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

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.