Baseball contracts put organizations in quite the gambling mood, risking millions on player potential. As salary structures grew from the reserve clause era to today’s nine-figure commitments, some deals crashed spectacularly. Here’s a look at MLB’s most problematic contracts.
Baseball contracts work just as marriage vows do – thrilling when signed, but sometimes that initial excitement fades quickly. You’re stuck with years of commitment and no easy way out. Remember Ross and Rachel’s exhausting relationship limbo in “Friends”? These contracts left fans similarly wondering if their team’s expensive promise would ever deliver the goods.
Mike Hampton (2001 Rockies)
Mike Hampton signed an eight-year, $121 million contract with the Colorado Rockies in December 2000. Adjusted for inflation, this deal would fetch approximately $190 million today. He lasted just two seasons with the Rockies, starting 62 games with a disappointing 5.75 ERA. Hampton tallied only 0.3 WAR total, with -1.6 WAR from pitching somewhat offset by 1.9 WAR with his bat.
Hampton arrived in Colorado after a stellar 2000 season with the Mets. His pitching skills and rare hitting ability enticed a Rockies franchise desperate for pitching success at mile-high Coors Field. Hampton’s skills failed to adjust to Denver’s thin air, resembling a perfect piano that suddenly goes out of tune when moved to a different climate. His strikeout rate dropped while walks increased. The Rockies couldn’t help Hampton adapt to altitude, highlighting major flaws in their development approach.
Albert Belle (1999 Orioles)
Albert Belle signed a five-year, $65 million contract with the Baltimore Orioles in 1999. This ranked as MLB’s largest contract then, worth about $135.1 million in current dollars. Belle hit 37 home runs with a .941 OPS his first season but recorded a terrible -3.3 defensive WAR. His career ended after just two seasons due to hip problems.
Belle joined Baltimore during owner Peter Angelos’ aggressive spending spree. Coming off eight straight 30+ homer seasons, Belle seemed a perfect offensive weapon for a team trying to compete in the expensive AL East. Hip osteoarthritis forced Belle’s early retirement, leaving three years and roughly $39 million on his contract. Insurance paid about 70% of his remaining salary, but the Orioles essentially burned $11.7 million on a player who never took the field again.
Prince Fielder (2012 Tigers)
Prince Fielder signed a nine-year, $214 million contract with Detroit in 2012, about $237 million in today’s money. He delivered a solid 4.7 WAR in 2012 before declining performance prompted a trade to Texas. Fielder suffered career-ending neck problems, forcing retirement in 2015. Oddly enough, he became MLB’s highest-paid player in 2020 despite being retired five years.
Detroit signed Fielder after losing Victor Martinez to injury, creating a fearsome duo with Miguel Cabrera. His left-handed power seemed tailor-made for Comerica Park. Fielder’s body betrayed his talents too soon, similar to how a smartphone sometimes dies right after the warranty expires. After trading him to Texas for Ian Kinsler, the Tigers remained on the hook for $30 million. His injury triggered insurance payments that helped Texas, but the Rangers still took a massive financial hit.
Josh Hamilton (2013 Angels)
Josh Hamilton signed a five-year, $125 million deal with the Angels in 2013. He appeared in merely 240 games over two seasons, hitting just 31 total home runs. The Angels traded him back to Texas in 2015 while covering most of his remaining salary. What a bargain.
Hamilton joined the Angels after five remarkable seasons with the Rangers, including an MVP award. The Angels, having already paid for Albert Pujols, saw Hamilton as their championship puzzle’s final piece. Hamilton’s career trajectory mirrored a Hollywood blockbuster that bombs at the box office despite an all-star cast. His substance abuse issues complicated matters throughout his Angels tenure. His performance tanked, with his OPS falling from .930 with Texas to a pedestrian .741 in Anaheim.
Carl Crawford (2011 Red Sox)
Carl Crawford signed a seven-year, $142 million contract with Boston in 2011, roughly $159.7 million today. Crawford joined Boston after an exceptional 7.0 WAR season with Tampa Bay. Injuries and poor performance got him shipped to Los Angeles after barely 1.5 seasons.
Crawford arrived in Boston as baseball’s Swiss Army knife, offering speed (47 stolen bases in 2010), respectable power, and stellar defense. His signing highlighted Boston’s rebuilding strategy after missing the playoffs. Crawford’s relationship with Boston turned sour faster than yesterday’s milk. He never adapted to Boston’s intense media pressure or his contract’s expectations. Wrist and elbow injuries sidelined him repeatedly. His 2011 season produced 0.0 WAR – essentially a league-minimum player earning superstar money.
Chris Davis (2016 Orioles)
Chris Davis signed a seven-year, $161 million contract with the Baltimore Orioles in 2016. He later set a major league record with 49 consecutive hitless at-bats in 2019. Davis batted .168 in 2018, the lowest average for any qualified hitter in MLB history. Knee issues ended his 2020 season, and he retired in 2021.
Davis secured his massive payday after leading MLB with 47 home runs in 2015 and 53 in 2013. Baltimore, having lost Nelson Cruz and others, felt pressured to keep their remaining offensive star despite warning signs. His performance collapsed immediately after signing, resembling an expensive fireworks show where nothing actually explodes. His batting average plummeted while strikeout rates soared. By 2018, his negative WAR made him among baseball’s least valuable players, yet his untradeable contract kept him in Baltimore.
Ryan Howard (2012 Phillies)
Ryan Howard signed a five-year, $125 million extension with Philadelphia in 2012, about $147 million today. He suffered a devastating Achilles tear during the 2011 playoffs. Howard never reached 25 home runs or 100 RBIs again after signing.
Howard’s extension rewarded his contributions to Philadelphia’s golden era, including their 2008 World Series win and five straight division titles. From 2006-2011, he averaged 44 home runs and 133 RBIs per full season. The Achilles injury wrecked Howard’s mobility and power, comparable to a star restaurant suddenly losing its best chef and trying to maintain quality with lesser talent. His batting average against lefties cratered, turning him into a platoon player earning elite money. Philadelphia’s mistake compounded as they kept playing him despite obvious decline.
