Last Updated: June 17th, 2026 by Michael Schatz
Baseball contracts can make or break a team’s future. From ill-timed mega-deals to investments that seemed sound at the time, here are the 10 most regrettable contracts in Major League Baseball history. These cautionary tales have shaped how modern teams approach free agency and long-term commitments.
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Chris Davis’s $161 Million Nightmare (Baltimore Orioles)
After leading the league with 47 home runs in 2015, Davis signed a massive 7-year, $161 million contract. What followed was a historic collapse, including a .168 batting average in 2018 – the lowest ever for a qualified hitter. The Orioles are still paying Davis through 2037 due to deferred money, making this contract one of baseball’s most catastrophic investments.
Bobby Bonilla’s Never-Ending Payday (New York Mets)
The infamous Bobby Bonilla contract turned $5.9 million into annual payments of $1.19 million from 2011 to 2035, totaling $29.8 million. The Mets made this arrangement believing their investments with Bernie Madoff would outperform the contract’s interest rate. Now, “Bobby Bonilla Day” on July 1st has become an annual reminder of this notorious deal.
Albert Pujols’ $240 Million Angels Disappointment
After dominating with the Cardinals, Pujols signed a 10-year, $240 million deal with the Angels in 2012. Despite hitting his 500th and 600th home runs, his performance declined dramatically. His batting average dropped below .250 multiple times, and his OPS+ fell below league average. The Angels ultimately released him in May 2021 before the contract’s completion.
Miguel Cabrera’s Costly Extension (Detroit Tigers)
The Tigers signed Cabrera to an 8-year, $248 million extension when he was already 33. Despite reaching milestone achievements like 3,000 hits and 500 home runs, his performance declined sharply due to injuries and age. His final seasons saw him hitting below .250 with diminished power, making him one of the most expensive designated hitters in baseball history.
Jacoby Ellsbury’s $153 Million Yankees Bust
After starring for the Red Sox, Ellsbury signed a 7-year, $153 million contract with the Yankees. His tenure was plagued by injuries, missing the entire 2018 and 2019 seasons. He played just 520 games over four seasons, producing a mere 9.0 WAR before being released prior to the final year of his contract.
Jason Heyward’s $184 Million Cubs Gamble
Despite contributing to the Cubs’ 2016 World Series victory and maintaining elite defense, Heyward’s 8-year, $184 million contract never paid off offensively. He hit just .245 with minimal power during his Cubs tenure, leading to his release before the final year of his deal, despite his legendary Game 7 rain delay speech.
Robinson Cano’s PED-Tainted $240 Million Deal
Cano’s 10-year, $240 million contract with the Mariners became a disaster due to multiple PED suspensions and declining performance. The Mariners eventually traded him to the Mets, but not before paying a significant portion of his salary. His suspensions and rapid decline made this one of the worst long-term investments in baseball history.
Pablo Sandoval’s $95 Million Red Sox Failure
“Kung Fu Panda” signed a 5-year, $95 million contract but played just 161 games over three seasons in Boston, hitting a meager .237. The Red Sox released him in 2017, eating the remainder of his contract. His -2.0 WAR while earning nearly $100 million stands as one of the worst returns on investment in MLB history.
Josh Hamilton’s $125 Million Angels Tragedy
Hamilton’s 5-year, $125 million contract with the Angels became a cautionary tale when personal struggles and injuries limited him to just 240 games over three seasons. The Angels traded him back to Texas in 2015, agreeing to pay most of his remaining salary for virtually no return, marking one of baseball’s most tragic contract stories.
Carl Crawford’s $142 Million Red Sox Disappointment
Crawford’s 7-year, $142 million contract became a disaster when his speed and athleticism vanished after signing with Boston. He hit just .260 in two seasons before being traded to the Dodgers, where he continued to struggle. The contract became a warning about signing speed-dependent players to long-term deals in their late prime years.