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Ben Cherington has spent over a decade with the Red Sox in various capacities, beginning as an area scout, and later working in international scouting. Now the vice president of player personnel for Boston, Cherington has been a major force in the Red Sox’ success at acquiring and developing young talent. I spoke to Ben this week about a variety of subjects revolving around the Red Sox system and Boston’s approach to the draft and player development, and today we cover the draft and this year’s international market

Kevin Goldstein
: Over the past few years, the Red Sox have been one of those teams that seems to consistently select players in later rounds who have, for lack of a better term, “signability problems,” and quite often you sign those players. Can you talk a little bit about the philosophy behind that?

Ben Cherington: I think the way we look at the draft is to acquire as much talent as we can. We look at the talent each year and try to maximize the potential impact in every round. In the past two or three years, that’s meant taking players that perhaps fell a little bit in the draft for various reasons. In doing so, it’s part speculative, because we need time to get to know those players better and evaluate those players, both on the field and off the field, before we get to the point of deciding whether or not that player is worthy of an offer. It’s part of an overall draft philosophy that goes toward trying to view the draft as a vehicle to acquire as much impact talent as we can, year-in and year-out.

KG: With a lot of these “over-slot” type of picks, you don’t sign them until late, and at times there isn’t even an offer made until very late in the process-kind of collapsing the process to the very end. Why is that?

BC: I think the advantage of drafting in particular high school players, because they are the kinds of players that usually fit into this category, and waiting to make an offer-and in some cases we never get to the point of making an offer-but the advantage of doing that is that it does allow for a little more time to get to know the player. In essence, the scouting season is usually ending in the first part of June, and we’re getting until August 15th. We’ve used that strategy with several high school players over the last two or three years, and there’s a lot of them that we did a lot of work on during the summer, and we came to the conclusion that we were not comfortable offering a bonus anywhere near what their demand was. In other cases, after doing all of the work on a player, we decided that their asking price was closer to what matches up with our valuation of him, and we go ahead and try to get a deal done.

KG: How does one follow a high school player in the summer? What kind of environments are you talking about?

BC: It varies obviously, depending on what area of the country the guy plays in, but the player is usually with some kind of travel team or playing in a wood bat tournament, or generally some form of an All-Star team and the competition is a little bit better. So in some cases, we’re actually getting a better look than we did in the spring-especially with players from the northern part of the country with the bad weather and kids don’t pitch many innings or get many at-bats-it’s especially tough to evaluate those players.

KG: Again, this year you’ve taken a number of these kind of players, like Pete Hissey, Ryan Westmoreland, and Alex Meyer.

BC: Well, we’re really pleased with the progress so far. We’ve been able to sign most of our top 10 picks. In the three cases we haven’t, Peter Hissey and Ryan Westmoreland are two players that we were well aware of what they were asking for before the draft, and we drafted them with the intention of signing them, or at least making every effort to sign them. Although we haven’t yet. We’re working on it; you talk to the player and the family, and try to find some common ground. Any player we take in the first few rounds-certainly through the first five rounds-we’re not taking without some level of confidence that we will be able to get a deal done, and we’re going to work our hardest to see if there’s a deal to be had. With Ryan Lavarnway, our sixth-rounder, we’re optimistic that we’ll have something done there-it’s not done yet-but again, we’re optimistic on reaching an agreement and getting him in our system.

Past the 10th round, there are a number of high school players that we are using the summer to get to know a little bit better, and some of them have indicated to us that there really isn’t much of an interest in signing a professional contract, and so we’re expecting them to go to college, and we wish them well in doing so. Then there are a couple of guys who have a little more interest, so we’re taking more time to get to know them better and continue to gather information and talk to our scouts, and see if there’s a way-if it’s appropriate given our evaluation-for the Red Sox to sign a couple of these guys after the tenth round. We need to feel that there’s potential to add an impact talent to the organization.

That’s a hard decision, and that’s one of the benefits of taking these players and using the summer to evaluate these players and get to know them. And it is a different environment. There isn’t as much pressure surrounding it like before the draft, where these guys are worried about where they are going to be taken, and you can establish a little bit more of a personal relationship with them over the summer. That’s worked to our benefit in the past with players like Ryan Kalish and others. So we’re excited about this draft-obviously there’s a lot more work to do. We’ve acquired some good talent-guys who have a chance to be impact players-and hopefully we’ll hit on some of them.

KG: We’re talking about all of these over-slot players, but it should be noted that the Red Sox have found a lot of pretty great players at the slot as well. Guys like Jacoby Ellsbury, Justin Masterson, Jed Lowrie, and Michael Bowden were all pretty much slot-level signees. Is there just something that the Red Sox are doing differently?

BC: Well, [scouting director] Jason McLeod and our entire scouting department are working from the previous summer and through the draft, and compiling information on all of the players, and a lot of that is no different from other teams, but certainly we have confidence in the system that we have in place, and we feel that if we follow the system the way in which we normally do, more often than not it will lead to good outcomes. Still, we’re realistic about the draft, like every team is, and we know there are going to be misses. We know that we’re not going to hit on every single player we take, no matter what round it is or the level of investment. We do believe that even when factoring in these misses, at that time in the draft it was the right choice, and I’d have to believe most other organizations feel the same way.

In our mind, when we go back and evaluate our own drafts, we’re looking at what kind of impact we got out of each draft, relative to the investment that we made. We’re evaluating that in more of a macro-sense, as opposed to a micro-sense of evaluating each actual pick and which guy made it, and which guy didn’t. We do that also, but that’s more part of the off-season process of looking at our system and seeing what we have, and finding ways to be more competitive. In a macro-sense, we’re looking at our investments, and putting that in the context of what we’re spending in other areas of the operation. We feel that, based on the system that’s in place and our belief in it, as long as we continue to follow it, we have a good chance of continuing to get a good return. Therefore it is the right investment for the Red Sox to make.

KG: You’ve also been very active in the international market over the last few years, but this year, when the Latin American market really exploded, the Red Sox were relatively quiet. Was that a conscious choice, or were you in on a lot of these players and just ended up being outbid?

BC: Well, Craig Shipley oversees our international scouting department, and I don’t want to speak for him, but I think I can speak to your question in general terms. Craig and the whole international staff have a very high standard in terms of what they are looking for when it comes to making a significant investment in a player. And their track record speaks for itself. If you go back to 2006 or 2007 and some of the really big investments that we made-Engel Beltre, Oscar Tejeda, and last year Michael Almanzar-in all three cases, the player has progressed really well. Obviously we traded Beltre, but he’s shown a lot of good things in the Midwest League. Tejeda had some injuries earlier this year, so that hurt the start he had, but he has a lot of ability, and to be a shortstop every day in the South Atlantic League as a teenager speaks very highly of him. And then Almanzar, I believe he’s the youngest player right now in the South Atlantic League. So we’ve picked our spots in making these bigger investments, and you can’t argue with the track record. This year they felt-and just like we try to do in the draft-they felt that the asking prices for some of the players on the international market did not match up with their evaluations. That said, we did sign some players, and did spend some money.

KG: In talking to people with other organizations, there’s a lot of frustration with the draft and the international market. To be fair, none of the people I talk to blame the Red Sox per se for doing things the way they do them, but they do think it’s an indication of the player procurement system being broken.

BC: I guess it’s all relative to the team. We have resources, and we do things with those resources that maybe other teams can’t do-and it goes across all of our operations. We have the luxury of having a big payroll, and we also have the luxury to maybe give a scout a bigger raise when he gets an offer to go somewhere else. So it can impact a lot of different areas.

But it doesn’t guarantee success like we’ve all seen, and there are teams that have had a lot of success with fewer resources, and you have to give a lot of credit to them and we really respect them. Every spring training, we’re just a few miles away from the Twins, and they’ve served as a great example for us. Every time we sit around and we’re frustrated, or starting to feel sorry for ourselves because something isn’t going quite right, we look at a team like that-one that is doing a lot of excellent work with less resources-and that reminds us that there really are no excuses for failure with what we’ve got. We’ve got every chance to be good, and with our talent, at every level.

As far as things being “broken,” I’m not sure. I would think that if you went back over the last 20 years, and looked at farm system rankings, even the last ten years, using all of the different metrics that are used, there would be a lot of different organizations at the top. Some of those organizations would be “larger market” organizations, and some would be “smaller market” organizations. So there are a lot of teams with fewer resources who still had pretty good farm systems and developed a lot of really good players. As much as we continue to get better, scouting is still an inexact science. As much as we try to improve how we scout and how we evaluate players, and all the different things we look at, it’s still hard to project what an 18-year-old kid is going to do eight to ten years from now.

There’s no doubt we have an advantage, but as to the system being “broken,” that’s too strong to say it that way. The commissioner’s office is continuing to work to find a way to make the system work more efficiently, but within that context, our responsibility is to the Boston Red Sox. If we weren’t doing our job in the draft to the best of our abilities, we’d be doing a disservice to our ownership. If we didn’t go out and do what we’re doing in this area and do it wisely, we wouldn’t be able to continue to invest like this. We have to keep hitting on the right guys to keep doing things this way.

Coming soon will be the second part of this interview, in which we talk about having too many players at the same level and position, the resurgence of Daniel Bard, the challenges of having a team in the high-octane hitter-friendly environment of Lancaster, and why right-hander Michael Bowden was not a part of the Futures Game and will not be on the Olympic roster.

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