Here's one from the Oracle of Baseball that connects the manager of my oldest team collection (T205) to one of my most recent player collections.
John McGraw played with Roger Bresnahan for the 1901 Baltimore Orioles. (There isn't a card of Bresnahan with Baltimore, but there is this one of them both that came later.)
Roger Bresnahan played with Bob O'Farrell for the 1915 Chicago Cubs
Bob O'Farrell played with Phil Cavarretta for the 1934 Chicago Cubs
Phil Cavarretta played with Minnie Minoso for the 1954 Chicago White Sox
Minnie Minoso played with Harold Baines for the 1980 Chicago White Sox
Harold Baines played with Jim Thome for the 1999 Cleveland Indians
Jim Thome played with Brian Matusz for the 2012 Baltimore Orioles