2. Harry Wolverton
Harry Sterling Wolverton played in MLB between 1898 and 1905 for multiple teams, and in 1912 as a player-manager for the New York Highlanders, the precursor to the New York Yankees. During the early years of MLB, it was not unusual for individuals to be a player and a manager at the same time.
“Fighting Harry” replaced Hal Chase as player-manager and led the Highlanders to a last-place finish and a dismal 50-102 record (a .329 winning percentage). (He sometimes inserted himself in games as a pinch hitter, and he batted .300 during the season.)
He often fought with club owners over the low salaries his players received, which created a lot of tension on the team. He was let go by owner Frank Farrell after the conclusion of the 1912 season because of his behavior and poor performance as the Highlander’s skipper. Subsequent managerial stints led to similar outcomes.