Chicago Cubs: Will the window of contention close in 2021?

The Chicago Cubs went from ‘Loveable Losers’ to World Series champions in just two years. Theo Epstein has built a roster capable of sustainable success, but all good things must come to an end eventually, so when will the Cubs’ window of contention close?

It’s no secret that the Chicago Cubs have built a sustainable core of All-Star caliber talent around the diamond. With the likes of Anthony Rizzo, Kris Bryant, Willson Contreras, Addison Russell (to name just a few), the Cubs are in prime position to contend for not only the NL Central, but the National League pennant from this point forward for many years to come. But just how long is the window of opportunity open?

First of all, let me preface this by saying when a team lead by an outside-the-box thinker such as Theo Epstein, anything is possible. Anything.

There’s a clear window of contention, and when you look at the contract situations of the Cubs young core, you’ll notice that the winter of 2021 is going to be especially painful.

Why do I say that? How about this: Anthony Rizzo has two team options built into his contract that are available for 2020 and 2021. After that, he hits the open market.

Decisions will have to be made

Kris Bryant, Addison Russell, Javier Baez and Kyle Schwarber will all be hitting free agency as well during that winter after multiple cycles of arbitration.

If these players continue to produce at the level they have been (and in the case of Russell, Baez and Schwarber, even continue to develop), it’s going to be very, very difficult to keep everyone around. When/if the time comes for the core to go their separate ways, I might cry. No, I will cry.

Breathe. There is still plenty of time to sort everything out. Knowing Epstein, he already has the next five years planned out on how to keep the Cubs in contention.

However, I think it’s important that we start to be realistic about the status of the team on how it affects the future of the franchise. Maybe it’s time we prepare ourselves for the inevitable deconstruction of the legendary Cubs team that broke the 108-year curse.

The next chapter?

As I previously said, anything and everything is possible with Epstein and the rest of the Cubs front office, but there is a chance (a very real chance) that Epstein decides to move on from the Cubs after the 2021 season when his contract expires to revitalize another franchise and break another “curse.”

In the meantime, Epstein means business. With the window of contention stretching from 2018-2021, he’ll be busy putting the best team on the field he can. As it stands now, the Cubs are on the hook for $149.7M in 2018. That number takes a nosedive in 2021 ($86.1M) as a big chunk of the roster will be off the books by then.

Obviously, the moves leading up to that point need to be accounted for, but should the Cubs somehow attract Bryce Harper (as the industry is beginning to anticipate) in free agency next year, say goodbye to at least $35M a year for the length of his contract. That number could quickly reach $40-45M depending on how his market develops.