Keith Law writes for ESPN providing analysis on all baseball topics.  He also writes about food, literature, and other subjects on his personal blog, The Dish.  You can follow Keith on twitter, @keithlaw. I think he’s a must follow for any baseball fan.  I’d also like to thank Keith for taking the time to do the interview with such a busy schedule.

Q: Since the regime change last winter, many baseball experts have said the Cubs have really smart guys running things and fans just need to be patient.  On the other hand, looking at Boston this year, you can make a legitimate case Epstein’s moves put the Red Sox in the predicament they were in before the Dodgers bailed them out.  What is your overall impression of the Cubs new front office? What do they do right? And why should Cubs fans be patient instead of skeptical?

I think they’re absolutely headed in the right direction, including spending money on Soler ahead of the implementation of the new CBA, going after higher-probability players in the draft without significantly sacrificing ceiling, and giving opportunities to potentially undervalued players like Bryan LaHair (even if that didn’t work out).

I don’t see why Cubs fans would be skeptical, though. What has the regime done so far to merit that skepticism? I also think that if you’re going to debit Epstein for the free agent disasters in Boston, you also need to credit Hoyer and McLeod for building the majors’ best farm system in San Diego.

Q: The new CBA was a total game changer especially for the Cubs who were just starting to exploit the old system’s market inefficiencies.  Except spending more than other teams on their 25-man roster, how can the team still use their financial advantage?

I’d expect them to be more active with players coming from NPB or KBO [Japan and Korea], since those players aren’t subject to the CBA’s limits on international players. I also think their financial advantage allows them to make moves where they take on a bad contract to get a player or prospect they really want – in effect, buying talent through an indirect route.

Q: Speaking of market inefficiencies, I recently published a study on the success rates of first round draft picks from 1990-2006. Overall, teams averaged ~30% success rate on their first round picks. However, the teams employing Tim Wilken were at 57%.  I’m a little disappointed the Cubs moved Wilken out of the Scouting Director position as he’s been so successful for such a long period of time. How do you feel about Wilken’s first round picks since joining the Cubs? Do you know anything about his new role with the team? What can you tell us about his replacement Jaron Madison?

I’ve known Tim for ages and have a ton of respect for him as an evaluator and a director – but I think your method is a little simplistic, primarily since first-round picks are almost never a unilateral decision by a scouting director. Almora was a group decision that included everyone we’ve discussed so far here, as well as other evaluators with the Cubs. My understanding is that Tim will still see potential selections for the team’s top picks, but it sounds like he’ll also be used more on the pro side, seeing possible trade targets and evaluating the Cubs’ own prospects, which is a great use of his abilities.

Q: What are your thoughts on Starlin Castro’s development and his recent extension?

Love the extension – the downside is extremely limited, so even if he doesn’t become the kind of star I expect him to become, it’s still a reasonable deal for the team. I’d like to see more improvement in his approach at the plate – more walks would be great, but I’d settle for better at bats – but I also think it’s going to take time for the new regime to implement that philosophy in the Cubs’ system. Plate discipline wasn’t a priority under Jim Hendry, and it’s a hard enough thing to teach even when it is a priority, so I’d expect it to take a few years before we’ll see an effect up and down the system.

Q: When teams call up their top prospects, they normally want to give them a lot of playing time. Josh Vitters on the other hand is being platooned with Luis Valbuena.  Why is that the case in this situation?  What’s Vitters future moving forward?

I don’t see a future there. He’s long had one of my favorite swings in the minors, but his approach is all but nonexistent, and I don’t see how he’ll ever hit enough to make that swing (and the power it could provide) matter in the majors. If he had Matt Dominguez’ glove, it’d be a different story, but Vitters is at the opposite end of the spectrum. 

Q: Can you tell us about the Cubs prospects you do like & when can we expect to see these guys at Wrigley?  

I’m going to defer that till I do my prospect coverage this offseason. There will be plenty of Cubs content in there. I’ll also see Javier Baez a bit in the AFL, so I’ll be writing about him more in October. I’m a big fan.

Q: On the 20-80 scale, how do you rate Matt Szczur’s present and future tools? You’ve been pretty critical of Szczur and his “short, slappy swing” saying unless that changes he will not produce any power at the majors.  What kind of chance does he have at being an everyday lead-off hitter type that brings value by getting on base, using his speed on the bases and playing defense despite a lack of power?

I don’t see him as an everyday player. He doesn’t have the kind of patience to be the player you describe, nor is he a 70 or 80 runner. I think he’s been overrated because of the bone marrow transplant story (which is an amazing thing, just not relevant to his future as a player) and because Cubs fans didn’t have better prospects to whom they could pin their hopes. Now you have Baez, Almora, Soler, Paniagua … players worth getting excited over. The Vitters and the Szczurs will get less attention as a result.

Q:  Some fans bring up Prince Fielder when talking about Dan Vogelbach’s chance to play first base.  I’ve always thought of Fielder as pretty agile for a such big guy which makes him a unique case.  Other than being fat guys who hit for a ton of power, are there any other similarities between the two? Is there any chance Vogelbach plays first base at the major league level?

Fielder’s a much better athlete than Vogelbach, even light on his feet considering his size, and Fielder’s not even a good first baseman. I can’t see Vogelbach playing any position but DH in the majors. He’s a one tool guy.

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