Theo Epstein might be done with the Cubs after 2021.
Theo Epstein is just 46 years old, and he already has almost two decades of decision-making experience as a GM or president of baseball operations in the MLB. While he has spent the last decade with the Chicago Cubs, having turned the laughingstock into a perennial playoff team, there is reason to believe 2021 will be Epstein’s final year in Chicago.
“I’ve been transparent about my feeling that after a certain period of time there can be real benefit for both an individual leader and an organization for some change,” Epstein said. “I’m not going to run away from those feelings but I’m also as invested in the Chicago Cubs as I was at any point in the last nine years.”
Theo Epstein saved the Chicago Cubs by building a young, sustainable roster
Epstein has broken baseball’s two most notable World Series droughts, as he helped the Boston Red Sox win their first title in 86 years during the 2004 season. After winning again in 2007 and seeing a roster that was heavily influenced by his decision making win again in 2013, Epstein took the job as president of baseball operations in Chicago.
Epstein emphasized acquiring young talent and rebuilding their farm system. The frit of that labor showed up in the selection of Kris Bryant in the draft, the development of Javier Baez, and the trade for Anthony Rizzo. After also hitting several home runs in free agency by signing the likes of Jon Lester, Epstein helped the Cubs win their first championship in 108 years when they took down the Cleveland Indians in 2016.
Even if Epstein doesn’t stay with the Cubs, and his exit might come at a time in which Chicago hasn’t had as much playoff success as they did in the middle part of the decade, his ingenious moves helped the Cubs win their first title in 108 seasons, and he’ll forever remain a huge part of Cubs lore for his role in assembling the 2016 curse-breaking squad.