Chicago Cubs: What if Theo Epstein leaves the front office?

Just one year after the Boston Red Sox won the World Series, GM Theo Epstein resigned because of a dispute over authority with the Red Sox CEO. Could he do the same to the Chicago Cubs?

Just a year after the Boston Red Sox won the 2004 World Series and shook the burden of the Curse of the Bambino, General Manager Theo Epstein resigned from his duties in Beantown unexpectedly.

Though he would eventually return a few weeks before spring training commenced, Theo was undoubtedly frustrated with working under what the Boston Globe described as the “heavy hand” of President & CEO Larry Lucchino.

Red Sox superstar David Ortiz even went on record to question who was going to succeed Epstein, saying “If you’re going to be the GM, just to get orders from someone else, it’s something they aren’t really comfortable with.”

That doesn’t sound too reassuring, given that it seems as if Epstein was given a bag of quarters to work with in free agency this offseason.

Chicago Cubs CEO Tom Ricketts told the media at the beginning of spring training that the team had “no money to spend.”

I’m sorry…what?

Has anyone seen $2 billion laying around? The Ricketts family seems to have misplaced it.

Then again, perhaps the family actually is on a spending limit. As a recent Deadspin article explained, the Ricketts family took on far more debt than the MLB CBA allows, and that debt could grow by another $225 million pending the outcome of an upcoming trial on the team’s sale and the possibility of the Tribune Company’s indemnity clause being invoked.

One truly has to wonder if Epstein would want to continue his tenure with the Cubs under an ownership group that could find themselves in far more debt than expected and thus unwilling to spend big money on the team.

Even potential debt aside, why would the Ricketts want to spend more money that they may or may not have? Especially considering that they claim that they’ve already accomplished their three goals to “be good neighbors to the city of Chicago; preserve Wrigley Field for future generations and win a World Series”?

The Cubs virtually made no big moves over the offseason, despite a collapse of epic proportions at the end of 2018 and an early Wild Card exit. Many fans are left wondering why the club was so stagnant over the winter.

What if Epstein’s hands are tied by the Ricketts family?

Epstein’s resume speaks for itself. He’s in it to win championships, not save money. He doesn’t care about names or fame. He cares about analytics and who gives the team the best shot to win.

In no world do the analytics of the Cubs performance from last season suggest that the team is a championship contender this year.

Perhaps the Cubs ownership better pony up some cash in the coming winters or risk losing Epstein to the next championship-starved organization.

Or perhaps Theo just likes breaking hearts and curses. Or maybe he’s on the North Side to stay.

It must be stressed that this is simply a thought of what COULD happen given history and some of the recent developments (or lack thereof) in the Cubs executive decisions. Though there haven’t been any rumors of any discord or potential change, we know for certain that Epstein doesn’t like limitations or subordination.

Hopefully we’re wrong and Epstein remains with the Cubs and brings more championships to the North Side. Until we find out more about the Cubs plan in the coming months, we can only speculate.