The 20 Worst Contracts In MLB History, Ranked In Order

The 40 Worst Contracts In MLB History – These Contracts Left Fans Shaking Their Heads - Gameday News
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The 40 Worst Contracts In MLB History – These Contracts Left Fans Shaking Their Heads
Baseball |
4/13/26
At some point in every Major League Baseball team's history, a player is signed to a massive contract and fails to deliver the excitement fans were hoping for. Sometimes, these high-risk deals are signed after one incredible season. Other times, they come just as the player is leaving their prime. You know the names: Josh Hamilton, Pablo Sandoval, Chris Davis, etc. But do you remember just how money was shelled out by GMs to sign them? These are the worst MLB contracts of all-time.
Alex Rodriguez, Texas Rangers - $252 Million Over Ten Years
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Sometimes it's not the contract itself that is so bad, it's what it does to the surrounding team. Alex Rodriguez played up to the dollar signs when the Rangers signed him to a historic $252 million, ten-year contract in 2001. The team, however, could barely tread water.
Baseball is a team sport, and the Rangers made it financially impossible to put quality teammates around Rodriguez after blowing the bank with his contract. In the deal's first three seasons, they never won more than 73 games. Before the start of the fourth season, Texas traded their superstar to the New York Yankees.
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Jason Heyward, Chicago Cubs - $184 Million Over Eight Years
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The Chicago Cubs signed Jason Heyward to this monster contract in 2016, hoping he was the missing piece. In some ways he was, but not because of his performance. In his first season, he hit .230 and was considered an instant bust.
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Then, during a weather delay in game seven of the 2016 World Series, Heyward gave the motivational speech of the century, and the Cubs won their first title in over 100 years! Since then his bat has not backed up his words, and Cubs fans are still waiting for the offense they were promised.
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Chris Davis, Baltimore Orioles - $161 Million Over Seven Years
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Chris Davis found a home in Baltimore in 2013 when he hit 53 home runs and knocked in 138 runs. Two years later he put similar numbers, so the Orioles inked him to a seven-year, $161 million deal. Since then, he's only hit over .200 twice and hasn't driven in more than 84 runs.
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If Baltimore had taken Davis' age and strikeout rate into account, they could have seen this decline coming. Instead, the team saw a face of the franchise who led them to the playoffs year after year. In 2017 they missed the playoffs.
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Ryan Howard, Philadelphia Phillies - $125 Million Over Five Years
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Ryan Howard had an incredible career when the Phillies gave him a five-year contract extension in 2010. The $125 million extension officially began in 2012 (it was tacked on the back of his previous contract), and so did his decline.
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Before the 2012 season, Howard had driven in more than 100 runs in six straight seasons. He never did again, coming closest in 2014, his last fully healthy in MLB. Howard retired after the 2016 season, a lost campaign where he hit .196 and played 112 games.
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Pablo Sandoval, Boston Red Sox - $95 Million Over Five Years
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When the Boston Red Sox handed Pablo Sandoval a five-year, $95 million contract in 2015, they thought they were getting a World Series hero. He was only two seasons removed from winning the WS MVP award with the Giants and the contract seemed like a sure bet.
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In his first season on the east coast, Sandoval hit .245 with only 10 home runs. Then he missed most of the next season with a shoulder injury. By 2017, Boston had seen enough and released him with two and half years remaining on his contract.
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Vernon Wells, Toronto Blue Jays - $126 Million Over Seven Years
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From 2002 until 2006, Vernon Wells established himself as one of MLB's most dangerous hitters. The Blue Jays knew they couldn't let him go and signed him to a seven-year contract worth $126 million.
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The next season Wells immediately regressed. His batting average dropped from .303 to .245 and he hit half as many home runs year-over-year. For the last six years of his deal, he was frustratingly inconsistent and was eventually traded to the Anaheim Angels.
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Josh Hamilton, Anaheim Angels - $125 Million Over Five Years
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Josh Hamilton was one of the great comeback stories in MLB when the Angels signed him to a five-year, $125 million contract. The first overall pick by the Tampa Bay Rays in 1999, his career stalled after a struggle with substance abuse.
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When Hamilton got sober, he soared. In 2010 with the Texas Rangers won the American League MVP. In 2013, the Angels won the sweepstakes for the free agent, although they didn't get a good return on their investment and traded him back to the Rangers in 2015.
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Mike Hampton, Colorado Rockies - $80 Million Over Six Years
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It's not easy to pitch at Coors Field. The Mile High Stadium makes any contact off the bat dangerous. As a result, the Colorado Rockies have to overpay for pitching, which they willingly did to sign Mike Hampton in 2001.
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The former Cy Young winner was miserable in Colorado. After two years as a Rockie, his ERA was a ghastly 5.75. The Rockies admitted defeat and traded him to the Braves. In Atlanta, he was better, although an elbow injury ultimately sidelined his career.
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Prince Fielder, Detroit Tigers - $214 Million Over Nine Years
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The son of MLB legend Cecil Fielder, Prince Fielder had a fast rise to stardom with the Milwaukee Brewers. When he hit free agency for the first time in 2012, he was a hot commodity. The Detroit Tigers beat out other suitors with a massive contract worth $214 million.
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With Detroit, he played in 324 straight games and was mostly worth the money. The problem came in 2013 after the Red Sox eliminated the Tigers from the playoffs and he said, "It's not really tough for me. It's over. I've got kids I've got to take care of. I've got things I've got to take care of. For me, it's over, bro." That same fall he was traded to the Texas Rangers.
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Albert Pujols, Anaheim Angels - $240 Million Over Ten Years
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Halfway through his MLB career, most fans thought Albert Pujols would retire a Cardinal. Then he hit free agency in 2012 and joined the Anaheim Angels on a whopping $240 million contract. He was 32-years-old at the time.
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While Pujols was decent for the first few years of his contract, the last two seasons have been awful as he has averaged a .243 batting average. Even worse for the team -- they owe the slugger $30 million each of the next two years of his contract!
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Rusney Castillo, Boston Red Sox - $72.5 Million Over Seven Years
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Rusney Castillo was a high priced free agent acquisition by the Boston Red Sox when he defected from Cuba in 2014. The team handed him a seven-year, $72.5 million deal. With so much money going his way, you would think he would be a staple in the everyday lineup.
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So far, Castillo has failed to make an impact. He has seen limited MLB action and has spent most of his con…

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