You can’t write an article about MLB ejections without mentioning John McGraw. After 1900, he remained the all-time leader in ejections (137) for over 100 years until he was finally passed by Bobby Cox in 2007. For over 50 of those years, no other person even reached 100 ejections until Leo Durocher reached that milestone in 1955. Still today McGraw, Cox, and Durocher are the only people to be thrown out of an MLB game over 100 times.
John McGraw, known as “Little Napoleon” and “Muggsy” among other nicknames, managed in the MLB for 33 seasons starting in 1899 and ending in 1932. Over this time his teams made it to the World Series 10 times and won it 3 times. His overall winning percentage as a manager was .586.

Here is an interactive timeline of MLB ejections (player and manager combined) *data from Retrosheet:
Connie Mack:
He managed in 7,755 games and played in 724 games but was ejected just once in his 61 years playing/managing in the MLB. The 15 other people who managed over 3,500 games had at least 25 ejections each. His 7,755 games managed is a record by far with the next closest manager (Tony La Russa) over 2,500 games away still.

Bobby Cox:
Bobby Cox is the all-time leader in ejections with 165.

Future members of the 100 Ejection club:
Active Managers with over 50 ejections:
There are only 2 active managers with over 50 ejections: Tony La Russa and Joe Maddon.
- Tony La Russa has 91 ejections as of today and is the manager of the White Sox. He by far has the best chance of joining the 100 ejection club of active managers.
- Joe Maddon has 60 and is the manager of the Angels. He has an outside change of reaching the 100 ejection milestone, but is 20 ejections away from getting in the top 10 all-time.
Managers who managed as recent as 2010 that have 50 or more ejections:
- Ron Gardenhire has 85, ranking him 7th all-time, but he announced his retirement in 2020.

- Joe Torre has 84, ranking him 8th all-time, but last managed in 2010.
- Lou Piniella has 78, ranking him 11th all-time but last managed in 2010

- Bruce Bochy has 77, ranking him 12th all-time, but last managed in 2019

- Jim Leyland has 73, ranking him 13th all-time, but last managed in 2013
