Conversation so far:
When did Theo Epstein play with the Chicago Cubs?
Theo Epstein was President of the Cubs, not a player.
What position did Theo Epstein play for the Cubs?
Theo Epstein was President of the Cubs.
What did Theo Epstein do as the president of Baseball Operations for the Chicago Cubs?
Theo Epstein turned the Cubs around from having a culture of losing to winning a World Series in 2016.

Question: was he able to do so?
Self-contained rewrite: Was Theo Epstein able to turn the Cubs around?