when they signed him to a 5-year, $95 million deal. Sandoval appeared in just 161 games over three seasons, batting a mere .237 with 14 home runs. Weight issues and injuries plagued his tenure, leading to his release in 2017 while still owed $48 million.
Jason Heyward: Cubs’ $184 Million Defensive Specialist
The Cubs’ 8-year, $184 million investment in Heyward never paid off offensively. While he contributed to their 2016 World Series victory, his batting average of .245 with the Cubs fell well below expectations. Despite his excellent defense, the contract value far exceeded his contributions, leading to his release before the final year.
Jacoby Ellsbury: Yankees’ $153 Million Bench Warmer
The Yankees’ 7-year, $153 million commitment to Ellsbury yielded just four active seasons. Injuries sidelined him for his final three years while still collecting his full salary. His performance declined significantly from his Red Sox years, and he never hit above .271 in pinstripes before his release in 2019.
Mike Hampton: Colorado’s $121 Million Mountain of Regret
Hampton’s record-breaking 8-year, $121 million contract with the Rockies in 2001 quickly became a cautionary tale. His 5.75 ERA in Colorado led to a trade after just two seasons, but the Rockies continued paying portions of his salary for years, making it one of baseball’s worst pitching investments.
Josh Hamilton: Angels’ $125 Million Disappointment
Hamilton’s 5-year, $125 million contract with the Angels yielded just two seasons of underwhelming performance. He hit .255 with only 31 home runs total before personal issues and injuries derailed his career. The Angels traded him back to Texas in 2015, agreeing to pay most of his remaining salary.
Carl Crawford: Boston’s $142 Million Speed Bust
Crawford’s 7-year, $142 million contract with Boston produced just 161 games over two injury-filled seasons. His .260 batting average and mere 14 stolen bases fell far short of his Tampa Bay numbers. The Red Sox traded him to the Dodgers in 2012 but continued paying portions of his massive contract.
Barry Zito: Giants’ $126 Million Cy Young Gamble
The Giants’ 7-year, $126 million investment in Zito, then the largest ever for a pitcher, failed to deliver expected returns. His ERA jumped from 3.55 with Oakland to 4.62 with San Francisco. Despite a memorable 2012 postseason performance, his overall record of 63 wins over seven seasons didn’t justify the massive contract.
David Price: Red Sox’s $217 Million World Series Gamble
The Red Sox made David Price one of baseball’s highest-paid pitchers with a 7-year, $217 million contract in 2016. Despite helping secure the 2018 World Series championship, his tenure was plagued by injuries and inconsistent performance. When traded to the Dodgers in 2020, Boston agreed to pay half his remaining salary, making each of his starts cost approximately $1 million.