Elston Howard
Eight years after Jackie Robinson broke MLB’s color barrier, the Yankees made catcher Elston Howard their first Black player in 1955. By 1963, he was the first Black player to win the American League MVP, and by the time the Yankees traded him to the Sox in 1967, he had 12 All-Star Games, four World Series rings and two Gold Glove awards under his belt.
Upon the Sox releasing him in October 1968, Howard returned to the Bronx as the first Black coach in the AL, and worked on two more championship teams.
Jackie Jensen
Jackie Jensen’s 170 home runs with the Red Sox are the most by a player who also played for the Yankees. He spent the 1950-52 seasons in the Bronx but was far more successful once he shipped up to Boston in 1954.
George Scott
Before Wade Boggs stepped on the scene, George Scott was the longest-tenured Red Sox player to also play for the Yankees. After 1,192 games with the Sox from 1966-79, the eight-time Gold Glove-winner played 44 games for the Royals and 16 games for the Yankees in the final season of his career.
Luis Tiant
Should-be Hall of Famer Luis Tiant was one of the first Red Sox players to depart for the Yankees in free agency in 1978. After Curt Flood fought for his right to not be a Philadelphia Phillie in 1969, Catfish Hunter, Dave McNally, and Andy Messersmith became the first true free agents in 1974-75.
A few years later, the collapse of the reserve clause and the new world of free agency meant that Tiant could
However, in retirement, El Tiante returned home to Boston, where he remains a beloved part of the fabric of Fenway. His Cuban sandwich shop is a fixture on Jersey Street, and fans will often find him sitting there, ready to chat and sign autographs.
In other words, after sampling both teams, he chose the better one.