Some came close to leading the Chicago Cubs to the promised land but until Theo Epstein was hired no one did what needed to be done.
The Cubs were the punch line of jokes, they were the Loveable Losers, some believed they were cursed by the owner of a bar with a barnyard animal or by a random stray black cat. They were certainly affected by absentee owners, some poor front office operations and lousy field managers.
They are no longer the Lovable Losers and there is a reason for that. That reason announced his departure from the organization this week and it is time to look back beyond the Theo Epstein era and realize how profoundly he changed the trajectory of the Chicago Cubs.
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The Cubs have had eight owners in the 108 years between World Series wins. They have had fifteen Presidents in that same period before Theo Epstein and didn’t have a General Manager until 1934 and there were fourteen of them leading up to Jed Hoyer.
From 1981 to 2008 only Dallas Green and Jim Hendry managed to put together anything close to a winning organization. While they account for almost all of the Cubs’ six playoff appearances since 1984, they never got the team to World Series.
Tom Ricketts bought the Cubs in 2009 and by 2011 he’d seen and spent enough. The 2011 Cubs were in very deep trouble. The 71-91 team had the sixth-highest payroll in all of MLB, a core of aging veterans, and a few toxic personalities. The farm system was a disaster, the scouting department was being outmaneuvered, Wrigley Field was falling apart and their Dominican facility was even worse. It was so bad Tom Ricketts fired Hendry before the season’s end.
Talk of an Epstein to Cubs move began almost immediately that late summer of 2011 and spiked when he was seen at a Chicago Starbucks on October 8. The deal was clinched on October 21, 2011. Jed Hoyer and Jason McLeod followed soon after.
A teardown/rebuild began immediately, encompassing every aspect of the franchise. From the farm system, scouting department, front office operations and MLB bench, nearly everything would be changed and nearly everyone would be gone. This effort, described by ESPN in 2014, is likely the most massive undertaking in professional sports franchise history.
The rest we know. A magical 2015 playoff run followed by a dream season with a spectacular World Series win in 2016. But it’s the seasons since then that tells us how different it is. It’s no longer “Wait ’til next year” and that’s a huge difference from where we have always been. Theo Epstein did that, too.