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10 Worst Boston Red Sox Free-Agent Contracts Of All-Time, Including Several All-Stars

Pablo Sandoval, Boston Red Sox
Credit: Eric Hartline-Imagn Images

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

Steve Avery, Boston Red Sox
Credit: RVR Photos-Imagn Images

9. J.D. Drew: Five years, $70 million

J.D. Drew, Boston Red Sox
Credit: David Butler II-Imagn Images

8. Julio Lugo: Four years, $36 million

Julio Lugo, Boston Red Sox
Credit: Kirby Lee-Imagn Images

7. John Lackey: Five years, $82.5 million

John Lackey, Boston Red Sox
Credit: Kim Klement-Imagn Images

6. Daisuke Matsuzaka: Six years, $52 million ($51.1 million posting fee)

Daisuke Matsuzaka, Boston Red Sox
Credit: Brad Penner-Imagn Images

5. Edgar Renteria: Four years, $40 million

Edgar Renteria, Boston Red Sox
Credit: John Rieger-Imagn Images

4. Hanley Ramirez: Four years, $88 million

Hanley Ramirez, Boston Red Sox
Credit: Kevin Jairaj-Imagn Images

3. Pablo Sandoval: Five years, $95 million

Pablo Sandoval, Boston Red Sox
Credit: Bill Streicher-Imagn Images

2. Rusney Castillo: Seven years, $72.5 million

Rusney Castillo, Boston Red Sox
Credit: Douglas DeFelice-Imagn Images

1. Carl Crawford: Seven years, $142 million

Carl Crawford, Boston Red Sox
Credit: Joy R. Absalon-Imagn Images
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