Theo Epstein Speaks: Organizational Changes, Draft Pick Compensation, Use of Payroll, Rizzo, Jackson, More

theo epstein about thatChicago Cubs President of Baseball Operations Theo Epstein just wrapped an interview on The Red Sox Hot Stove on WEEI Radio in Boston, and I listened in, furiously jotting down every bit I could get. He touched on some very interesting stuff, but obviously stopped short of confirmed anything the Cubs will be doing this offseason.

What follows are my paraphrases of what Theo said, together with my own separately delineated thoughts, where appropriate. In other words, the “I,” “we” stuff is Theo. The parentheticals are me.

  • What’s different in the second offseason with a new club: Maybe a little more active. Second Winter is always different, because the first Winter you’re getting to know ins and outs of organization, and the players you have. Now there’s more of a comfort level. We’re also at a slightly different place – still building, but hopefully a year closer to being where we want to be. Can now be a bit more aggressive. (Me: This all squares with an approach that views 2014 as perhaps the opening of the Cubs’ next window, and maybe even shooting for a surprise in 2013. Makes me wonder what’s in store for what’s left of this offseason.)
  • What made you like Edwin Jackson: We like his age – plenty of prime years left. He’s also been the most consistent and most durable of the free agent pitchers. Because he’s bounced around, he’s underrated. You’d rather not be diving into free agent pitching, but he’s one of the relatively safest bets. We think he can be in the middle of the rotation for years to come.
  • The state of the Cubs’ organization, as it relates to signing someone like Jackson: The organization is a bit imbalanced, with more depth on the positional side. It’s next to impossible to build a rotation in one or two Winters, so we have to pick our spots (“get them when they’re available” – Theo actually used that line, which has been my mantra (not that I’m saying he got it from me (obviously), I’m just saying that apparently we’re on the same page in that regard)).
  • Thoughts on Ryan Dempster, who recently signed with Boston: Red Sox fans are going to love him. Extraordinarily healthy and consistent. Very competitive, and has evolved as a pitcher.
  • Thoughts on that huge Red Sox trade with Dodgers: Everyone in the industry was surprised by the scope of the deal, but I really liked the trade because of the young talent the Red Sox got back. We had scouted the Dodgers quite a bit because of the possibility of a Dempster trade with the Dodgers, and the caliber the Red Sox got in Allen Webster and Rubby De La Rosa is impressive. Everyone talked about the money, but not enough about the talent the Red Sox got.
  • On the Red Sox freeing up so much payroll, and what it means for an organization: The payroll that they freed up is also remarkable – but having available dollars at this moment in time, in this market, is not what it was 10 or 5 years ago. There used to be so much you could do with payroll flexibility – if you really wanted a guy, you could make sure you got him. You could do anything you wanted in trades. But nowadays, with TV money, a lot of teams have money to spend, and there are only so many ways to spend it. You’re really limited on the amateur and international side, so having a lot of money doesn’t necessarily help you as much as it would have in the past.
  • Thoughts on what a trade like that says about an organization, Boston in particular: If the trade was an indication that the organization is on the same page going forward on a united front, and are prepared to take a long view together, it’s a great sign for the franchise. The outlook of franchises evolve based on what they’ve been through. When you’re winning 95 every year, it can be hard to sell everyone on the idea that you have to focus on the long term. A terrible year like the Red Sox had last year can help bring everyone on the same page. (Me: Sounded a bit like Theo didn’t feel like he got that same support when wanting to focus on the long term.)
  • The difficult in finalizing deals when new information (like medicals) comes to light: If new information comes up while working out a deal, you have to incorporate that new information and try to re-work things – whether that’s a physical, or something else. (This was asked in the context of the Mike Napoli deal troubles, and the JD Drew previous signing issue, in which the Red Sox incorporated some health protections after originally agreeing to terms.)
  • Given that the Cubs have a protected first round pick, and would then instead lose a second round pick if they signed a free agent who’d received a qualifying offer, how do you view the value of a second round pick: Very important now – (1) don’t have the amount of compensation picks as in the past, so the second rounder is much higher; (2) there aren’t multiple paths into the amateur market anymore. You can’t give up high pick and then just try to pay some people big time later in the draft; and can’t go nuts internationally either. It’s a reminder of just how important it is to develop your own talent and not have to rely on free agency. There’s a real premium placed on draft picks right now, and it’s unfortunate the effect it’s had on free agents this year. Best thing that can happen for them is to be traded midseason so they aren’t subject to draft pick compensation (Me: Hey, I said that this morning!).
  • On whether the Cubs would thus avoid pursuing big-time free agents because of the lost pick and associated pool money: I can only answer generally, without speaking about any free agents left on the market. You can’t be dogmatic about it. There are free agents worth surrendering a first round pick, if the contract makes sense.
  • Thoughts on Anthony Rizzo’s development: He’s just about on the path we projected for him, but the remarkable part is how quickly he made a significant adjustment with his swing. He developed a dramatic uphill plane while in San Diego, in large part because of the park. Some folks though he wouldn’t make it because of that. We tried to buy low on him, then, and asked him to make the adjustment at AAA. It was clear as early as Spring Training that he had completely reworked his swing – very rare to do it that quickly and that successfully. He has a chance to be an elite player.
  • How you go about changing organizational culture: It’s fundamentally important, but very hard to define. You can set out to change the culture and make certain changes and bring in certain people, but it’s very hard to accomplish. It takes an organizational commitment, and you have to always stay on top of it. A big part of the culture I’d like to introduce is a winning culture, and I feel like we’re on our way despite the 101 losses. We got rid of a couple players who were causing some issues, and the clubhouse took a positive turn under Dale Sveum.

Brett Taylor is the editor and lead writer at Bleacher Nation, and can also be found as Bleacher Nation on Twitter and on Facebook.

71 responses to “Theo Epstein Speaks: Organizational Changes, Draft Pick Compensation, Use of Payroll, Rizzo, Jackson, More”

  1. Bill

    Could Theo be playing a game of smoke and mirrors with his comments about the value of the 2nd round pick? If Theo wants Bourn he wants him at a reasonable price. He certainly isn’t going to put up billboards saying we must have Bourn. So, how does he help drive down the markt price? By trying to convince teams that giving up a 1st round comp pick is too much for Bourn. I mean if Theo thinks a 2nd rounder is so valuable than giving up a first round pick must be reserved for guys like Prince Fielder caliber, not someone like Bourn. This would drive down the market interest and presumably the price and/or number of years Bourn will get.

    Maybe it’s just wishful thinking on my part, but I take with a grain of salt statements made byTheo regarding value of draft picks, etc. A GM isn’t doing his job if he’s not putting out false information so other teams don’t know what you are doing. It’s like in the weeks before the NFL draft and Team A is saying they love a certain player. You can guarantee that’s not the guy they want but they sure as hell hope the teams drafting ahead of them think they do so they draft this player so Team A can get the player they really want.