5 worst free-agent contracts in Boston Red Sox history

NEW YORK, NY - AUGUST 6: Pablo Sandoval #48 of the Boston Red Sox in action against of the New York Yankees in the first inning during a MLB baseball game at Yankee Stadium on August 6, 2015 in the Bronx borough of New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - AUGUST 6: Pablo Sandoval #48 of the Boston Red Sox in action against of the New York Yankees in the first inning during a MLB baseball game at Yankee Stadium on August 6, 2015 in the Bronx borough of New York City. (Photo by Rich Schultz/Getty Images)
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Red Sox OF Carl Crawford
BOSTON, MA – JULY 16: Carl Crawford #13 of the Boston Red Sox reacts against the Chicago White Sox at Fenway Park July 16, 2012 in Boston, Massachusetts. (Photo by J Rogash/Getty Images)

Crawford couldn’t handle the pressure of playing for the Red Sox

Carl Crawford spent the first nine years of his career terrorizing the Red Sox as a member of the Tampa Bay Rays. Signing the four-time All-Star to a seven-year, $142 million deal was as much about taking away from a division rival as it was adding to their own roster. He can’t do damage to our club if he’s one of us, right?

They couldn’t have been more wrong. Crawford did plenty of damage with his underwhelming production on the field and with his attitude in the clubhouse.

Crawford set a career-low with a .255 batting average during his first season in Boston while his .694 OPS was the lowest he produced since his first full season in the big leagues.

Speed was always a vital part of Crawford’s game. He swiped 46+ bases in seven of his first eight full seasons, topping 50 steals four times and reaching 60 once. Crawford stole only 18 bags for the Red Sox in 2011.

Crawford was once viewed as a strong defensive outfielder who earned a Gold Glove in 2010 but as soon as he arrived in Boston, he immediately became below-average with -1 defensive runs saved.

An epic September collapse by the Red Sox was sealed by Robert Andino’s walk-off base hit against Jonathan Papelbon in the final game of the regular season. Crawford made a half-hearted slide that came up short on the line drive to left and followed with an off-target throw that failed to beat the runner scoring the game-winning run. It would have been a great play if Crawford had made the catch but it still felt like he misplayed it, costing his team a trip to the postseason.

Crawford never seemed comfortable in Boston and many questioned if he could handle the pressure of playing in a big market after thriving for the small-market Rays. He became a malcontent who contributed to a toxic clubhouse environment that eventually forced the Red Sox to make a drastic roster overhaul.

In August of 2012, the Red Sox made a blockbuster trade with the Dodgers to send Crawford, Josh Beckett, Adrian Gonzalez and Nick Punto to Los Angeles. Gonzalez was the target for the Dodgers but the Red Sox insisted that they take Crawford and Beckett off their hands, removing their bloated contracts from the payroll and their poor attitudes from the clubhouse.

The financial freedom created by the trade enabled the Red Sox to rebuild their roster in 2013 around high-character veterans, leading to an improbable worst-to-first turnaround and a World Series title.

About a year and a half of disappointing production isn’t what you expect when you sign a free-agent to a contract that, at the time, was the highest average annual value in franchise history. Boston got lucky that the Dodgers were wiling to take their salary dump, even if it cost them their All-Star first baseman.

Celebrating a championship in 2013 washed away much of the bitterness from the dysfunctional Red Sox teams that preceded that magical season but we’ll never completely be able to forget about the expensive mistake that Crawford turned out to be.

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