Don Baylor is one of the rare players to be part of a trade between the two rivals.
After three years in the Bronx, they dealt him to the Sox in 1986. He won Silver Slugger awards with both teams, and after the Sox lost in heartbreaking fashion in the 86 Fall Classic, they traded him to the Minnesota Twins the following summer, and with them, he got a ring.
Of all the players on this list, no one spent more time in a Sox uniform than Wade Boggs, who played 1,625 games for Boston between 1982-92. The following year, he departed for the Bronx, where he played the 1993-97 campaigns, finally winning a World Series.
While Boggs’ best offensive years were clearly during his Boston tenure, when he won six Silver Slugger awards in nine seasons, he won his only two Gold Gloves with the Yankees.
Jose Canseco was far more memorable in the early years of his career in Oakland and for being one of the faces of steroids in baseball, but he did spend the 1995-96 seasons slugging 52 homers in Boston and played 37 games for the Yankees in 2000.
Hall of Famer Rickey Henderson spent most of his 25-year career with the Oakland A’s, 14 years in four stints, to be precise. But in between, he spent 596 games for the Yankees and 72 games for the Sox.