Fansided

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

By 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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Should the Red Sox try to reunite with any of their 2018 World Series champions in free agency?

In October, Pedro Martinez cautioned the Boston Red Sox that losing key players would destroy the culture he, David Ortiz, and other legends of the early aughts worked so hard to cultivate and pass down to the players who came after them.

He spoke, of course, about Xander Bogaerts and Rafael Devers. Bogaerts opted out, and Devers is in his final year of arbitration. Whether the Sox can get their act together and lock them both in long-term will make or break the next decade of Boston baseball.

Bogaerts and Devers are key to Boston’s future success because of their proven history of winning together. Bogaerts first helped the Sox win the championship when he was only 20 years old in 2013. In Devers’ first two years in the majors, the Sox won the American League East in back-to-back seasons and the 2018 World Series. In 2021, they bucked all expectations and took the Sox from unexpected Wild Card team to Game 6 of the ALCS. Like most rational people, Martinez wants them in Boston to keep this level of success going.

Those two aside, though, the Sox should be looking forward, not back. Chaim Bloom shouldn’t be trying to resurrect the 2018 team, but he might be able to build a new contender if ownership wises up and lets him.

Here are three former champs the Sox shouldn’t be looking at on the free-agent market this winter…

Yes, Craig Kimbrel completed over 40 saves in 2018. He was also so unreliable that year that Alex Cora famously relied upon his starting pitchers – and a miraculous catch from Andrew Benintendi – to close postseason games.

The Sox let Kimbrel walk after the World Series, and he held out for months into the 2019 season until the Chicago Cubs gave him the bloated contract he still felt he deserved after a down year by his standards. Last summer, they traded him across town to the Chicago White Sox, who promptly messed with the first good season he’d had in years, by making him the setup man to the closer they already had, Liam Hendriks.

Oct 17, 2018; Houston, TX, USA; Boston Red Sox left fielder Andrew Benintendi (16) makes a game ending diving catch during the ninth inning against the Houston Astros in game four of the 2018 ALCS playoff baseball series at Minute Maid Park. Mandatory Credit: John Glaser-USA TODAY Sports
Oct 17, 2018; Houston, TX, USA; Boston Red Sox left fielder Andrew Benintendi (16) makes a game ending diving catch during the ninth inning against the Houston Astros in game four of the 2018 ALCS playoff baseball series at Minute Maid Park. Mandatory Credit: John Glaser-USA TODAY Sports /

Should the Red Sox re-sign Andrew Benintendi?

Andrew Benintendi fell apart when Alex Cora moved him to the leadoff spot in 2019 and by 2020, he looked so lost that every time he moved from the on-deck circle to the batter’s box, he looked like he was being led to the guillotine.

Between his big-league debut in 2016 and 2018, he hit .282/.359/.447 with 78 doubles, 38 home runs, 151 walks, and 243 strikeouts over 333 regular-season games. Over 152 games between 2019-20, he hit .255/.341/.410 with 41 doubles, 13 home runs, 70 walks, and 157 strikeouts.

After the Sox traded him to the Royals ahead of the 2021 season, he found himself again. He won his first career Gold Glove award in 2021 and was an All-Star this summer before the Royals traded him to the Yankees.

Since leaving Boston, Benintendi has lowered his strikeout rate and gotten back to drawing walks, but his home-run power still hasn’t returned; he only hit five round-trippers in 126 games this year. He’s only reached 20 home runs once in his career, in his first full season back in 2017.

But there’s no guarantee that a return to the place where he struggled so much would do anything but undo all the progress he’s made. Benintendi thrived in Kansas City because it was a lower-pressure environment; getting traded to the Yankees at the deadline, he struggled under the harsh spotlight. After hitting .320 with a .387 OBP in 93 games with the Royals, he hit .254 with a .331 OBP over 33 games with the Yankees. Whereas he collected 111 hits and only struck out 52 times before the trade, he only managed 29 hits and struck out 25 times after.

Ultimately, the 4-year, $56M contract he’s projected to receive this offseason is far too much to gamble on someone who struggled so much here not too long ago.

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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