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Jason McLeod's first-ever draft pick as a scouting director was Dustin Pedroia, 65th overall in 2004. Since that point, in stints with the Red Sox, Padres and Cubs, McLeod has overseen the selections of talents such as Jacoby Ellsbury, Clay Buchholz, Anthony Rizzo, Joe Ross, Kris Bryant and Kyle Schwarber.

McLeod, now the senior vice president of player development and amateur scouting for Chicago, has seen the draft before and after the spending regulations put in place in the last collective bargaining agreement, he has seen it from big markets and a smaller one, and he has seen it from the perspective of a perennial contender and from that of a rebuilder. His team has picked as high as second overall; this year, it won't make a selection until no. 104.

With the draft around the corner, we chatted with McLeod on June 1 about all that he's learned in 12 years of selections—including the significance of makeup, the role of luck and the inescapable regret.

Tim Britton: How different is the draft now, especially since the last collective bargaining agreement, since you were first with the Red Sox?

Jason McLeod: Well, the biggest thing is certainly the draft pool and the bonus money that's allotted now. In Boston, we were able to be a lot more aggressive. There weren't really restrictions on what you could spend in the draft. You'd always talk to ownership, of course, and if things got out of hand with some of the signing bonuses, you might get a call from Major League Baseball. But you were allowed to be aggressive.

You look at a year like this year for us, not having a first- or second-round pick, and what that does to your bonus pool. I don't want to say limits you, because you're already limited by not having those first two picks. You're just not allowed to be more aggressive with limited money.

TB: How does that change the approach going in?

JM: It doesn't change the work that you have to do in terms of the evaluation of a player and the due diligence on the makeup and the background and so forth. In a year like this year for us, I think we have the lowest bonus pool out there. You really have to take into consideration, if you're going to consider overpaying for someone, what that does to your draft when you have such a minuscule amount of money. In other years when we've picked in the top 10 or top five, you're able to spread some of that around, and we've seen teams do that.

TB: Are there other consequences from those changes that maybe you didn't see coming at the time in 2011-2012? Has anything else changed that was more surprising to you?

JM: Signability has always been important, but now teams are working down to the finite penny of what they're going to be able to spend without incurring penalties. I think there's more of an anxiousness to make sure that the agreed-upon number once you draft a player is what that player is going to sign for. If a player doesn't sign, you lose that money, and it changes the rest of your draft and what you can or can't do. I think as we've gone through that for the first couple of years, teams have really really paid razor-sharp attention to the signing bonuses.

TB: As a scouting director, how do you evaluate your own evaluators?

JM: I think most of us in this position certainly build in mechanisms to try to evaluate how you feel about a particular draft. There's so much that goes into it. It's looking at prior evaluations, looking at your area scouts' pref list to making sure that you have the documents of how you actually lined the board up in your respective draft rooms. An area scout may have had his players lined up in the order they should have been, one through 30 or whatever on his list, but that's not necessarily the order they're going to end up on the draft board just from players from his area because there's a lot of discussions that go into it. There's signability, there's medical information. For teams that are heavily performance-based, they're going to weigh that a lot.

A lot goes into evaluating your prior drafts and how you did. We certainly learn a lot from it. I constantly do that. I look a lot back at our prior draft boards, and I write notes about how those conversations took place and how guys ended up at certain positions on the board. And you certainly try to learn from all the decisions you've made in the past so you can make better decisions going forward.

TB: How far back do you go in evaluating prior drafts? Is it 4-5 years or farther back?

JM: I try to go farther back, and I change the evaluation. I go back and look at every single year. Let's take for instance 2011 in San Diego. Right now, that looks like a pretty good draft we had. We had 10 guys make it to the big leagues and four guys currently in major-league rotations. So right now it looks like a great draft. A year from now, it might look differently. I always look at them every year. I'll probably go back about six or seven years.

TB: In Boston, San Diego and Chicago, you've had teams at each stage of the competitive ladder. How does that alter your approach going into a draft? Does it alter it at all?

JM: I wouldn't say it alters it too much. In Boston, we were more taking players simply to get them to Boston as soon as we could. It worked out that way with a couple of guys like Pedroia and Ellsbury and Buchholz that got there really quickly.

I think our mindset has always been to get as much young talent as we can. We do take into consideration the makeup of a player and bringing him into an environment like Boston or an environment like Chicago. Kris Bryant, case in point. Granted he was the no. 2 player overall, but just from a makeup standpoint, after the area scout did such a great job knowing Kris and having history with his college coach, Jed [Hoyer] and I getting to sit down with him — we all left that meeting saying if there was a guy who could handle the expectations in Chicago being the no. 2 overall pick, this is the guy. This is the way he's wired. And he's been that guy.

When we were in San Diego, certainly we were in a different cycle in terms of where the major-league club was. So Jed and I were trying to get as many good young players as we could to build up the farm system. We felt good about that. Certainly we were in that same scenario when we got here to Chicago. Theo [Epstein] was pretty transparent with what we were going to do in acquiring as many young players as we could and long-term assets.

TB: How different is it now in Chicago with you in a different spot competitively?

JM: Obviously it's a lot of fun with what's happening with the major-league team. The fans have not only rallied around the winning that's taking place but have really fallen in love with our young players — the Anthony Rizzos and Kris Bryants and Addison Russell and Jorge Soler. We've picked in the top 10 every year that we've been here, and now this year we're going in a situation where you go from picking top 10 four years straight to picking 104. It's going to be certainly different. It's a bit different the way we scheduled our coverage this spring. What doesn't change is our preparation and our expectation to do well in the draft.

TB: With a guy like Russell, when you're considering trading for him from Oakland, how much do you go back to your initial pre-draft evaluations of him? Or is it totally different once he's gotten into the minor leagues?

JM: I think you can go back to your amateur evals for makeup information, for sure. When you're trading for a guy who's still pretty young in his minor-league career who you don't know personally that well, you can really lean on the area scout that had him and the background information reports that he had on the person himself. And then with Addison, our pro reports were just so good on him immediately. We had seen him play the prior fall in the Fall League, and we were just blown away with how quickly he had come that far.

TB: In Chicago, you guys have placed an emphasis on bats coming out of the draft. What was the conversation like in prioritizing the offensive side over arms in the draft?

JM: Looking at where we were selecting, first we were picking six and we had two guys we were on really—Carlos Correa and Albert Almora. We were just shooting for upside there. Coming back with Kris Bryant, that was an easy one in '13. Schwarber for us, we spent a lot of time with Brady Aiken that spring and obviously he went one. Kyle we thought was the best college hitter in that draft. And then last year we came back with Ian Happ. We did like some of the college pitching. Obviously Carson Fulmer we were fans of. Tyler Jay we were a fan of. Those guys went before us. It hasn't been an aversion so much to picking a pitcher. It's just the guys that we would consider were gone last year, and the other years we had a lot of position players higher on our board.

TB: How deep in the draft can you reasonably project the picks these days? It used to be you could know where teams were going pretty deep into the first round. Is it still that way or is there more flexibility that night?

JM: It's kind of funny. When I was in Boston, we were picking a lot in the back end of the first round. We were running a lot of our own internal mock drafts with our group that was there, and I still have all those. We did a pretty good job with where we thought players might go or who might be available to us when we got to those picks. Coming over here and even in San Diego, we picked in the top 10. When you're picking that high, you have a really good idea of what's going to be available to you.

I would say in general that you probably start losing that ability to place guys around the end of the first round and sandwich round. For me, my history is the sandwich round is when teams start taking more chances on upside, some teams go for more of the sure thing on the college performance guys. For me, that's when it starts to get a little harder to predict what's going to happen in that area of the draft.

TB: When you're picking top 10, how big is the player pool for that pick? Do you rank the 10 guys you feel good about, and how different is that from the pool when you're picking in the 20s in Boston?

JM: Well, the first three years we picked six, two and four. We narrowed it down to the guys that we really really liked. With Kris, that was an easy one. It was him or [Mark] Appel or [Jon] Gray; we only had to talk about those three guys. Even if you're picking ninth or 10th, you pretty much have a really good idea of four or five definite guys that won't be there, if not more. You can probably zero in on two or three players.

My first year in Boston in '04, we were picking 65 and we lined 40 names up on the left and said, 'We feel confident these guys are going to be gone. If anyone's there, would we take him over our list over here once we get it going?' That's how we work that list. Dustin Pedroia was in that top 40. He was just such a strong performance guy, we figured someone would take him because the performance was ridiculous. He was still over there. In fact, we had him and Kurt Suzuki on that top 40, and we had Dustin right above him. We didn't think he would be there, and he was still there, so that was the guy we took.

TB: At what point that night do you start thinking this guy who you didn't expect to be available to you might be? What's the environment in the room when you notice that?

JM: It was just more surprise. Obviously, he's a smaller guy, he wasn’t a plus runner, wasn’t a plus thrower. But gosh, he had been a Team USA guy, three good years of performance. We got into the late 40s and thought, 'Wow, no one's taken Pedroia yet.' We get to pick 60 and he's still there. 'We might get Pedroia.' And then we start the, 'We're comfortable with Pedroia, right?' For us, Dustin just fell into our laps.

TB: What's the size of that board going to look like with pick 104 as your first one this year?

JM: That is something we're still trying to determine. It's hard because there's some volatility once you get into the sandwich area with teams going off in different directions. It's tough to say, 'These 70 guys won't be here.' We'll probably move all the guys we think will be gone by the competitive-balance picks. We still might move 40 slam-dunk guys for us off. Picking through some of the other guys, I would imagine we'll try to have about a list of 50 or 60 names. You don't want to limit it too much; you don't want to be surprised. There are so many things that can happen when you're picking where we are.

The thing for us, we're going to have that whole first day. It'll be different. We'll be sitting there pulling names off the board, but it's also going to allow us to clear all those names, regroup, and get ready for Day Two.

TB: Scouting directors almost always tell you they're looking for the best player available. Has there ever been a time in your career where you weren't going for best player available in a certain spot?

JM: There have definitely been a couple of times where in my mind I was going for more upside over what would have been the more prudent choice, if you will. I used to tell our guys I look at our draft as a portfolio every year. How do you want to choose to run your portfolio for that year? Is it going to be conservative? Is it going to be really aggressive? Are you going to diversify it in a certain way? I used to try to look at our drafts like that, so there were a couple years where if I thought we had had a couple of value picks — value stocks, if you will — and I wanted to go a little more aggressive. We did that with some guys over guys who were safer or you knew what you were going to get. We took a couple guys like that, so let's really get aggressive and go with this guy who has big upside but the risk is bigger. That's come back to burn me a couple of times.

TB: How frantic are the final 10 days before the draft?

JM: Everyone just got through the blitz that is the conference tournaments. That's always an exhausting week, especially for scouting directors and national guys that are bouncing all around trying to hit different tournaments and there are four games a day to get your last looks. The majority of the heavy scouting part of it is probably done for most teams. I'm sure you'll have guys covering the regional tournaments this week.

For the most part, evaluations are probably done. The area scouts are still trying to scramble to get some last-minute background information or some signability information for their respective clubs. That's what this last week and a half is going to be spent doing. 'Are we sure on the makeup? Are we sure on his health?' Really trying to tighten up all of that so when you have your board lined up, you don't have to worry about that.

TB: I remember Theo in Boston at that opening press conference talking about "a scouting and player development machine." How intimately tied is scouting with player development?

JM: That's why I love what I do so much, because I get to have my feet in both departments. It's the left hand and the right hand and it all ties into the body and all of the organization and upward to what the major-league team is going to be.

Certainly, even though the two departments aren't interacting together on a day-to-day basis, you have to have amateur scouting or your international staff understand what it is we try to do on the player development side — how we're going to develop the players fundamentally and mentally and all those things. The scouting staff isn't going to draft solely based on how player development wants to develop guys. They're always going to look for upside and talent and impact. But it's definitely a tool of information for them to have. When we talk to our player development guys, talk to our pitching coordinator or our hitting coordinator about the things they like to see, what's fixable? What's not? What plays at the upper levels? What's Joe Maddon looking for? What type of player is he looking for? It helps them to have that information in hand.

On the player development side, when you get these, in John Schuerholz terminology, when you get this bald marble, you have to understand what the scout saw in the player, why he recommended him to the organization and why we drafted the player.

TB: How much do you enjoy having that twin title in Chicago?

JM: I love it because the draft, I'm just so passionate about it. It's the one day a year that you choose who comes into your organization. There's so much work involved in it; all our scouts have put in all that time over the prior 12 months — all the miles driven, the evaluations that have been written. And then ultimately, it's just the competition of trying to find the best players, beat other teams on players with evaluation and information. So I love that part of it. I love the draft.

Then on the PD side of things, being involved in putting together a player plan for a player and seeing him get better and develop in all those areas, see him mature as a person and mature as a player, nothing makes an organization feel better than when you have that happen. To put that plan in place for him and watch him, whether he's 21 or 18 when he comes in, to watch him grow for those three or four years, it's just tremendous pride for everyone involved when that guy makes it to the major leagues, especially if that guy makes a significant impact on your major-league team. There are so many people that have touched that player along the way, it's just a great moment of pride for everyone.

TB: What's it like now to see the fruit of that system at the major-league level off to the kind of start it is this year?

JM: It's a lot of fun. The Kris Bryants of the world, you don't have to do too much with those guys. They're special players. You're happy for all of them, don't get me wrong. But those guys that had to grind their way level by level by level, a guy that had to repeat a level or go to multiple instructional leagues — when you see those guys break through, you know the hard work the player has put into it. You know all the hours your coordinators had been going through things you can do to help this guy. The time spent by a scout to see him a third time when it's a four-hour drive and he could have ticked off an easier guy closer to home and he made the trip anyway. All those things that a lot of times the players don't know about go into it, the people that are somewhat in the shadows, they deserve so much credit, and that's why we feel so wonderful when that happens.

TB: You mentioned looking at your own prior drafts. How much do you analyze what other teams do in the draft and see what their approach is?

JM: I definitely look at that a lot. You certainly want to learn from successful organizations and what they're trying to do. Obviously without having the inside knowledge of what's going on, I certainly look at teams that have drafted well, teams that have drafted certain positions well. It's always a learning experience. We might have had a player evaluated right and put him in the wrong place on our board. Why did he end up there? What was the conversation in the room that steered him to that spot where we didn't get him and now this team took him behind us? That's a constant, ongoing project.

TB: Clearly drafting is difficult, and you mentioned things coming back to burn you. It seems that no matter how good a draft is, there's always that one pick you could have made. How difficult is it to deal with that regret looking back? Do you get over it quickly or are there things that stick with you?

JM: I think a little of both. It depends on the process that you have which led to the other pick and how good you felt about that pick at the time. Certainly, gosh, every scouting director's closet is littered with, 'Man, I should have taken that guy. I should have listened to my cross-checker. We had this guy teed up and I went with my gut instead.' I know a lot of us have that. There might be one or two that bug me to this day, and it's probably more process-related and the reason why I made the other decision than the one that could have been made.

Tim Britton is a Red Sox beat writer for the Providence Journal.