Now I Really Know How Theo Epstein Feels

Several months ago, I wrote a piece that detailed a very odd dream I’d had. In it, I struggled with paying my tab at a small watering hole and, upon waking, I determined that the frustration I had experienced must be akin to that of the Cubs head baseball honcho.

At least, that’s what I thought at the time. Little did I realize that events would conspire to prove me wrong. You see, all I had been focused on at the time of that earlier post was the frustration and the minutiae of the situation, never a good vantage point.

But now I’ve zoomed from microscope to telescope and, while still reeling from the rapid change in POV, I think I’ve got a better handle on what Mr. Epstein must have felt in coming to Chicago, what he still feels now as he sees the results of his handiwork manifest themselves on the diamond.

Because inasmuch as we look at a man who has been given millions upon millions of dollars, both in personal salary and team payroll, he’s also someone who took a great risk. Theo Epstein didn’t have to come to Chicago at all; he could have stayed in Boston, could have found a softer landing spot with another, better equipped franchise.

Heck, he could have walked away from baseball altogether and done part-time consulting work while sitting on a nice stack of his Red Sox money. But he chose to start over, to rebuild a moribund franchise from the ashes of an ill-fated puppet empire.

Okay, perhaps the latter part of that is too harsh. But the Cubs had spent the better part of the first decade of the 21st century placating fans by pumping a lot of money into the team, covering up bad investments like a renter spackling nail holes with toothpaste.

But that would have been the safe play, the easy play. Everyone was happy, the beer was flowing like wine, and fans flocked to Wrigley like the salmon of Capistrano. But with a change in ownership, a keystone card was pulled out, and the flimsy house fluttered to the floor in a hurry.

Theo Epstein, along with Jed Hoyer, was very clear about how the whole process was going to go down. He told everyone that it wasn’t going to be easy and he did it behind a facade of confident GM-speak that surely belied his true feelings.

Beneath the calm demeanor, I have no doubt that Epstein has felt a great deal of frustration, anxiety, and outright fear at the prospect of starting over from scratch and trying to rebuild something from what was seemingly a bunch of disparate parts. But as time has gone on, it looks as though his vision is being realized.

I think I speak for Tom Loxas as well when I say that that’s exactly how we feel here at Cubs Insider. We had a really nice setup at ChicagoNow and they provided us with a great deal of support and an amazing platform from which to reach a wide audience.

Still, something pulled at us, a force that was stronger than reason. Both of us felt the need to build something of our own in order to fully realize our shared vision. So, fueled by creative energy and a lot of IPA, we set about creating what you see now at

We want to bring you the same quality content you have seen from us in the past, but we also want to be able to adapt and customize our site to continue to best serve our readers. We’ve got a very strong core group of staff members and contributors and we want to grow this thing just like the team we follow.

Getting this started has been frustrating at times. It’s been scary. I know we’re anxious about it. But it’s also incredibly exciting and fulfilling to see things coming together and to see the fruits of our labor coming to maturity. I think this is what Epstein must feel like as he watches Javier Baez launch a home run after striking out two or three times.

But none of this would have been possible without our readers, and we’re going to need your help to get Cubs Insider off the ground. Please sign up to receive updates, share links via social media, and give us your feedback. One of our reasons for making this move was to give you more of what you want, so this site should be one that you enjoy visiting.

Thank you so much for being here, we think it’s gonna be a hell of a ride!


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