As Theo Epstein Departs, What Will Become of the Cubs?

After nine seasons, three division titles, a pennant and an historic World Series championship, Theo Epstein is saying goodbye to the Cubs. That surprising news came Tuesday afternoon, announced jointly by the team and its outgoing president of baseball operations. “I believe this is the right decision for me even if it’s a difficult one,” Epstein wrote in a statement released to the press. “And now is the right time.” Chicago will now be under the control of Jed Hoyer, the team’s general manager and Epstein’s long-time second in command, but the fate of both the franchise and its departing boss is less clear.

Taking over the Cubs in October 2011 after leaving the Red Sox under a cloud (and disguised as a gorilla), Epstein helped transform Chicago from National League also-ran and frequent cellar dweller into a juggernaut, culminating in the 2016 World Series win that ended a century-long title drought. He and his lieutenants drafted, developed or acquired virtually every important piece of that ‘16 roster, from Kris Bryant to Anthony Rizzo to Kyle Schwarber to Jon Lester to Jake Arrieta, and set the stage for what looked to be a dynasty. But diminishing returns and short postseason stays have left the Cubs in the championship cold over the last four seasons, and now their architect is moving on.

Those recent struggles may be part of Epstein’s decision to leave, though in a letter he sent to team employees and acquired by The Athletic, he claims that a decade at the helm was all he had in mind from the start. “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,” Epstein writes. Those of you blessed with the gift of being able to do basic math will note that 2020 minus 2011 equals nine, not 10. But per Epstein’s letter, a number of factors came into cutting his reign short by a year, including the COVID-19 pandemic and its impact on the team’s finances; the presence of Hoyer, who joined the club as GM when Epstein arrived; and, as Epstein put it, “decisions this winter that carry long-term consequences … best made by someone who will be here for a long period.”

Translation: Ahead of what’s expected to be a chilly offseason across the league and looking at a weakened club that’s getting increasingly older and potentially more expensive, Epstein decided he didn’t have the appetite for the changes coming in Chicago. And that’s understandable, given how things have played out on the North Side since 2016. While the core of that team remains in place, the performance of its key pieces has fluctuated wildly. On top of that, the Cubs have mostly stayed out of free agency, save a nine-figure outlay for Yu Darvish, while the farm system has produced only fitfully. The result has been a roster oddly full of holes for a team with the resources that Chicago has, and one that hasn’t reached the World Series since that ‘16 campaign or the NLCS since ‘17. Its last two forays into October have been downright Hobbesian in their quickness and brutality: a Wild Card game loss to punchless Colorado (after blowing a 3 1/2-game lead in the NL Central over Milwaukee with 11 games to go and losing the division in a tiebreaker) in ‘18, and a Wild Card Series loss to the upstart Marlins this fall. Those sandwiched a third-place finish in ‘19.

That disappointing 2019 cost Joe Maddon his job just three years after he hoisted a trophy and prompted a spate of “Are the Cubs finished?” pieces (including by yours truly). The 2020 results under new skipper David Ross — a 34–26 record and a division title — suggested we’d written our obituaries too soon, but the Cubs seemed more paper tiger than real contender, as Miami made that plain by sweeping them out of the playoffs at an empty Wrigley Field. A peek under the hood showed plenty of problems: down years across the lineup; a thin rotation beyond Darvish and Kyle Hendricks; a bullpen that was allergic to holding leads; and a general sense that what had been one of the most forward-thinking organizations in the game was now spinning its wheels and stuck in the mud, unable to find a path forward.

Add that all up, and it’s no surprise to see Epstein using words like “transition” and “challenges” in his departing missive. The window for this Cubs team is closing quickly, if it hasn’t already shut, and the tasks facing the brain trust this winter alone are substantial. Bryant, Schwarber and Javier Báez are all entering their final year of team control, and Bryant in particular has become an issue without easy resolution after he filed and lost a grievance against the club for delaying his call-up and gaming his service time; a trade this offseason feels more likely than not. Rizzo will return via a $16.5 million team option, but he turns 32 in August and is unlikely to be around or as productive past 2021. Darvish and Hendricks top the rotation, but there isn’t much depth behind them. Even beyond whatever additions need to be made, simply keeping the band together won’t be cheap, with raises due through arbitration for Bryant, Báez, Schwarber, Willson Contreras and Ian Happ and $66 million still owed to Jason Heyward over the next three years. The farm system won’t be much help in keeping costs down or plugging holes: Eric Longenhagen ranked Chicago 24th in the majors ahead of the 2020 season, and while both Brailyn Marquez and Adbert Alzolay showed promise in brief major league stints, there’s not much else coming down the pike at the moment.

If nothing else, the talent on hand remains strong (assuming it remains), but the problem in Chicago is twofold. First is figuring out why this particular team is less than the sum of its parts, and why its most important players — namely Báez and Bryant — struggled so badly in 2020. Second is the fact that ownership has displayed no real interest in spending what it takes to make the Cubs better. Since handing Darvish a $126 million contract ahead of the 2018 season, the money faucet has turned off. Despite a need for one or both, Chicago sat out the Manny Machado and Bryce Harper sweepstakes; the team’s lone major league signing that offseason was Daniel Descalso. Last winter was more of the same, as the Cubs tinkered around the margins with reclamation projects like Jeremy Jeffress and Jason Kipnis instead of splashing around in the deep end of the free-agent pool.

It’s a bizarre mindset for a franchise and ownership group each worth billions, but the Ricketts family is apparently more content to throw its dollars at political campaigns and PACs than at the lineup or bullpen. (The Ricketts have spent plenty on improvements to Wrigley Field and on surrounding real estate ventures, but that has as much to do with increasing the value of the team and the stadium and thus netting more money from its fans as it does with the players on the field, and even there they’ve complained loudly about the local government not chipping in more.) Like every other club, the Cubs have embraced fully the desire to avoid the luxury tax and to shrink payroll, and the pandemic’s economic after-effects will only lead to a further tightening of the belt. At a time when the team should be spending the money it has to lock up its homegrown stars and try to extend its contention cycle with impact free agents, you can bet that the Ricketts will once again cry poverty. That puts a hard cap on just how much Chicago can improve or avoid falling apart, and sets the stage instead for retrenchment both financially and in the standings.

With that in mind, it makes sense that Epstein decided that 2020 was it for him — or at least, will mark his end in Chicago. In his letter to the team, he wrote that he has no plans on working in baseball next year and that his ultimate goal is to join the ranks of the owners. That tracks for the man who took the Red Sox and Cubs to the promised land; once you’ve climbed Mt. Everest and K2, what else is left? Whether that promise holds true given plum leadership opportunities with the Mets and Phillies is an open question, and I expect one or both of those teams, particularly newly deep-pocketed New York, will try to change Epstein’s mind with as much money as possible. (It’s worth noting that, in leaving the Cubs, he’s forgoing the $10 million salary he would’ve earned next season.) Maybe they’ll succeed, but it’s just as likely that Epstein sticks to his word and tries to join the next group of hedge-fund moguls and ex-athletes trying to buy a franchise — one that would almost certainly be thrilled to have his name attached to their bid.

Still just 46 years old, Epstein’s future is bright. Can the same be said about the Cubs as he leaves them? “I am excited about the Cubs’ future despite the obvious short-term challenges,” he wrote in his letter. Hopefully for Chicago, that’s not just a parting pleasantry as he walks out the door.