Chapman and Melvin
Bob Melvin, who grew up in the Bay Area, served as the manager of the Oakland A's for eleven seasons (2011-2021). For his final five seasons with the A's, Matt Chapman was his third baseman. Melvin and Chapman both left the A's in 2021: Melvin went on to manage the Padres for two seasons while Chapman played for the Toronto Blue Jays for the same amount of time. In 2024, they returned to the Bay Area to manage/play for the San Francisco Giants. Melvin initially signed a three-year contract with the team, and Chapman later signed a 6-year contract extension.
If Melvin sticks with the Giants for a while, could he and Chapman make history together? Has a manager ever managed a player for at least five seasons with two different teams? I don't know the answer to that question. The closest I could think of was Tony La Russa and Mark McGwire. La Russa was McGwire's manager with the St. Louis Cardinals for 4.5 seasons and his manager with the A's for 9.5 seasons. La Russa managed the late Rickey Henderson when he was on the A's, but did not manage him with another team. Henderson's favorite manager (not La Russa) did manage him for two different teams. Billy Martin managed Henderson on the Yankees (1985 and 1988) and the A's (1980-1982).
What about other sports? The resurgence and dominance of Dallas Cowboys in the early 1990s was due largely to the contributions of Hall of Famers Michael Irvin and Jimmy Johnson. Irvin played for the Cowboys from 1988 to 1999 and Johnson was Irvin's coach for five of those seasons (1989 to 1993). Johnson was also Irvin's coach at the University of Miami for three seasons (1985 to 1987). Johnson was replaced on the Cowboys with Barry Switzer, who was quarterback Troy Aikman's coach at the University of Oklahoma for two seasons. Switzer went on to coach Aikman, Irvin, and the Cowboys for four seasons. While Irvin had a high opinion of Johnson, Aikman did not share a similar view of Switzer.