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

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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Andrew Benintendi
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.

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