At his personal charity event in Boston Monday night, Chicago Cubs President of Baseball Operations Theo Epstein discussed a wide range of things, most notably the outstanding compensation issue.

But Epstein also spoke at length about his first offseason with the Cubs, and about the process of building – not rebuilding – a long-term winner.

Among his notable thoughts, together with some reactions:

  • On the Cubs’ successful offseason: “You never accomplish everything that you want to. We wanted to get younger, we wanted to get a little more athletic, we really wanted to bolster the starting-pitching depth, which was fairly non-existent. We wanted to get better defensively, we wanted to get a little bit more left-handed, we wanted to convert some short-term assets to long-term assets, we wanted to acquire some prospects along the way. To varying degrees, we were able to accomplish all those things.” It’s not as if Epstein is creating a set of plans after the fact, contorting them to match what the organization did. These were, indeed, the tasks he and Jed set out to accomplish back in November. I think they’ve done a good job.

  • On “building” versus “rebuilding,” and the future in Chicago: “I don’t agree with the word ‘rebuilding’ ever. Because, for one thing, it denotes that you’re building something that already existed, but that’s not how baseball works. You’re constantly growing and moving onto the next iteration of the club, so I think building is the appropriate [word] – sure we’re building in Chicago, but we went through some building phases here. The art of it is trying to do it in a way where nobody notices. When you’re winning 95 games a year and getting into the playoffs, then people don’t notice that we’ve integrated a lot of this talent and we’ve made a lot of short-term sacrifices for long-term stability. I think there were a lot of times when we were able to pull that off here [in Boston], there were a lot of times that we failed as well.” I don’t agree with Epstein’s refusal to use the word, “rebuilding,” but, hey, Epstein is a lawyer, and lawyers are wont to beef about certain words because of the particularities they associate with that word (if you use “disinterested” around me, and you use it incorrectly, I will bite you). What matters is the message, and, with that, I agree.
  • On the difference between being in a small market and a large market, and how it impacts your strategy: “At some point, there’s sort of a lot of pressure to have big names or to win every single year, which is not part of the small-market mentality. It’s usually more of a building effort …. It’s more of a balancing, a need to take a small step back to ensure a better long-term future. You fight that fight for a while in a big market, I think when you’re at your best, you fight it successfully ….┬áSometimes the sheer force of being a big market kind of takes over. But, it is what it is. There are tremendous resources that come with being a big market, there’s also potential pitfalls. I think every small market would trade places for the opportunities that come with more resources.” What can I say? That’s the perfect attitude – think like a small market club, but avail yourself of the benefits of being in a large market.

Given that the Chicago Cubs are one of the “favorites” (inexplicably) to win the World Series this year, at least according to those who are into MLB Betting Action, maybe Epstein’s “building” job is going more quickly than even he had hoped. Or maybe too many people like to throw dollars down on the Cubs.

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