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

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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ST. LOUIS, MO – SEPTEMBER 6: Relief pitcher Andrew Miller #21 of the St. Louis Cardinals pitches in the sixth inning against the Los Angeles Dodgers at Busch Stadium on September 6, 2019 in St. Louis, Missouri. (Photo by Michael B. Thomas /Getty Images) /

Andrew Miller

Andrew Miller’s tenure in Boston got off to a rocky start. The Sox actually non-tendered him less than a month after acquiring him, but then re-signed him days later.

His struggles in the starting rotation and injury in 2012 prompted the Sox to move him to the bullpen, a role in which he thrived. However, injuries continued to limit him, and the Sox traded him to the Orioles at the 2014 deadline for Eduardo Rodriguez. After pitching excellently in Baltimore, the Yankees swooped in and gave him a four-year contract ahead of the 2015 season.

Adam Ottavino

Adam Ottavino mostly makes this list because he famously bragged that he could strike out Babe Ruth.

Ottavino is also rare trade between the Sox and Yanks, only the second deal since 1987.

Andrew Benintendi

After playing on several Red Sox postseason teams, including their 2018 championship squad, Andrew Benintendi is now a Yankee.

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