”You can’t really go out and just like snap your fingers: ‘OK, now we’re ready. Now we’re going to spend money. You have to look at it as a gradual process with each offseason. Looking at the free-agent markets going forward for starting pitching, it was really attractive. There [aren’t] many [proven] guys that come out [at] 29 years old.”

Theo Epstein Speaks: Organizational Changes, Draft Pick Compensation, Use of Payroll, Rizzo, Jackson, More
By Brett on January 3, 2013

Chicago 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.

"We got rid of a couple players who were causing some issues"

So "The Plan" is basically just do whatever they think is good at the time?

Thoughts on Ryan Dempster, who recently signed with Boston: Red Sox fans are going to love him. Extraordinarily healthy and consistent.

The future holds the possibility to be great or terrible, and since it has not yet occurred it remains simultaneously both.

I might consider reading that shit if people understood the importance of text formatting. But a block of bullshit? I can make that myself in the morning.

So "The Plan" is basically just do whatever they think is good at the time?

I disagree with your joke, but even if true, it supports my premise. People can stop trying to act like they know exactly what the plan is.

I've laughed at how everyone assumes they know specifically what "the plan" is, and how the SPs they went after didn't fit (with the thinking that Theo and Jed must not understand their own plan or something). Here's a good explanation from Jed on why they do, and why they may still be attempting to sign a CF to a similar deal (likely Bourn):

http://www.bleachernation.com/2013/01/0 ... urn-garza/

If the plan wasn't to lay low on FA until they could clear bad contracts while selling hope with prospects than you should be up in arms about them stealing one and likely more than one season from you. However, if that is the plan, than Jackson is a shit signing.

I disagree with your joke, but even if true, it supports my premise. People can stop trying to act like they know exactly what the plan is.

My thoughts on it are, that in today's game you simply can't put together a team with the idea that "this is our outfield for the next ten years". It just doesn't work that way now. Although, with the new TV deals and the high price of pitching, we may see a move back toward largely homegrown teams just out of necessity.

The future holds the possibility to be great or terrible, and since it has not yet occurred it remains simultaneously both.

I have MANY years of experience in trying to appreciate steaming piles of dogshit.

I don't think it's an issue of knowing what the plan is. It's that the plan is so loosely defined that even the Cubs management can't define it well. If "sign players that can help" is the plan, then every team in every sport has the same plan.

My thoughts on it are, that in today's game you simply can't put together a team with the idea that "this is our outfield for the next ten years". It just doesn't work that way now. Although, with the new TV deals and the high price of pitching, we may see a move back toward largely homegrown teams just out of necessity. And Theo may be on the cutting edge of that idea, though I would guess it's incidental rather than some grand plan.

One thing that cannot be argued is that if a Kenny Williams team lost 101 games and he said he was proud of the winning culture he was building, he would be laughed at like a clown. And he would deserve it.

Do you think this golden age of TV deals is going to last much longer? It seems incongruously old-media. I feel like the entire cable industry is going to fall off a cliff when people start deciding not to pay out the ass for basic cable because ESPN and one to three RSNs are passing the rights fees to the cable providers and jacking up the prices for everyone whether they like sports or not. That's why I'm extremely skeptical of the Cubs starting their own channel. I don't think CSN is even basic cable anymore, is it? You're going to make people pay out the ass for Cubs games in a market that got to be what it is in part because the games were free over the air?

I am not a legal expert, how many times do I have to say it?

It's a bigger problem for the the B1G network when a la carte cable becomes a reality and nobody will pay for it.

It's a bigger problem for the the B1G network when a la carte cable becomes a reality and nobody will pay for it.

Do you think this golden age of TV deals is going to last much longer?

No. People act like they know the ins and outs of the plan. There is no way the Cubs have, or will explicitly state the plan in public. That doesn't make sense. They can talk about it in general, so people have a vague idea, and understand there IS a plan, but to lay out the Xs and Os would be nuts.

All a la carte does is change how you are billed. Most people won't save money, and anyone who lives with a woman or kids will pay more.

Meant people paying for the B1G. Not that the B1G shouldn't get all they can and expend while people want in.