Complex sentence: Ferguson's last two managerial positions were in the American Association, when he was player-manager for the Pittsburg Alleghenys, who later became the Pittsburgh Pirates, in and later took over the managerial role for parts of two seasons with the New York Metropolitans.
Split into simpler sentences: Ferguson's last two managerial positions were in the American Association. He was player-manager for the Pittsburgh Alleghenys, who later became the Pittsburgh Pirates, in and later took over the managerial role for parts of two seasons with the New York Metropolitans.