Five Worst Free Agent Signings in Red Sox History

The Boston Red Sox spend money. Boston wants to beat New York at everything, and they are one of the franchises that is financially set enough to stand toe to toe in a free agency battle. But taking chances can sometimes fail miserably. Let’s take a look at the five worst free agent signings in Boston Red Sox history.


Steve Avery had been a key part of the Atlanta Braves pitching success in the early 90s. But he was never the same after an injury in September 1993. Avery became a free agent in 1997, and the Red Sox signed him to a two year, $8.75 million dollar deal. Avery became the highest paid pitcher in Boston and the second highest paid player on the roster after Mo Vaughn. Unfortunately for Boston, Avery was cooked. He won just 16 games with a 5.61 ERA in his two years in Boston.

Boston Red SOx
Pitcher Steve Avery #33 of the Atlanta Braves winds up for the pitch during game four of the NLCS against the Cincinnati Reds at Fulton Stadium in Atlanta, Georgia. The Braves defeated the Reds 6-0.. Mandatory Credit: Rick Stewart /Allsport


The Red Sox often struggled at the shortstop position, and Lugo is the perfect example of a bad shortstop signing in Boston. General Manager Theo Epstein handed Lugo a four-year $36 million deal to sign with the Red Sox. It was a failed attempt to replace defensive wizard Alex Gonzalez. Lugo committed 42 errors while in Boston posting a negative WAR in two of his three seasons. Offensively, he hit just .251 with a .664 OPS. Boston eventually cut its losses, designating him for assignment in July 2009 with Epstein describing the contract as “a sunk cost.”

Boston Red SOx
Boston, MA – 5/7/09 -Red Sox/Indians – Julio Lugo is congratulated by Mike Lowell after crossing home in first after hitting lead off triple to start game. (Globe staff photo/ Bill Greene)


The crazy international posting exacerbated this signing for Boston. The Red Sox posted $51.1 million just for the right to sign Daisuke to a six-year $52 million deal. What? I understand it has something to do with international signings, but that’s just crazy to pay that just to have a chance to sign him for more money before he takes the field.

From there, Matsuzaka’s first two years were solid and he contributed to Boston’s 2007 World Series title. For some Red Sox fans, that would be enough to keep him off this list, but after 2008, things got ugly. Over the final four years of his contract, Matsuzaka only started 34 games, posting an 11-14 record with a 5.53 ERA. He also ended up undergoing Tommy John surgery and missing the equivalent of a full season.

Boston Red Sox
Boston, MA, USA; Boston Red Sox starting pitcher Daisuke Matsuzaka (18) throws a pitch as they take on the Miami Marlins in the third inning at Fenway Park. Mandatory Credit: David Butler II-US PRESSWIRE


What can I say about Carl Crawford that hasn’t been said? Crawford terrorized Boston for years while playing in Tampa. The Red Sox decided the best way to keep Crawford from destroying them was to sign him to destroy others. Crawford signed a seven year, $142 million deal, and it was the equivalent of highway robbery. His signing did exactly what they wanted to avoid. It destroyed the Red Sox.

Crawford started the 2011 very slow before getting injured. He kept trying to get on the field in 2012 but he just didn’t have it. In late 2012, before two seasons of his contract were done, Boston gave up on Crawford trading him, Adrian Gonzalez, Josh Beckett and Nick Punto to Los Angeles for Ivan De Jesus Jr., Rubby De La Rosa, James Loney, Jerry Sands and Allen Webster. In all, Crawford played in 161 games, one less than a full season, and posting a paltry .260 batting average with 23 stolen bases and 126 strikeouts.

Boston Red Sox
08-01-11 Boston, MA: The Red Sox Carl Crawford has a big amile, and he brought smiles to the fans faces as well as he comes into the dugout following his third inning solo home run. The Boton Red Sox hosted the Cleveland Indians in an MLB regular season game at Fenway Park. (Globe Staff Photo/Jim Davis)


At least Carl Crawford tore the cover off the ball against the Red Sox making them think it would be good to sign him. The same can’t be said for Pablo Sandoval. Kung Fu Panda played great in postseasons with the Giants. He won three championships and a World Series MVP award, mostly for hitting three home runs in Game 1 of the 2012 World Series. He made two All Star teams, but no one considered him worthy of a five-year, $95 million contract when Boston gave him that deal. Boston signing Hanley Ramirez, who was better offensively and played the same position defensively, at the same time made this more peculiar.

In his first year in Boston, Sandoval set career-lows in batting average, OPS, home runs and RBIs with a negative WAR. He played three games in his second season before undergoing season ending shoulder surgery. Boston designated Sandoval for assignment after just 32 games in the 2017 season. He was released with $48 million remaining on his contract. While the issues with Carl Crawford and Steve Avery were injury related, Sandoval’s struggles were mostly self-inflicted. Critics focused on his conditioning during his entire tenure in Boston. Both in production and attitude, he’s my pick for worst free agent signing in Red Sox history, if not all of Boston sports history.

Boston Red Sox
Boston-04/05/2017- Boston Red Sox vs Pirates- Sox Pablo Sandoval reacts after striking out in the 5th inning with runners on bases. John Tlumacki/Globe staff

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