The end of the most successful era of Cubs history could be coming to a close. 

(click play while reading this to get the full effect)

Theo Epstein signed a 5-year extension with the Cubs in 2016. Anyone who knew anything about the situation told you that Theo would probably move on from the organization after that. That's just how Theo works, he doesn't stay anywhere too long.

Cub fans knew that the core of Theo, Maddon, Bryant, Rizzo, Javy, Schwarber, Contreras, and company wouldn't be around forever and the 2021 season would probably be the last hoorah. Maddon was let go after the 2019 season and reports like this started coming down last week:

It was apparent after not winning a World Series since 2016, this team had too many holes and was getting a little too old to contend for a title for much longer. No one on the team was untouchable and some fan favorites could be wearing different uniforms come 2021.

That's what makes this news a little less surprising than it would have been just a few months ago. Theo was on his way out. Big changes were coming so might as well have the next guy in charge start making the big decisions. That "next guy" will be Jed Hoyer, longtime friend, and partner of Theo's.

Jed is now in charge. The next couple of weeks will most likely bring more big (and possibly bad) news for Cub fans.

Did Theo's time with the Cubs live up to expectations? Depends on who you ask but if you had told me 15 years ago that the Cubs would be sitting here with a World Series trophy and deep playoff run expectations for 5-6 years I would have taken that in a heartbeat.

Thanks for your time here Theo. It might not have ended the way a lot of Cub fans wanted but the ride was better than any in my life as a Cub fan.  Good luck with whatever you do next.