Closing Time: Why Theo Left the Cubs and What's Next For Chicago

Cubs fans knew it was on the horizon, but the announcement that Theo Epstein would be immediately stepping down as president of baseball operations still came as a shock. Instead of fulfilling the last season of his second five-year contract, Epstein opted to hand over the reins to his right-hand man Jed Hoyer during a crucial offseason for the franchises' future.

In his time with the Cubs, Epstein accomplished practically everything he set out to in his introductory press conference. Completely retooling a broken farm system and talent evaluation process, building a perennial contender, three straight NLCS appearances, and of course, bringing a long-awaited World Series title to the North Side of Chicago.

With those results in mind, anyone trying to claim Epstein was anything but the perfect man for the Cubs is simply firing up the hot take machine. Still, it's impossible to bask in the glory of 2015-2017 without mentioning the regression and playoff failures of 2018-2020. The core couldn't hit, the bullpen collapsed, free-agent signings started to miss, and the October well simply ran dry. So, why did Theo leave and what is next for a franchise at a turning point?

Why Theo Left

A casual outsider may assume that Epstein left due to the team's recent inability to reach expectations. While that certainly may have contributed, Theo has always been clear about his "10-year policy" as dictated by Bill Walsh. In hisgoodbye letter to the organization, he laid out the philosophy behind this mindset.

"I think most of you know that I have always planned to be with the Cubs for a maximum of ten years. Bill Walsh's theory that in the sports industry a change in leadership after about a decade can be beneficial for both the organization and the individual has always resonated with me."

"The idea is that the executive finds the renewed vigor and passion and creativity that comes with a new challenge; the organization receives the jolt of a fresh perspective and the chance for immediate growth that comes with change."

Epstein views himself as more of a builder than a maintainer. He embraces an organization down on its luck and is excited by the opportunity to bring in change and a fresh perspective. As everyone knows, this process led to him breaking two historic curses in Boston and Chicago.

But in both instances, after achieving that ultimate goal he didn't stick around for long. With the Red Sox, he first resigned after the 2005 seasonciting the fact he could"no longer put his whole heart and soul into it."He then escaped out of Fenway Park in a gorilla suit on Halloween.

While he eventually returned to the Sox from 2006-2011 (winning another title in 2007), it's clear that Epstein is motivated by building a contender not sustaining dominance. The 2011 Red Sox suffered an epic late-season collapse, losing 18 of their final 24 games and getting the boot from postseason play on the last day of the season. This is why he took the Cubs job in the first place, and ultimately the reason he has now left it.

"If you look at my track record in Boston and then here, in the first six years or so we did some pretty epic things, and then the last couple years weren't as impressive,"Epstein said in his final press conference.

"Maybe what that tells me is I'm great at and really enjoy building and transformation and triumphing. Maybe I'm not as good and not as motivated by maintenance so to speak, and as soon as you get to the point where it can start to feel that way to you then I think you owe it to yourself and as importantly, if not more importantly, to your employer to be open about that."

For fans, it's undoubtedly disappointing to hear that the savior of the franchise is leaving at a time he is needed most. But if Epstein isn't motivated in the way he used to be, it's hard to see things working out well anyway.

In addition to that overarching mentality, the realities of the Cubs franchise moving forward made this an appropriate window for change. Knowing he didn't plan to stick around any longer than 2021, Epstein didn't see why he should be the one making long term decisions.

"First, the organization faces many decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than for just one more year,"Epstein wrote in his letter.

"Second, as we know all too well, COVID-19 has brought serious threats and impacts to our business and our people -- and to every sports franchise in the country -- and we must face the immediate challenge of how to allocate our temporarily reduced resources in a way that allows us to move forward and to succeed. In a way, my presence in 2021 would actually make that challenge more difficult."

What exactly is Theo talking about? Well, basically every recognizable player on the Cubs is at or on the cusp of free agency. The team declined to pick up Jon Lester's option this offseason, instead paying a $10 million buyout of his contract. Pitchers Tyler Chatwood, Jeremy Jeffress, and Jose Quintana are now free agents. 2020 additions Cameron Maybin and Jason Kipnis are gone.

Core players Anthony Rizzo, Kris Bryant, Javier Báez, and Kyle Schwarber will all be free agents after the 2021 season and 2x All-Star catcher Willson Contreras' contract expires after the 2022 campaign. The few threads of continuity lie in Yu Darvish, Ian Happ, Jason Heyward, and the always underrated Kyle Hendricks (each of which is under team control through 2023).

*Craig Kimbrel is also with the club through 2023, but he hasn't exactly proven himself to be consistently reliable in the back of the bullpen.

Big decisions are about to be made regarding who this roster will be comprised of going forward. One thing is for certain, these guys are not all staying. Jed Hoyer will need to take a serious look in the mirror and figure out who is worth paying, who should be traded this offseason, and who will walk after 2021.

Add in the financial crunch and uncertainty of COVID-19 and you have the makings of a huge turning point in Cubs history. Theo is right that he shouldn't be the guy making these calls if he doesn't plan to stick around.

What's Next

I can't tell you what decisions will be made in the coming months but I can tell you Jed Hoyer is the right guy to make them.

Hoyer has high-level experience with the Red Sox, Padres, and Cubs and was crucial in bringing key World Series players like Anthony Rizzo and Pedro Strop to Chicago. Keep in mind that Pedro Strop had a 7.25 ERA in 2013 with Baltimore and quickly became one of the best relievers in Cubs' history.

Theo gets credited (or blamed) for the many transactions on his watch. One where it was Jed Hoyer "pounding the table" was when he insisted on Cubs getting Pedro Strop as part of the Arrieta-Feldman/Clevenger trade with the Orioles.-- Jordan Bastian (@MLBastian)November 17, 2020

Theo gets credited (or blamed) for the many transactions on his watch. One where it was Jed Hoyer "pounding the table" was when he insisted on Cubs getting Pedro Strop as part of the Arrieta-Feldman/Clevenger trade with the Orioles.

A primary criticism of Epstein over the years was that he grew too attached to the guys he drafted. Instead of flipping someone like Kyle Schwarber or Kris Bryant at the peak of their value, he opted to trust what he had built. Hindsight is always 20/20 and it's hard to blame Theo for the shocking production drop-off of many Cubs players, but a well-timed trade could have uplifted the franchise.

Instead of moving pieces in the name of maintenance, Epstein stuck with what got him there in the first place. This approach ultimately led to failure as the same problems kept reappearing.

After the 2018 season, in which the Cubs collapsed in September, Epstein famously stated that the offense "broke". He then did very little to change that offense and watched it struggle to come through when needed most in 2019 and 2020.

Theo Epstein: "The Cubs' offense broke sometime in 2018."Cubs' response: Well, we'll just hope all the dudes who broke in 2018 improve instead of spending money to get Harper or Machado. Fans: Oh okay cool I'm excited to spend lots of money on tickets to see this in person.-- Spencer (@sbp_21)December 11, 2018

Theo Epstein: "The Cubs' offense broke sometime in 2018."Cubs' response: Well, we'll just hope all the dudes who broke in 2018 improve instead of spending money to get Harper or Machado. Fans: Oh okay cool I'm excited to spend lots of money on tickets to see this in person.

With so many big decisions looming, installing a new leader who may be more open to shaking things up seems like a positive. If the Cubs want to exit this time of tumult as contenders, they are going to need creative thinking and the strength to let go.

On the North Side, the long imagined glory years have been quickly followed with a painful restructuring. The current front office shuffle is a product of the encroaching dramatic roster change. While seeing Theo leave is painful, it just might be the only way this team stays relevant in the near future.