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

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.