Connie Mack - 3731 wins
Manager with the most wins is Connie Mack with 3731 career wins.
Connie started his managerial career in 1894 as player-manager in Pittsburg Pirates. After three seasons with the Pirates as a player-manager, he retired in 1896.
Mack has the record for not only the most wins but for the most losses (3948) and most games managed (7755)) as well. Connie's career is filled with accolades.
He is the first manager to win consecutive World Series twice. He finished his career with nine AL pennants and nine World Series appearances.
Tony La Russa - 2902 wins
The second manager with the most wins in MLB is Tony La Russa with 2902. He is behind Torre in the manager with the most playoff wins with 70.
He surpassed the John McGraw record on 6th June 2021 becoming the second-winningest manager in MLB.
The Athletics Hall of Famer started his managerial career with the White Sox followed by Athletics in the 1986 season.
In his 33 years as a manager, he has guided his teams to three World Series titles, six League Championships, and 13 Divison titles.
Also, LA Russa has won the Manager of the Year award four times in his career.
He took A’s to a 1989 World Series title and 3 ALCS from 1988 to 1990. Tony announced his retirement from managing duties on 3rd October 2022 with the White Sox.
John McGraw - 2763 wins
McGraw remains third in the rankings behind La Russa and Mack with 2763 wins.
John has served almost 30 years as a manager for the New York Giants and third baseman for the Orioles known for their attacking gameplay.
He is widely known as one of baseball's greatest managers, holding the record for most seasons managed in NL, 31.
McGraw also won the ten pennants during his time with the Giants exerting control on players. His 10 pennants being a manager was matched only by Casey Stengel.
Bobby Cox - 2504 wins
Bobby Cox started his managerial career with the Braves in 1978. He left for the Blue Jays in 1982 and returned after four seasons.
Cox has won the World Series both as a coach and manager. He was the coach of the 1977 World Series champion Yankees. His second World Series title came in 1995 with the Braves.
Cox ranks third in the winningest playoff manager with 67 postseason wins.
Throughout his career, he recorded six 100-win seasons, a record only matched by Joe McCarthy. Cox was named the "Manager of the Year" for four seasons and has won five pennants.
Joe Torre - 2326 wins
MLB manager with most postseason wins is Joe Torre with 84.
He is the only person in MLB to hit 2,000 hits as a player and win 2,000 games as a manager.
He also ranked fifth position in the manager list with the most career wins with 2326. He is the only Major League personnel to achieve both 2,000 hits as a player and 2,000 victories as a manager.
When he was a Yankees manager from 1996 to 2007, he led the team to six American League pennants and four World Series titles.
Torre has set an MLB record for guiding his clubs to 14 Consecutive World Series wins from Game 3 of 1996 WS through Game 2 of 2000 WS.
Among the 84 playoff wins, he has won most with the Yankees with 76 with other remaining 8 with the Los Angeles Dodgers in 2008 and 2009.
In his six final appearances in World Series as a manager with the Yankees, he has won four of them and lost two in 2001 and 2003.
Joe has nine All-Star selections as a player and a Golden Glove award in his name.
Sparky Anderson - 2194 wins
Sparky Anderson is among the managers to win pennants in both the league with the Reds and the Tigers.
He is also ranked sixth in the list of managers to have 2,000 career wins with 2194. He won the NL Championships in 1975 and 1976 followed by the third championship with Tigers in American League in 1984.
He was awarded the AL Manager of the Year in 1984 and 1987 and is counted among the sixth most winningest manager of all time in MLB history.
Dusty Baker - 2170 wins
Dusty Baker is the latest addition to the list after his 2022 World Series victory with the Astros. He has a total of 2170 career wins as of 5th September 2023.
With a total of 4022 games managed in his managerial career, he has maintained a winning percentage of .540 to date.
As far as winning the pennants in both leagues, he is among the managers to win pennants in both leagues. In 2002, he won the NL pennant with the Giants and won the World Series with the AL team Astros in 2022.
Buckey Harris - 2150 wins
Ranked in the list of managers with 2000 wins, Harris has an altogether career wins of 2150 games.
Buckey was hired by the Senators in 1927 and led the team to the 1924 World Series title. He became the youngest manager to win the title and the first rookie manager to claim it.
He has managed over 29 seasons as a manager counted as the fourth longest-tenured manager in MLB with five teams.
Harris won three league pennants and two World Series with the Senators and 1947 with the New York Yankees. He had a winning percentage of .493.
Joe McCarthy - 2125 wins
McCarthy is the first MLB manager to win pennants in both leagues. He won his NL pennants with the Cubs in 1929 and his AL pennant with the Yankees three years later.
He has won a total of nine league pennants and seven World Series Championships in his managerial career. Joe also has recorded a 100-win season six times which is matched by the only manager Bobby Cox.
Bruce Bochy - 2076 wins
Bruce Bochy is on the list of managers with above 2,000 wins and also the fifth manager to have the most post-season wins with 42.
He managed the Padres for 12 seasons till 2006, SF Giants for 13 seasons as a manager totalling to 25 years as a manager.
He led the Giants to 3 World Series titles and the Padres to one World Series appearance. He is ranked 11th on the list to achieve 2000 wins. He has a total of 2076 wins as of 31st August 2023.