A trio of Boston Red Sox signings helped the team capture the 2004 World Series championship and vanquish the “Curse of the Bambino.” Hall of Famers Pedro Martinez and David Ortiz, along with multi-time All-Star Manny Ramirez, led the Red Sox back to prominence. However, not all of Boston’s free-agent acquisitions have proven as successful. Here are the 10 worst free-agent contracts in Red Sox history.
10. Steve Avery: Two years, $8.75 million
The Red Sox signed pitcher Steve Avery to a two-year, $8.75 million contract before the 1997 season. Despite hopes he would recapture his All-Star form from his Atlanta Braves days, Avery struggled in Boston. He appeared in 56 games (41 starts) over two seasons, posting a 5.64 ERA and -0.7 WAR.
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9. J.D. Drew: Five years, $70 million
Outfielder J.D. Drew never lived up to his $70 million contract. Injuries plagued his five seasons in Boston, with significant time missed in 2008 and 2011, his final MLB season. Though Drew won a World Series in 2007 and made an All-Star team, he never achieved the superstar status the franchise expected.
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8. Julio Lugo: Four years, $36 million
The Red Sox gave shortstop Julio Lugo a four-year, $36 million contract before the 2007 season. In return, Lugo committed 42 errors, hit just 10 home runs, and posted a -0.3 WAR. He was designated for assignment in his third season.
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7. John Lackey: Five years, $82.5 million
After signing John Lackey to a five-year, $82.5 million deal before the 2010 season, the Red Sox hoped to get the All-Star pitcher from the Los Angeles Angels. Instead, Lackey posted a 4.46 ERA across 111 starts with a 3.7 WAR before being traded to the St. Louis Cardinals in his fourth season.
6. Daisuke Matsuzaka: Six years, $52 million ($51.1 million posting fee)
The Red Sox invested over $100 million in Daisuke Matsuzaka—a $52 million contract plus a $51.1 million posting fee. While his first two seasons showed promise, including a 2007 World Series victory, injuries later derailed his career. From 2009 to 2012, Matsuzaka made just 55 starts, finishing his six-year Boston tenure with a 4.52 ERA and 9.1 WAR.
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5. Edgar Renteria: Four years, $40 million
Despite signing a four-time All-Star and World Series champion to a four-year, $40 million deal, the Red Sox got just one uncomfortable season from Edgar Renteria. After committing 30 errors, he was traded to the Atlanta Braves.
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4. Hanley Ramirez: Four years, $88 million
Hanley Ramirez’s homecoming — via a four-year, $88 million contract — proved disappointing. He posted two negative WAR seasons and one at just 0.1 before his release in May 2018, during his contract’s final year.
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3. Pablo Sandoval: Five years, $95 million
The same offseason the Red Sox signed Hanley Ramirez, they also inked Pablo Sandoval to a five-year, $95 million contract. Boston struck out on both. Sandoval’s first season produced a .658 OPS, 10 home runs, and -0.5 WAR. Year two saw just three games before season-ending shoulder surgery. The Red Sox designated him for assignment 32 games into his third season, ending his tenure with a .646 OPS, 14 home runs, and -1.6 WAR.
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2. Rusney Castillo: Seven years, $72.5 million
The Red Sox invested seven years and $72.5 million in Castillo, hoping for the next great Cuban star. After signing Castillo in August 2014, he made his debut the next month, hitting two home runs in 10 games. However, Castillo played just 80 games in 2015 (.253/.288/.359, five home runs) and nine games in 2016. He spent the remainder of his contract with Triple-A Pawtucket.
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1. Carl Crawford: Seven years, $142 million
Carl Crawford tops the list of worst Red Sox free-agent signings. His seven-year, $142 million contract yielded just two disappointing seasons. The four-time All-Star hit .255/.289/.405 with only 11 stolen bases in 2011, then played just 31 games in 2012 due to wrist and Tommy John surgeries. The Red Sox traded him to the Dodgers on Aug. 25, 2012, along with Adrian Gonzalez, Josh Beckett, and Nick Punto.
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