10 Expensive Deals in MLB History That Failed Unexpectedly

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MLB contracts come with a major risk because they are fully guaranteed. Franchises expect players to stay healthy and perform well for many years when they spend millions of dollars on a player.

However, when deals fail, they can hurt a team’s finances and limit its ability to sign other players. There are several reasons big contracts go wrong. Some players suffer serious injuries that affect their careers. Others experience sudden drops in performance and struggle to live up to expectations.

Let’s take a look at 10 such instances.

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10. Pablo Sandoval

Pablo Sandoval managed just 161 total games with a .235 average in Boston. - Source: Imagn — Pablo Sandoval managed just 161 total games with a .235 average in Boston. – Source: Imagn

Pablo Sandoval agreed to a five-year, $95 million contract with the Boston Red Sox on Nov. 23, 2014, and signed the deal the next day. The Red Sox intended to bring in the clutch, postseason switch-hitting that helped him win three World Series with the San Francisco Giants.

However, Sandoval’s defensive ability at third base and bat speed waned after arriving in Boston. After just 161 games, the Red Sox released him in 2017.

9. Barry Zito

Barry Zito signed a seven-year, $126 million deal with the San Francisco Giants on Dec. 28, 2006. It was the richest contract ever handed to a pitcher at the time.

Zito’s signature sweeping curveball and fringe velocity were effective during his time with the Oakland Athletics. However, the pitch lost its effectiveness after his move to the Giants, and he allowed more walks and home runs. He posted a losing record in six of his seven seasons with the Giants.

8. Carl Crawford

Carl Crawford struggled heavily under the pressure of Boston and hit just .255 before injuries derailed his mechanics. - Source: Imagn — Carl Crawford struggled heavily under the pressure of Boston and hit just .255 before injuries derailed his mechanics. – Source: Imagn

Carl Crawford signed a seven-year, $142 million contract with the Boston Red Sox on Dec. 11, 2010. He had earned four All-Star selections, a Gold Glove Award and a Silver Slugger Award with the Tampa Bay Rays from 2002 to 2010.

Moreover, Crawford was a four-time AL stolen base leader. However, the pressure in Boston affected him. Wrist and elbow injuries further affected his performance. The Red Sox had to offload him to the Los Angeles Dodgers in a salary-dump trade less than two seasons into the contract.

7. Jacoby Ellsbury

Jacoby Ellsbury's elite speed and defense quickly eroded under a cascade of hip, oblique, and foot injuries. - Source: Imagn — Jacoby Ellsbury’s elite speed and defense quickly eroded under a cascade of hip, oblique, and foot injuries. – Source: Imagn

Jacoby Ellsbury signed a seven-year, $153 million contract with the New York Yankees on Dec. 7, 2013. The Bronx Bombers poached him from the Boston Red Sox for his defense and speed.

However, oblique strains, plantar fasciitis and hip surgeries eroded his speed. He did not play after the 2017 season. The Yankees released him before the 2020 season.

6. Chris Davis

Chris Davis suffered an unprecedented offensive collapse that included an infamous 0-for-54 slump, forcing an early retirement. - Source: Imagn — Chris Davis suffered an unprecedented offensive collapse that included an infamous 0-for-54 slump, forcing an early retirement. – Source: Imagn

Chris Davis agreed to a seven-year, $161 million contract extension with the Baltimore Orioles on Jan. 16, 2016. He signed the contract on Jan. 21, 2016.

Davis led the MLB in home runs in 2013 and 2015. However, he lost his timing and plate discipline after the contract extension. He went 0-for-54 in consecutive at-bats from Sep. 14, 2018 to April 13, 2019. Moreover, he finished the 2019 season with a modern-era worst .168 batting average.

Injuries in the later years prompted him to retire in August 2021. Baltimore will pay $42 million in deferred payments through 2037.

5. Kris Bryant

Kris Bryant's tenure in Colorado has been a disaster, with nine separate injured list stints restricting him to just 170 games. - Source: Imagn — Kris Bryant’s tenure in Colorado has been a disaster, with nine separate injured list stints restricting him to just 170 games. – Source: Imagn

Kris Bryant signed a seven-year, $182 million contract with the Colorado Rockies on March 18, 2022. The Rockies intended to make Bryant the new marquee face of the franchise, but what happened was something else.

Bryant landed on the injured list nine separate times in his first four seasons with back, foot and side ailments. He has never played more than 80 games a season with the Rockies. Moreover, Bryant missed the entire 2026 season due to injuries. He only played 11 games in 2025.

4. Prince Fielder

Prince Fielder suffered severe, recurring herniated discs in his neck that required multiple spinal fusion surgeries, forcing an early retirement at age 32 - Source: Imagn — Prince Fielder suffered severe, recurring herniated discs in his neck that required multiple spinal fusion surgeries, forcing an early retirement at age 32. Source: Imagn

Prince Fielder signed a nine-year, $214 million contract with the Detroit Tigers on Jan. 26, 2012. The Tigers traded Fielder to the Rangers before the 2014 season for Ian Kinsler.

After the trade, Fielder suffered severe injuries. Recurring herniated discs in his neck required multiple spinal fusion surgeries. Moreover, doctors declared him unable to play in 2016. He was only 32 at the time. The Tigers and Rangers split the remaining $100M guaranteed contract.

3. Albert Pujols

Albert Pujols' elite production vanished almost immediately after joining the Angels due to severe plantar fasciitis and lower-body degeneration. - Source: Imagn — Albert Pujols’ elite production vanished almost immediately after joining the Angels due to severe plantar fasciitis and lower-body degeneration. – Source: Imagn

Albert Pujols signed a 10-year, $240 million contract with the Los Angeles Angels on Dec. 8, 2011. He achieved historic milestones with the Angels, but his performance was a far cry from his elite production with the St. Louis Cardinals.

Severe plantar fasciitis and lower-body degeneration sapped his lower-half power. He also lost his agility. He was a below-average hitter for the Angels, and the team designated him for assignment in his final season.

2. Anthony Rendon

Anthony Rendon's contract became one of the worst in baseball history as a relentless cycle of major injuries limited him to a dismal .231 average and an average of under 52 games per season. - Source: Imagn — Anthony Rendon’s contract became one of the worst in baseball history as a relentless cycle of major injuries limited him to a dismal .231 average and an average of under 52 games per season. – Source: Imagn

Anthony Rendon signed a seven-year, $245 million contract with the Los Angeles Angels on Dec. 11, 2019. Rendon had a starring role in the Washington Nationals’ 2019 World Series triumph.

However, hip, wrist and hamstring injuries stripped away his elite hitting ability. Moreover, his public comments about lacking motivation garnered a negative reception from fans.

Rendon only played five seasons with the Angels before he agreed to restructure his contract after the 2025 season. He never played more than 58 games a season with the Angels. Rendon will receive the remaining $38 million in deferred payments.

1. Stephen Strasburg

Severe thoracic outlet syndrome limited Stephen Strasburg to just eight starts and 31.1 innings over the life of the contract before forcing his medical retirement. - Source: Imagn — Severe thoracic outlet syndrome limited Stephen Strasburg to just eight starts and 31.1 innings over the life of the contract before forcing his medical retirement. – Source: Imagn

Stephen Strasburg signed a seven-year, $245 million contract extension with the Washington Nationals on Dec. 9, 2019. He was the World Series MVP when the Nationals won the 2019 Fall Classic.

Strasburg developed thoracic outlet syndrome almost immediately after the contract extension. He pitched just 31.1 innings across eight starts before a complex nerve surgery effectively ended his pitching career.

Edited by Joseph Schiefelbein

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