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.