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The most memorable players who played for both Red Sox and Yankees

By Gabrielle Starr

HOUSTON, TX - OCTOBER 17: Andrew Benintendi #16 of the Boston Red Sox catches the final out of the game during the ninth inning of game four of the American League Championship Series against the Houston Astros on October 17, 2018 at Minute Maid Park in Houston, Texas. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
HOUSTON, TX - OCTOBER 17: Andrew Benintendi #16 of the Boston Red Sox catches the final out of the game during the ninth inning of game four of the American League Championship Series against the Houston Astros on October 17, 2018 at Minute Maid Park in Houston, Texas. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /
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Johnny Damon
ST. LOUIS – OCTOBER 27: Johnny Damon of the Boston Red Sox celebrates after winning game four of the 2004 World Series against the St. Louis Cardinals at Busch Stadium on October 27, 2004 in St. Louis, Missouri. The Red Sox defeated the Cardinals 3-0 to win their first World Series in 86 years. (Photo by Brad Mangin/MLB Photos via Getty Images) /

Mark Bellhorn

Mark Bellhorn’s midseason switch from the Sox to the Yankees in 2005 was basically the beginning of the end of his career. After helping make history in 2004 with several clutch postseason hits, he struggled so much the following year that the Sox actually released him. He signed with the Yankees soon after, but only appeared in nine games. After a season with the Padres and a few more major and minor-league stints, he officially retired in 2009.

Johnny Damon

For Sox fans growing up in the early 2000s, Johnny Damon’s departure was one of the first great betrayals of our lives. Barely a year after he’d cemented himself as one of the heroes of the 2004 team, he chopped off his flowing Jesus hairdo and signed a four-year, $52M contract with the Evil Empire.

It certainly stung to see Damon in pinstripes. He’s also one of the only players on this list to win a World Series with each time.

Doug Mientkiewicz

Doug Mientkiewicz’s time in Boston was brief, but memorable. For starters, he was acquired in the historic Nomar Garciappara midseason trade. Then, he participated in the greatest comeback in sports history, and became part of the iconic 2004 championship.

After single-season stints with the Mets and Royals, Mientkiewicz spent the 2007 campaign in pinstripes. Unfortunately, it didn’t work out too well for him, as the Sox won the World Series again that year.

Kevin Youkilis

The Greek God of Walks spent the first nine years of his ten-year career in Boston. He was a rookie when they won it all in 2004, and was instrumental to their repeat in 2007, when he won his only Gold Glove award. In the following two seasons, he hit 27+ home runs each year and went to his first two All-Star Games, a feat he’d repeat one last time in 2011.

Unfortunately, when the Sox were going nowhere in 2012, they dealt him to the Chicago White Sox.

Like Mientkiewicz, Youk’s season in the Bronx coincided with a Sox championship; after playing in pinstripes in 2013, he retired. And like Tiant, Youk returned to the Sox in his retirement years. He’s now an analyst on NESN.

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