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Theo Epstein, Language, and the Shape of the Cubs’ Offseason

For a long time, I thought I’d be a lawyer. I liked the lifestyle—or, at least, my adolescent vision of it—and I reveled in the verbal back-and-forth I saw practiced by the profession’s televised representatives. But most of all, I liked the command of language the law seemed to require. To learn to say exactly what needed to be said, and no more? That was—and is—an exciting prospect for me. And it’s something I’m still working on today, even as my dreams for my career have turned ever-farther away from the world of torts and litigation.

Theo Epstein’s dreams, too, once included law school. Few remember it now, but Epstein pursued and completed a law degree at the University of San Diego School of Law while simultaneously serving as the Padres’ Director of Baseball Operations.

And his family has a long history with language: his father, Leslie Epstein, a novelist, is director of the creative writing program at Boston University. His sister, Anya, was a screenwriter for television for many years (her credits include Homicide: Life on the Street). Lastly, and perhaps most notably, his grandfather and great-uncle, Philip and Julius Epstein, jointly wrote a movie that I guarantee most of you have seen and, I hope, loved: Michael Curtiz’s Casablanca.

So when Theo Epstein speaks, I listen. And I don’t work too hard to parse what he’s saying. Because Theo Epstein, drawing on the totality of his experiences with language, usually says exactly what he means and no more.


Last Thursday morning, just a few hours before the on-field Cubs might have taken the field for Game Five of the National League Championship Series, their off-field leader, Epstein, instead took the microphone in front of a room full of reporters and set the tone for the offseason to come. My colleague Sahadev Sharma captured the spirit of that tone in his excellent piece yesterday. Today, I want to turn the focus more squarely to the specifics of Epstein’s comments, and what they mean for the Cubs moving forward. It all starts with this quote:

“As far as the obvious areas of improvement for us, the depth of our starting pitching we’ve already talked about,” he said. “Possibly improving our situational and contact hitting. Trying to improve our defense, especially our outfield defense, if possible. And controlling our running game a little bit more.”

Stop, and read that paragraph again. Do you think the Cubs are going to be targeting particular players this offseason? They won’t be. Instead, they’ll be targeting those four areas for improvement. If those areas for improvement lead them to particular players whose skills match the team’s need, of course they’ll go after those guys. But the arrow of causality will always run from the skills to the players, not the other way around. Epstein’s guys are too smart to do things any differently.

A caveat, before we go any further: I have no particularly special knowledge of what the Cubs’ front office is going to do this winter. I only know (a) what they’ve said publicly, and shared with the media on the record, and (b) that, for as long as they’ve been in Chicago, they’ve never tried too hard to “hide the ball” (as Epstein put it Thursday). What follows, therefore, is my take on what might be available to the Cubs this offseason, given their preferences and possible resource base. I could, of course, be totally wrong in everything I write here. You have been warned.

With that out of the way, let’s take a look at each of the four areas identified by Epstein in turn (each preceded by a quote from his comments on Thursday), and get a sense of what might be out there and available to the Cubs. Over the next few weeks, my fellow authors and I will dive in much greater detail into each area; consider this piece an overview that puts those more granular pieces into context.


Starting Pitching

“We want to continue to add impact pitching; we want to continue to add starting pitching depth at the big-league level, and I think … we need to continue to add young pitching to the minor leagues. I do think it’s a year that the pitching is going to burst onto the scene a little bit.”

Let’s get this out of the way right off the bat: I think any dreams you have of adding David Price this winter have to be abandoned. Whatever it is that you think about when you think about him, it probably isn’t “starting pitching depth,” and although he does fit the profile for “impact pitching,” his market will reach exceptional heights this winter—heights perhaps too high for the Cubs. I don’t know for sure. I do know this: it would be extremely out of character for this front office to lock up, for a half-decade or more, $50 million a year in the fragile arms of just two starting pitchers, both of whom would be playing the entirety of their contracts after age 30.

Instead of going after Price, I’d expect the Cubs to target older, cheaper, starting pitchers during free agency—think Brett Anderson, Ian Kennedy, or Scott Kazmir—and younger, cost-controlled arms with upside in trade talks. With respect to that latter group, I don’t have a clear sense of who the team might target, but I know that they’ve been interested in Carlos Carrasco in the past, and Sahadev Sharma has pointed to Julio Teheran, Tyson Ross, and about a half-dozen others who they’ll at the very least inquire on.

How will they acquire those young pitchers? Well, there’s this, again from Epstein: “We may be forced into a situation where the right move is to take away somewhat from that position player group in order to add impact pitching. I don’t know. I’d love to keep the position player group intact, and just add pitching without giving up any players. I’m not sure that’s going to be possible given the nature of our situation, and given what happens in the market, I don’t know.”

Remember: Epstein says exactly what he means. And what he means now is that it’s probably time to deal some of the Cubs’ young position players. I’m sure it’ll upset a lot of Cubs fans, especially given his performance in the playoffs, but look for one name to feature in a lot of those trade discussions: Jorge Soler. Yes, he’s quite possibly a future star, but the Cubs have a lot of those these days, and Addison Russell, Kris Bryant, and Kyle Schwarber aren’t going anywhere. Given their comments in recent weeks, and given the structure of their present roster, I’d expect Epstein and company to deal from a position of strength this winter in order to supplement an area of relative weakness.

Outfield Defense

“A lot of it depends on what we do in center field, [and] where some other players on the diamond end up getting the bulk of their playing time. The one thing you can take to the bank is we feel like the more options we have the beter.”  

There’s a number of guys who come to mind when it comes to outfield defense, Jason Heyward most prominent among them. He’ll command top dollar, just like Price, but that’s where the similarities between the two end. Granted, both have birthdays in August, but Price is turning 31 next year and Heyward 27. Price, moreover, carries with him all the risks that inevitably come along with an arm that can throw a baseball at 100 miles per hour. And Price, unlike Heyward, can’t improve the Cubs’ outfield defense in 2016. I don’t know enough about the Cubs’ finances to say for sure whether they have enough money to sign Jason Heyward. But I’m pretty darn sure that they’ll try—he checks off far too many boxes for this newly ascendant club.

What boxes are those? Well, first of all, he’s the same age as Anthony Rizzo and Starlin Castro, and his projected career arc therefore fits neatly into that of the team’s young core. Secondly, it’s easy to imagine him creating value in Chicago many years into the long-term contract he’s sure to sign this offseason. In the early years of the deal, he’d likely man center field for the Cubs. As the years pass, and prospects like Albert Almora, Jr. and Donnie Dewees force the issue at the major-league level, he’d be able to shift over to right field and provide excellent defense there too. Sure, those scenarios probably demand a Soler trade, but it’s clear now that that’s hardly off the table. Looking for a final reason? How about this: he’s a really, really good major-league player—in 2015, among the top 15 in the league by WARP.

Other possibilities? Denard Span is an option, as is Gerardo Parra. Parra’s defensive numbers were pretty rough last year in Milwaukee and Baltimore, but his numbers in Arizona were very solid, and he’ll come relatively cheap. In principle, I love the idea of Alex Gordon in left field, but that would require moving Schwarber behind the plate on a regular basis, and that just won’t happen in 2016. The perfect scenario for the outfield in 2016, at least for my money, is signing a cheap, high-contact fourth outfielder to a short-term deal, adding Heyward to the mix, and shading everyone a few steps toward Schwarber so that the latter has a little less ground to cover in left field. That said, a thousand different things could happen this offseason, and my dream scenario probably won’t.

Contact Ability

“It doesn’t make a lot of sense for us to go out right now and add a boom or bust high-strikeout, high-power, right-handed hitter into our mix right now. It would probably make more sense to go the other way and find a player who has a lot of his value wrapped up in being able to put the ball in play on a consistent basis, being able to get on base in front of the middle of our lineup.”

So what about that high-contact outfielder I’m dreaming of? Well, Span would fill that role well: he makes contact about 90 percent of the time, and has a good clubhouse reputation. Chris Denorfia and Austin Jackson, on the other hand, are probably gone (both sit in the mid-70s in terms of contact rate), although I wouldn’t put it past this front office to prioritize continuity and bring one or both back. Justin Maxwell is out; he’s in the high 60s. Colby Rasmus, who has a skillset I otherwise like, is probably not an option either (low 70s). That leaves Span and … this young center fielder out of Chicago, Dexter Fowler. Ah, yes. Fowler. What of his future with the organization? Let’s start with what Theo had to say on Thursday:

“Well, first off, Dexter Fowler had an unbelievable year. He fit in tremendously well in this organization, and I think really highly of him as a player and a person. He made a wonderful impression, [and] certainly there’s an interest in sitting down at the appropriate time with Dexter and his agent, Casey Close, and seeing if there’s a way to keep him as a Chicago Cub.”

I really like Dexter Fowler. He filled, as a center fielder with a leadoff profile at the plate, two huge areas of need for the 2015 club. But it’s time to let him walk. He’ll command at least three years on the open market, and that’s one year too many to commit to someone of his skillset when a high draft pick is on the line, as it will be when he gets his qualifying offer in the next few weeks. So I think the Cubs will and should let Fowler walk. That doesn’t mean they won’t sit down, as Theo said, and explore possibilities with him and his agent (two years and $34 million is something I think the Cubs should go for, for example), but I have a dim view of their parties for coming to an agreement. The two groups need different things out of a deal right now, and I’m fairly confident they’ll go in different directions in a few weeks’ time. Nothing in Theo’s statement makes me think otherwise; that’s just a smart man talking positively about a good player.

But the outfield isn’t the only place the Cubs could add contact ability this offseason. We know they’ve been interested in Ben Zobrist for many years, and he’s a free agent now, at age 35. He brings a lot to the table: the ability to play multiple positions, a high (88 percent) contact rate, and leadership ability that we already know meshes well with Joe Maddon’s. I’d expect the Cubs to make a run at him, and—if they get him—rotate him between second base, third base, and the outfield on a regular basis. Another name that fits here? Daniel Murphy. I know, I know. There’s the inflated price tag that’ll come with what he’s done this postseason, and he’ll likely get a qualifying offer from the Mets, which will further increase his acquisition cost. But he’s a high-contact left-hander who can play multiple positions of need for the 2016 club. Don’t be surprised if the Cubs make a run at him.

The Running Game

“A lot of [our goal this offseason] is just points of emphasis with coaching and heading into spring training and work, it’s just work. We can improve our defense with work, we can improve the control of the running game with work, we can work on situational hitting.”

Whew! That’s a lot of reading. But we’re now at the final area Epstein targeted for improvement: control of the running game. And here, I don’t think the team will do an awful lot in terms of player acquisition. Miguel Montero still has two more years on his deal, and David Ross—who’s already announced that he won’t retire this offseason—will join him on the roster next season, on the final year of his deal. With Kyle Schwarber locked in as the third catcher on the roster, that doesn’t leave a lot of room for a new catcher on the roster.

Except that catchers aren’t the only ones who are responsible for controlling the running game. In conversation on Thursday, Epstein noted that “[picking off runners is] not only the catchers’ responsibility, but the pitchers’ as well.” Cubs pitchers will have to learn to make their deliveries quick to home plate next year, and they’ll have extra help from their organization this year. Count on Cubs’ leadership making controlling the running game a priority this fall, and expect to see even more of it during Spring Training, 2016.

In fact, there’s only one change I see coming on the catching side in 2016, and it won’t play out this offseason. Willson Contreras, the young catcher for the Cubs, finally had the breakout season many hoped from him in 2015, slashing .333/.413/.478 over 521 Double-A plate appearances, and growing as a leader all the while. He’ll start next season at Triple-A, and could force his way onto the big-league roster with continued performance at that level in the early part of the season. If that happens, look for either (a) a Ross retirement or (b) a Miguel Montero trade. I’m not saying Contreras will definitely make the big club in 2016, by the way—only that it wouldn’t shock me if he does. (I should also note that these ideas are not entirely my own: a great deal of credit for them goes to Sahadev Sharma, who’s discussed the Cubs’ catching situation with me at length over the last few days.)


The Cubs have been a joy to watch since Theo Epstein and company took over three years ago, and for me to cover in 2015. They’ve dedicated themselves to a single goal: getting to the playoffs every year, and eventually winning the World Series. In so doing, they’ve transformed their organization. That transformation will of course continue this offseason, and that means changes on the North Side. In amongst that change, though, look for some key values to remain constant.

One of those constants—and perhaps the most important one—will be this: the Cubs will not target any particular player this offseason at the expense of acquiring skillsets that will fill areas of need they’ve identified for the 2016 club. Is Alex Gordon a good player? Yes. There’s no doubt about that. Is he a player who possesses the skills the Cubs need right now? No, he is not, for all the reasons we discussed above. And Epstein managed to say exactly that on Thursday, without even mentioning Gordon’s name.

I’m not going to be a lawyer. I know that now. But I still love language, and I love the way Theo Epstein uses it. Read his words carefully, and you’ll have a good sense of what might come to pass in what’s sure to be a fascinating offseason in Chicago. Again, over the next few days, look for pieces from my fellow authors, breaking down each of the four areas discussed here down in much greater detail. For now, onwards.

Lead photo courtesy Rob Grabowski—USA Today Sports.

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8 comments on “Theo Epstein, Language, and the Shape of the Cubs’ Offseason”


Rian, I kind of mapped out my own vision of offseason & we’re in total harmony. For me, the key is Heyward, as he checks so many boxes-to your point. He’s the quintessential Theo/Jed guy , in terms of supplemental skills that he brings.

As far as the pitching, I’d agree they need to be opportunistic in FA-where I assume they’ll get their mid-to-back rotation guy. The biggest question with the pitching is who and how many among Castro, Baez, and Soler is it going to cost to acquire the young cost-controlled guy? If it’s just Soler, I like the scenario where you have Heyward in CF, Bryant in RF, and Javy @ 3B….

Rian Watt

Man, I like that scenario too, and glad to hear we’re in harmony! I don’t know how much I like packaging two of Soler+Baez/Castro together, just because that’s a lot of talent to give up at once. That said, we’ve seen how well that can work out (Samarzija+Hammel = Russell + …). So we shall see! It’ll be an interesting offseason.


A great read — loved the you talked about particular needs and skills without getting too wonky. Heyward does seem like a good fit for many reasons, which leaves some questions about Soler. I love his power and potential, but his D and injury history makes me think the Cubs might want to sell high on him.

Rian Watt

Thanks, Joel. Tried to strike the right balance. And totally agree that the Cubs will and should look to shop Soler.


Couldn’t agree more!
I said it after Theo’s presser:
1) Heyward
2) Trade Soler/Schwarber (But Schwarber isn’t happening)
3) Sign a Lackey-type FA (old, still productive) to 1–2 year deal.

Regarding your “Contact Ability” paragraph, you forgot one name, and it’s just one more box to check for JASON HEYWARD.

#12 in K rate and #14 in Contact Rate among all outfielders.

Rian Watt

Very glad you enjoyed it! And yes, Heyward checks a lot of boxes, including (very much) contact ability.


Really enjoyed this. Would add Fister to the list of older/cheaper pitching signing options as well.

I do feel the Schwarber defense is a little overblown. Ben Lindbergh talked about this in a Grantland piece last week. He looked awful in the NLCS, but season numbers weren’t terrible. If he put up a -4 UZR like he was projected for this season, I think we would all take that.

What I am really interested in knowing is what do we think it takes to get a Carrasco or Ross?

Rian Watt

Totally agree on Schwarber. Hopefully putting together a piece on that shortly. He’s going to get attacked for his defense for a while because of his performance in the NLCS, but it just isn’t true that he’s that bad.

As for Carrasco or Ross, no idea yet!

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