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3 free agents who won World Series with Red Sox but shouldn’t be re-signed

Gabrielle Starr|
LOS ANGELES, CA - OCTOBER 26: Craig Kimbrel #46 of the Boston Red Sox prepares to deliver the pitch during the ninth inning against the Los Angeles Dodgers in Game Three of the 2018 World Series at Dodger Stadium on October 26, 2018 in Los Angeles, California. (Photo by Harry How/Getty Images)
LOS ANGELES, CA - OCTOBER 26: Craig Kimbrel #46 of the Boston Red Sox prepares to deliver the pitch during the ninth inning against the Los Angeles Dodgers in Game Three of the 2018 World Series at Dodger Stadium on October 26, 2018 in Los Angeles, California. (Photo by Harry How/Getty Images)
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BOSTON, MA – JULY 30: David Price #10 of the Boston Red Sox reacts after making the ground out in the fourth inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA – JULY 30: David Price #10 of the Boston Red Sox reacts after making the ground out in the fourth inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)

David Price

In 2015, the Sox gave David Price the richest pitching contract in MLB history, and he really didn’t live up to it. The 2018 postseason really saved him from being named among the biggest free-agent mistakes in franchise history, a list that includes Carl Crawford and Pablo Sandoval.

Price made his big-league debut with the Tampa Bay Rays in 2008, the same year Chaim Bloom got promoted to Assistant Director of Minor League Operations for the club. During the 2014 season, then-Tigers GM Dave Dombrowski orchestrated a trade to bring Price to Detroit, flipped him to the Toronto Blue Jays the following summer, got fired by the Tigers, and hired by the Sox weeks later. When Price became a free agent following the 2015 season, Dombrowski signed Price to a seven-year deal worth $217M.

Over four years in Boston, Price posted a 3.84 ERA across 103 regular-season games, including 98 starts. In the postseason, he got shellacked by Cleveland in the 2016 ALDS, was only used in relief in the 2017 ALDS, and finally, after a pair of brutal starts in the 2018 ALDS and ALCS, redeemed himself in Game 5 of the ALCS and the World Series.

After the Sox traded him to Los Angeles with Mookie Betts, Price opted out of the 2020 season due to concerns about the pandemic. In the final two years of his contract, he primarily worked out of the bullpen, and posted a 3.47 ERA across 79 games, including 11 starts, 18 games finished, and three saves, all while the Sox paid a hefty portion of his salary.

The Sox got a ring with Price, but overall, it was an underwhelming situation. They just got done paying him to pitch for the Dodgers. Pay him again? No thanks.

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