Harvesting Opinion: Chicago Cubs – Theo Epstein Compensation

Harvesting Opinion is a regular feature on Seedlings to Stars. Every few weeks, a handful of FanSided’s MLB sites send S2S a question relating to their team’s minor league system, and we answer them in this space–each question gets one article devoted to answering it. In this way, we make sure we regularly get to discuss hot-button issues relating to the systems of every team, as we cover the teams in a regular, recurring cycle.

In this edition, we tackle a question sent to us from our Chicago Cubs site Cubbies Crib:

The Cubs and Red Sox are believed to be locked in tense negotiations regarding the compensation being sent to the Red Sox for allowing Theo Epstein to leave the Red Sox organization for the Cubs’ front office. The Red Sox are believed to be looking for the next “Kevin Youkilis” in return for Epstein. With that said, who in the Cubs’ farm system is the next “Kevin Youkilis”? Would said prospect be worth giving up for Epstein?

Nathaniel says:

Well, first, you have to figure out what is meant by “the next Kevin Youkilis.” Should we take it literally, as in, a high-OBP, medium-power 1B/3B with a solid glove? Or should we take it figuratively, as in the Moneyball sense of an “sleeping giant” in the system; a guy nobody talks about but who nevertheless could develop into an above-average big-leaguer.

If you take it literally, then you’re obviously dealing with a much smaller subset of players to pick from, and there’s no obvious match for a Youkilis skill-set. The Cubs have long focused on raw athletic types more than polished players, and as a result, most of the power-oriented corner guys they have are rather uninteresting, old-for-their-levels guys who a big-market team like the Red Sox would likely have little to no interest in. I suppose if Bryan LaHair counts as a prospect, that would be something of a fit, but I don’t see the Red Sox taking him as compensation.

So we have to turn to the more figurative definition, which basically turns this question into “Who is the most underrated prospect in the Cubs system?”

Just about all of Chicago’s underrated prospects are pitchers, which works nicely for the Red Sox, a team that was undone by a lack of pitching down the stretch in 2011. The seven pitchers I’d point to are RHPs Dae-Eun Rhee, Aaron Kurcz, Yao-Lin Wang, and Nick Struck, and LHPs Jeffry Antigua, Austin Kirk, and Chris Rusin.

I’m not going to get too in-depth about any of those seven, because I’d probably be pushing 2500 words if I did. All of them, though, posted very solid numbers in 2011, particularly in the K/BB department. Save for Rusin, they all were somewhat young for their levels, and Rusin pitched well in Triple-A and is basically big-league ready, so his age isn’t a big issue.

As for what they should be willing to give up, I come down on the side of generosity here. I know a lot of people are saying the Cubs can’t really afford to give up more than a nominal prospect, but I think they can afford to part with something more substantial, even top prospect Brett Jackson. In fact, I don’t know if there’s a single prospect in the system that I wouldn’t trade for Epstein straight-up. After all, there’s not a ton of serious impact talent in the Cubs’ farm, so what you’re basically doing by trading even somebody like Jackson is betting that Theo and Jed Hoyer can find one more average starter than an average front office in their tenure. That seems quite within their capabilities to me.

Of the above group of arms that I mentioned, I think the Cubs could send any two to the Red Sox and still feel quite good about the move. After all, they’d still have five solid pitching sleepers in the system, and the bust rate for pitchers is pretty high, so at most they probably would end up parting with a 3/4 starter and a middle reliever.

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Wally says:

It’s really not a part of the question but I’m not a fan of the concept of trading a player, any player, for front office personnel, manager, scout, etc. Even dealing a bag of balls and some bats strikes me as both excessive and unnecessary. After reading Nathaniel’s response above you’re already well aware that we disagree with respect to fair compensation amounts to in this case.

That said, let me be clear that I don’t fault the Cubs for working out a deal to acquire Epstein and I certainly don’t fault the Red Sox for letting Theo go with the understanding that they will be compensated. Both sides are working within the system to get what they want so kudos to them. On some level these deals – regardless of the sport involved – just rub me the wrong way.

To answer the question at hand, first we need to establish that there is only one Greek God of Walks. Guys that hit 0.298/.442/.441 in the minors and carry that over to a 0.289/.391/.492 line in the majors don’t grow on trees. I will say that I think Nathaniel is underrating Youk’s value and standing as a prospect, but  to be fair I don’t think anyone thought he would turn in 3 straight seasons with a SLG between 0.545 and 0.570. That part of his game was a bit of a surprise, but the BA and OBP that we’ve seen from him at the major league level isn’t really all that surprising based on his minor league career and his profile as a player.

Since my esteemed colleague tackled the pitching side of the equation, I think it makes sense for me to look at the position players. When we’re talking about a “Kevin Youkilis” type player, I’m looking for a guy that can turn in multiple 120 OPS+ seasons in the majors. Something that Youkilis has done the last 4 seasons now.

Assuming we’re looking for guys not yet in their prime years, we can probably rule out Brian LaHair (29). Even though he’s a lefty I think he would be a sight to behold hitting in Fenway and I know Nathaniel would be elated to see the guy have a legitimate and long term shot in the big league.

I’m wandering aren’t I? Sorry … sorry … back to the question.

The guy among Cubs prospects that appears to best fit the bill is OF Brett Jackson. Almost universally ranked among the Cubs top-3 prospects this offseason he’s a well known name and with good reason. He’s made better contact than expected as a professional and if that continues he has all the tools to be an above-average major leaguer. He’s hit 0.292/.393/.491 in his first 3 seasons and he exceeded those slash stats in 48 games at Triple-A this past season. Jackson has a very real chance to be a 20-20 guy in the majors and I think he will exceed that level of production. The problem for Boston is that Jackson is assuredly a part of the Cubs future and since they’re already on the job Theo and Jed aren’t going to deal him.

The next three guys on my list would be 3B Josh Vitters and OF Matt Szczur. They would be followed by another grouping that includes OF Reggie Golden, SS Junior Lake, SS/2B Marco Hernandez and Ryan Flaherty.

While a guy like Golden, or any of the other three in that grouping, would be a decent return, we know the Red Sox are looking for more. Szczur, with his athleticism, upside and vastly untapped raw talent, probably falls right behind Jackson in terms of position prospects the Cubs can’t afford to deal.

That leaves Vitters as  probably the best fit for the deal. He recovered from a disappointing half season in Double-A in 2010 and was fairly solid in 2011 while repeating the level. The question that Cubs need to answer internally is whether or not they believe Vitters can approach the lofty expectations many had for him when he was the 3rd player taken in the 2007 draft. Can he better than 0.280/.320/.440 hitter we’ve seen through 5 minor league seasons or is that simply who he is (understanding that those numbers will likely decrease against AAA and MLB pitching if he doesn’t improve)?

Chicago also needs to assess whether or not his improvement was real or simply a byproduct of repeating the level. If it’s the latter, the Cubs would be wise to deal him since he still has youth on his side and still retains some prospect “glimmer.” On the other side of the deal the Red Sox would be getting more than fair value and a change of scenery and organizational philosophy might be all Vitters needs for things to click.

Obviously based on the beginning of my response I don’t think Theo Epstein is worth giving up any player, let alone a guy – like Josh Vitters – who has a chance to be a valuable big league player. But at this point Theo is already working for the Cubs and some compensation needs to be worked out.

Vitters seems like a nice “compromise” to finish off the deal. The Cubs can point to the fact that Josh hasn’t lived up to expectations and the Red Sox can point to the fact that they acquired a player that was a MLB Top-100 prospect for three years (from 2008-2010), is still just 22 and appears ready for a stint in Triple-A next season.

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