Tony La Russa drove Brewers fans crazy for decades, but his track record is nothing short of incredible. In all, 5,097 regular season games managed. He has 2,728 wins, third all-time in baseball history, and a mere 35 wins away from second-place John McGraw. He is only one of two coaches/managers to have been at the helm for more than 5,000 games in any North American professional sport. Connie Mack, who both owned and managed the Philadelphia Athletics for 50 seasons, is the only other.