What's next for the Cubs following Theo Epstein's sudden departure?

Mark Townsend
·Yahoo Sports Contributor
·5 min read

Theo Epstein shook up the baseball world Tuesday, announcing he would step down as Chicago Cubs president of baseball operations effective Friday.

Epstein, 46, walks away one year before his Cubs contract was set to expire. He was the architect behind the Boston Red Sox World Series titles in 2004 — which ended an 86-year drought — and again in 2007. When he joined the Cubs front office in 2011, he oversaw a complete rebuild that culminated with a World Series title in 2016, ending Chicago's 108-year drought.

With his legacy as a front office executive secure, Epstein will now embark on the next chapter of his baseball journey. There's already plenty of speculation regarding what that move will be. If he elects to pursue another front office position, he will be atop every team’s wish list.

From the Cubs’ perspective, Epstein’s departure comes at a pivotal time. His right-hand man, general manager Jed Hoyer, will take over as Chicago’s primary decision-maker at a time when several very important decisions have to be made. It’s possible Epstein’s early departure gives us some indication of what lies ahead in Chicago. While another complete rebuild isn’t likely, it’s even less likely Chicago will keep its core in place. Most notably, Kris Bryant, Anthony Rizzo, Javy Báez and Kyle Schwarber won’t all be around beyond the 2021 season, as they are all set to become free agents.

Now the question is: Who among them will stay, and who among them will go?

Those are some of the decisions Hoyer must weigh. Another might be whether now is the time to move on from Yu Darvish, coming off his runner-up finish in NL Cy Young voting. Here now, we'll examine the potential moves on the horizon for Hoyer this winter, and how they might shape the Cubs moving forward.

After Theo Epstein's departure, what does the future hold for Kris Bryant and Yu Darvish in Chicago? (Photo by Nick Wosika/Icon Sportswire via Getty Images)
After Theo Epstein's departure, what does the future hold for Kris Bryant and Yu Darvish in Chicago? (Photo by Nick Wosika/Icon Sportswire via Getty Images)

Will the Cubs trade or non-tender Kris Bryant?

Could you imagine a 28-year-old former MVP not being tendered a contract? It sounds impossible, but it's something budget-tightening team ownership may force Hoyer to consider.

Like every other team in MLB, the Cubs say they lost millions during the pandemic-shortened season. Even before that, they were acting like a team determined to trim payroll. As a result, they will almost certainly be aiming to shed salary this winter, rather than adding on. That means someone from the core four of Bryant, Rizzo, Báez and Schwarber might have to go this winter, and the most likely option from that group right now is Bryant.

It's interesting, too. The Cubs spent most of Bryant's tenure fighting for an extra year of control after he filed a service-time grievance stemming from his 2015 call-up. The Cubs ultimately won the case, meaning Bryant’s free agency was delayed from this winter until next. Now it’s possible, if not likely, the Cubs will exhaust every option to avoid paying Bryant a hefty salary in 2021, even if that means not tendering him a contract and letting him walk for free.

Of course, the Cubs will first attempt to trade him. They shopped him around last winter, but the pending grievance prevented any potential deals from gaining traction. The problem is they could be without leverage this winter too because of Bryant's injury-riddled 2020 season and other teams’ awareness of the chance they won’t tender him a contract by the Dec. 2 deadline, thus making Bryant a free agent anyway.

Short of Bryant signing a team-friendly extension, which given the history here is very unlikely, it feels like the Cubs can’t win here. The only upside might be using any money saved on Bryant to re-sign Rizzo or Báez. Though again, if the Cubs are dead set on shedding payroll, there’s no guarantee that money would be immediately reinvested.

Is it time to trade Yu Darvish?

While the Cubs stand to lose on the Bryant front, they could profit this winter by trading Yu Darvish.

The 34-year-old right-hander’s value won’t get any higher after he finished runner-up in NL Cy Young Award voting. In 76 innings, Darvish posted a career-best 2.01 ERA while striking out 93 batters and only walking 14.

Most notably, Darvish finally looked healthy. After signing a six-year, $126 million deal before the 2018 season, he spent most of his first two seasons in Chicago battling injuries and ineffectiveness. In 2020, Chicago got the version of Darvish they expected all along. However, given his age, history and their purported financial situation, the Cubs still might not be eager to pay the $59 million he’s still owed through the 2023 season.

Darvish rehabbing his value was good news for Chicago. The real game changer might be Darvish’s contract. It’s reported that Darvish's deal included a full no-trade clause through the 2020 season, but it becomes a limited no-trade clause for the final three seasons. That opens up some opportunities that might make sense for Chicago to pursue, even if Darvish isn’t keen on leaving.

If the Cubs do trade Darvish, that would leave Kyle Hendricks and Alec Mills as the only two regular starters under team control for 2021. Jon Lester, Jose Quintana, and Tyler Chatwood are all currently free agents. The rotation would need a near complete overhaul, but if going younger and cheaper is the Cubs’ goal this offseason, trading Darvish for some prospects would help accomplish it.

If there’s one thing we can take away from Tuesday’s announcement, it’s that Epstein sees the writing on the wall. If the Cubs core is destined to be broken up, then winning another championship will become a distant dream.

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