Theo Epstein has resigned as president of baseball operations with the Cubs, deciding to step away a year before his contract was up. Jed Hoyer and the Cubs are working on an extension, as he’ll replace Epstein as the top person on the baseball side of things.

Prior to the news of Epstein’s departure, he wrote a letter to the Cubs and his colleagues explaining his decision. The Athletic was able to get a copy of the note and you can read it all here.

Theo’s decision to leave

To start off, Theo was leaving the Cubs no matter what, as he once again referenced Bill Walsh’s 10-year time frame of staying in the same place.

I think most of you know that I have always planned to be with the Cubs for a maximum of ten years. Bill Walsh’s theory that in the sports industry a change in leadership after about a decade can be beneficial for both the organization and the individual has always resonated with me. The idea is that the executive finds the renewed vigor and passion and creativity that comes with a new challenge; the organization receives the jolt of a fresh perspective and the chance for immediate growth that comes with change

However, this decision to leave has been in the works for a few years, as he and Cubs owner Tom Ricketts had been communicating about the transition to the next president of baseball operations since the middle of 2020.

Tom and I had been communicating for the last couple years about how to execute a transition that leaves the Cubs in the best possible position going forward. While we had been operating with the basic assumption that the formal transition would take place next October, this summer it became apparent to me that for a number of reasons we should consider moving the timeframe up a year.

Short-term challenges for Cubs

Before we go on, and I hate being the party pooper here, but things were already looking bleak for the Cubs this offseason. We’ve seen the reports about the Cubs not figuring to be players in free agency, not even at the second tier of players let alone the top free agents. Yet, we also started to hear the rumblings of potentially cutting players simply to slash more payroll.

So yeah, that means the possibility of non-tendering guys like Kyle Schwarber or even Kris Bryant just to save money might be on the table this offseason.

Aug 11, 2017; Phoenix, AZ, USA; Chicago Cubs infielder Kris Bryant (17), infielder Anthony Rizzo (44), outfielder Ian Happ (8) and infielder Javier Baez (9) celebrate after closing out the MLB game against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Jennifer Stewart-USA TODAY Sports

And let’s just say that this following passage from Theo’s letter doesn’t really paint a pretty picture for this offseason.

First, the organization faces many decisions this winter that carry long-term consequences; those types of decisions are best made by someone who will be here for a long period rather than for just one more year. Second, as we know all too well, COVID-19 has brought serious threats and impacts to our business and our people — and to every sports franchise in the country — and we must face the immediate challenge of how to allocate our temporarily reduced resources in a way that allows us to move forward and to succeed. In a way my presence in 2021 would actually make that challenge more difficult.

Again, the Cubs will probably make a few more big moves that drastically shape the future of the roster.

What’s next for Theo?

Theo Epstein can probably do whatever he wants right now. Politics? Another baseball job? Own a team? Go to a different sport? Literally anything, but as far as 2021 goes, Theo said he’s taking the year off to spend time with his family and help non-profit organizations.

For starters, I’m looking forward to working with a few non-profits: The Foundation To Be Named Later in Chicago and Boston, the CASE (Careers As Sports Executives) Study Program here at the Cubs, and The Players Alliance as a member of its Executive Advisory Committee.

And no, Theo didn’t leave the Cubs to immediately go to a different organization. Also, yes, he would be interested in ownership down the road.

I do plan on having a third chapter leading a baseball organization someday, though I do not expect it to be next year. 
If and when the timing and opportunity and partners are right, I would like to join an ownership group. In the meantime, I would love to find a way to serve the game that has given me so much and am pursuing a few possible avenues to do just that.

Yet, that doesn’t mean teams aren’t going to call Theo all winter long.

Well, farewell Theo. Thanks for everything. It was an awesome time.