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

How many players in MLB history have played for both the Boston Red Sox and New York Yankees?

When the New York Yankees acquired former Boston Red Sox star Andrew Benintendi from the Kansas City Royals ahead of the trade deadline, he became the 236th player in MLB history to play for both teams in baseball’s biggest rivalry.

On Friday, Benintendi will return to Boston for the first time since the Sox traded him to the Royals.

Ahead of the three-game series between the two scuffling rivals, take a look back at some of the most memorable players who wore both uniforms:

Charlie Hemphill

Charlie Hemphill was the first Red Sox player to also play for the Yankees. He joined the Sox for their inaugural season in 1901 and played 136 games for them that year.

Unfortunately, Hemphill arrived in Boston with a less-than-stellar reputation; the Boston Globe called him “the poorest outfielder in the league.” After a brief stint in Cleveland and five years with the St. Louis Browns (now the Baltimore Orioles), Hemphill finished out his career playing four seasons with the Yankees. In 1912, he transitioned into the role of player-manager in the minor leagues, but when he got drunk and didn’t report for a game, he was fired and his contract was sold to another team.

Jack Chesbro

Jack Chesbro was one of the great pitchers of the early 1900s, twice leading the league in games started. In 1904, his MLB-leading 55 games pitched included 48 complete games and a grand total of 454 2/3 innings. It would’ve been a guaranteed Cy Young Award season, but the award wouldn’t exist for another half-century; Young himself was pitching for the Red Sox at the time.

Unlike most of the players on this list who left Boston for New York, Chesbro went from the Yankees to the Sox in 1909. The future Hall of Famer made exactly one start for the Red Sox before retiring.