Mark Buehrle(amongst other current players) played with Harold Baines for the White Sox in 2001, who played with Minnie Minoso for the White Sox in 1980, who played with Al Benton for the Indians in 1949, who played for Connie Mack with the A's in 1934, who made his debut in 1886.
Or we can look at this in reverse order. Connie Mack debuted in 1886, managed Nellie Fox in 1949, who played with Joe Morgan in 1964, who played with Chili Davis in 1982, who played for the 1999 Yankees with a bunch of current players.
It could also take another route in '64, Fox and Morgan also played with Staub who played with Strawberry for the Mets as late as '85, who also played on the '99 Yankees.
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