There are some Chicago Cubs who are doomed to be gone by the 2021 season.
The Chicago Cubs appear to be at the end of the best run in the history of the organization. They have made the playoffs in five of the past six years under Theo Epstein but with their current situation, the window seems to be closing. Theo’s contract is up after 2021 and there is a very low chance that he returns after that. He likes to take on new challenges every ten years and this would be the end of his current run if he sticks to that word.