21. 3,731 Career Wins as a Manager
Team/Player: Connie Mack
Mack certainly helped his case for this record by managing until he was 85 years old, but there's also no denying that he benefitted from having pretty soft competition for much of his tenure as well. Managing almost exclusively in the pre-integration era while African-Americans flourished in the Negro Leagues, Mack kept amassing victories without being forced to go against the best competition available. He also enjoyed phenomenal job security; in addition to managing the Philadelphia Athletics, he also owned the team. We don't rule out this also happening with Jerry Jones in the near future.