Put on a scouting director hat and ask yourself this question: Do you want your team to do poorly so you can have the maximum number of opportunities to select a premium draft pick, or do you want your team to win – knowing all the supposed “top of the line” talent will already have been taken?
The question is purely rhetorical. For the person directing the draft and all the scouts out scouring for talent in the smallest of towns, the ring is the thing.
But that doesn’t mean you can’t win and have fun on the scouting side, too.
In 2004, the Boston Red Sox – down 3 games to 0 in the American League Championship Series against the New York Yankees – rallied to win their final eight postseason games in eliminating the Yankees and sweeping the St. Louis Cardinals. In the process, they won their first World Series since 1918.
On paper, if no free agents switched clubs, the Red Sox would have picked 28th overall in the ensuing 2005 amateur draft – with a second pick coming in at No. 58. But baseball isn’t played on paper. After the annual free agent signing frenzy, the world champs lost Orlando Cabrera, Derek Lowe and Pedro Martinez, and now – thanks to compensation selections and supplemental picks – found themselves with six draft choices from No. 23 to No. 57.
So … to the victors did go the spoils.
Oh, there’s just one thing. They were about to restock with a first-time scouting director.
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In November 2002, Theo Epstein – just 28 years of age at the time – was named general manager of the Red Sox. Earlier that year, he had joined the organization as the assistant GM after coming over from the San Diego Padres.
During his time in San Diego, Epstein struck up a friendship with Jason McLeod, a former minor league pitcher who began his Padres career as a Community Relations intern in 1994 – before moving over to Stadium Operations that winter and to the Baseball Operations Department in the fall of 1995 (Epstein had joined the team earlier that year). McLeod’s time with the Padres later included three years as a minor league coach, a return to the front office as the assistant director of scouting and player development, and two years as an area scout in Southern California.
Epstein brought McLeod to Boston as an associate scouting director in the fall of 2003, assisting David Chadd. After the Red Sox won the 2004 Fall Classic, Chadd moved on to Detroit to become the Tigers’ vice president of amateur scouting – and McLeod was promoted into the scouting leadership position. Epstein wasn’t concerned about inserting his former Padres cohort into that role despite McLeod’s relative lack of experience in the draft room.
“Jason and I grew up together in the Padres organization,” Epstein said in an email, “so I knew he could really evaluate and was a great leader.
“It was a seamless transition because Jason had worked with us in 2004. The entire organization was focused on the draft with all the picks we had, and Jason did a great job as always leading the department. We had a lot of fun all scouting season and in the draft meetings.”
McLeod acknowledges that he didn’t have a boatload of experience from a draft-day perspective when he took over.
“In ’04, I was instilling and re-doing the processes of it,” McLeod says. “David was absolutely the scouting director; he was pounding it out on the road. But from the front office side of things, we were kind of co-directing that department that year.
“During my time in San Diego, I had sat in on many draft meetings, but I hadn’t been in the director’s seat or calling the shots or instituting processes or things like that until I got to Boston.”
The Red Sox had broken the curse. Now, just a few months later at their January scouting meetings, McLeod was presiding over the group and putting a game plan into place.
“There was a lot of excitement, obviously, coming off the World Series year,” he says. “For those of us in amateur scouting, we were just as excited knowing that we had two first-round picks and three sandwich picks. We felt that we were going to get a couple impact players with the volume of picks that we had. And coming out of the prior summer – after scouting the Cape, scouting the Team USA juniors – we knew that it was going to be a really good draft.
“We told our guys, ‘Let’s get after it and go crush it and find as much impact and upside as we can.’”
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The top tier of the 2005 draft was considered to be very deep, and the results continue to speak for themselves.
The Red Sox knew they had no chance of landing any of those five – or high school outfielders/future all-stars Andrew McCutchen and Jay Bruce, who went 11-12. But there was still a lot of talent out there to be had. Boston had the No. 23 and No. 26 selections in the first round – along with the Nos. 42, 45 and 47 slots in the supplemental round. The team’s second-round pick was No. 57 overall.
The key was to be prepared for anything and everything. Back in 2005, the draft was conducted via a conference call – and there was very little time between picks.
“At that time, we did a lot of mock drafts,” explains McLeod, who is now the Cubs’ senior vice president of scouting/player development. “We would run a mock draft where different scenarios were happening. I think at that time we maybe had 30 seconds before the next pick. So we ran a lot of simulations in the room. Theo liked to try to set up scenarios where … there were 12 of us in the room, and he’d set up scenarios and go worst case. I’m sitting there watching the board, and he’d set it up and say, ‘Now this guy and that guy are gone. Where are you going here?’ And he put you on a timeclock. We probably did that about five or six different times where we ran those simulations.
“We felt good about the information that we had. We felt good about the performance metrics we were looking at, and about how we had the board stacked. So at that point, let’s run the simulations. ‘Now, he’s gone. Now these two guys are gone.’ We also ran some where we knew there would be no way the board would fall that way, but if it all blew up, ‘Now where are you going? Why are you doing that?’ So you do those things prior to draft day. You trust the process and you trust the preparation.
“At the same time, just like every draft year … as the pick is getting close, there is some anxiety and anticipation that you feel. But again, you just trust your process. You do all the work to be prepared for every situation.”
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By draft day, the Red Sox had narrowed their focus to three collegians for the No. 23 selection – Oregon State outfielder Jacoby Ellsbury, Arizona outfielder Trevor Crowe and Texas A&M shortstop Cliff Pennington.
“We spent so much time talking about those three players in particular, because we were really hopeful that one of them got to us,” McLeod said. “We spent an inordinate amount of time in the weeks leading up to the draft meetings on them. We kept stacking them and stacking them and talking about their strengths and weaknesses.
“The funny thing about Jacoby … that year, he had such a great year, and I saw four or five of his games – and he probably had his worst games when I was there. I actually took Theo to a game at the University of Washington when the Red Sox were in Seattle. Of course, Jacoby’s first two at-bats, he was 0-for-2 – and Theo was like, ‘Jason, you’re not allowed to watch his next at-bat. You’re bad luck. Please, turn around or something.’ So I literally turned around and heard the crack of the bat; I turned back and the ball was in the gap. Theo and I are standing down the third-base line, and I remember watching this kid round second turning on the afterburners as he’s coming into third. It was just something. You watch a lot of games and see a lot of fast guys, but then you see stuff that makes you say ‘Wow.’ That was one of those moments, just watching this guy fly around the bases. So I knew I wasn’t totally bad luck. I was in the ballpark. I didn’t see the contact, but at least I heard it.
“I literally saw him go 2-for-15 in a year that he hit over .400 and had an on-base of almost .500. But our scouts were so convicted on him – from the area guy (John Booher) to the regional guy (West Coast cross-checker Fred Peterson) to our national cross-checker (Dave Finley). They were all like, ‘This is our guy. This is it.’
“He was already doing the things that we were looking for … the ability to get on base … the fact that he was an outstanding athlete who was going to play in center field … he had a low K (strikeout) rate. My question was just going to be the strength. I remember seeing him in the Cape, and I was worried a little bit about how the ball was going to come off the bat.
“But there’s a really good story from that year. Oregon State was down at the University of San Diego, and it was one of the only days in the history of the University of San Diego that they actually had a rainout. San Diego’s coach, Rich Hill – who we had a really good relationship with – was gracious enough to let us work out Jacoby. So a couple of our scouts got to see him hit in the cage. Then they took him up to the Jenny Craig Pavilion, and there’s Jacoby Ellsbury throwing down gorilla dunks for our scouts – showing them his explosiveness and his athleticism. I wasn’t at that workout, but our cross-checker just called me and was blown away with the explosiveness in Jacoby’s body. He was like, ‘You will not believe what Jacoby just did.’
“If you looked at his performance, all the makeup we got on him, the fact that we felt that he was going to be ultra-disruptive on the bases … we thought he was going to be a shutdown center fielder. All of that aligned with someone that we absolutely wanted to bring into the organization. That’s why we liked Pennington. That’s why we liked Crowe. They were all these dynamic athletes that played in the middle of the field.”
Crowe went No. 14 to Cleveland. Pennington was chosen at No. 21 by Oakland. The Marlins, drafting after the Athletics and before the Red Sox, selected high school second baseman Aaron Thompson – and Ellsbury was Boston-bound.