MLB Trade Rumors

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In the days and weeks leading up to the draft, there had been a lot of discussion in the Red Sox draft room – oftentimes heated – about hard-throwing Angelina College right-hander Clay Buchholz.

“Clay was someone I had to have,” McLeod says. “I was just in love with the ability and the athleticism.”

As has been documented, Buchholz was pitching for a community college team in Lufkin, Texas, for a reason.

“It’s out there … when he was at McNeese State, he and his friend did a stupid thing. They broke into a school and stole some computers from a computer lab,” McLeod recalls. “Obviously, we had to dig deep into (A) what happened here and (B) is this something that’s going to be problematic going forward.

“Clay was very upfront when we talked to him about it. Jimmy Robinson, the area scout, did a tremendous job on the background and getting to the bottom of that story – and getting to know the player himself. I met with Clay in Texas. Theo and I had a big discussion with him in Boston at our pre-draft workout. We had a long conversation with him out in the bullpen during batting practice one day and talked about it. ‘What’s important to you? How do you want to be remembered by your family when you’re done playing this game?’ We hit him with some pretty personal questions.

“Let’s put it this way … I made it very evident that he was someone I had to have in that draft. There were some arguments in there. There was a time when Theo definitely challenged my conviction on the player, and we had a pretty heated debate about it in the room. Theo, in so many words, said ‘Jase, this is your first year running a draft as a scouting director solo. Are you going to put your name on this guy?’ I stood up and said, ‘Yes, I am.’

“At the end of the day, we were obviously aware of his past. It wasn’t ideal, but I personally felt confident enough to push for him in the first round. I can tell you we didn’t make his selection with any ‘Hold your breath, let’s hope this kid doesn’t get into trouble’ thoughts. We genuinely felt like he made a mistake and atoned for it.”

Ultimately, putting a first-round tag on Buchholz was a little too rich for Boston’s collective taste to select him at No. 26. That – and the fact that a reliever the team thought should have gone off the board much earlier was sliding.

St. John’s University closer Craig Hansen had dominated Big East Conference competition that spring, striking out 85 batters in 64 1/3 innings and recording 14 saves. McLeod thought a team that wanted a quick-to-the-majors reliever that could potentially pitch in the back end of games relatively soon would have jumped on him.

“We didn’t think Hansen was going to be there, because coming off the Cape that prior summer and going into the year, he was just so dominant,” McLeod said. “He wasn’t a priority type coverage guy for us, because we thought somebody else would grab him before pick 23.”

While Hansen was available, he was not an option for the Red Sox at No. 23; that pick was earmarked for a college hitter. The last-second conversation at No. 26 reverted to Buchholz.

“The bigger discussion for me on the Hansen selection was … we had done a lot of work on Buchholz, and I thought the Dodgers were going to take him at 40,” McLeod says. “I knew Logan White liked him. I knew he was there to see his last start. My fear was that we were going to miss him. I just had to leave that draft with Buchholz. He was the gut-feel guy who I really wanted.

“So there were some discussions about him at 26. That would have been a stretch for the rest of the room and for a lot of our guys, but that’s just how much conviction I had in Clay’s ability. And then the conversation obviously went back to Hansen – a big, college, ‘get there quick’ guy. We knew what he was and we knew he had power stuff. So the decision was made to take Craig. We took him – and he got to the big leagues later that year.”

Although he did pitch in four games for Boston that summer, Hansen struggled as a major leaguer, seeing action in 95 games for the Red Sox and Pirates. He saw his last minor league action in 2012. “Unfortunately for us and for Craig, he didn’t have the career that we all thought he would,” says McLeod. (Boston did still get some value from that selection, as Hansen was part of a three-team blockbuster that netted outfielder Jason Bay, who had one and a half outstanding seasons with the Sox.)

With Hansen on board, all McLeod could do was wait impatiently for Los Angeles to make its supplemental round selection.

“I sat there and held my breath,” he remembers fondly. “I know now, having talked to other teams over the years, it was basically us and the Dodgers that were in on Clay. Logan White is a good friend – and obviously his track record is pretty stellar with the draft, and we’ve had fun talking about Clay over the years. But we sent one cross-checker to this tournament in south Texas, and I think it was the opening day of the college conference tournaments – and Logan happened to be there. It says a lot when the scouting director, instead of being at the SEC tourney or day one of the Big 12, is seeing a junior college guy down in Nowhere, Texas.

“When the Dodgers were about to announce their pick, I literally was like, ‘They’re going to take Buchholz. They’re going to take Buchholz’ (laughing). And then they took Luke Hochevar.”

After Atlanta drafted high school left-hander Beau Jones at No. 41, McLeod got his guy.

“There was a big exhale … relief. Anyone who worked with me at the time would echo the sentiment,” he says. “As a scouting director, he was the guy I had to have in that draft.”

Fast forward to two years later, and Buchholz threw a no-hitter in his second major league start.

Rewind to draft day, and McLeod had about 60 seconds until his next pick at No. 45.

“We had stacked the board with some college hitters that we liked, so I was already feeling confident about our next pick,” recalls McLeod. “There were a few guys we really liked: Jed Lowrie (Stanford) … Stephen Head, a kid from Ole Miss … Chase Headley (Tennessee). I knew we were getting one of those guys.”

Sure enough, the Cardinals and Marlins picked pitchers.

“Jed Lowrie fell right into our laps – a guy who played the middle of the field with that kind of performance in college. Nowadays, he’d never get to No. 45. For us, it was a no-brainer. This kid was coming off a sophomore year where he almost won the Triple Crown in the Pac 10. He had a little bit of a down junior year, which allowed him to slide down into that selection for us.”

Then, two picks later, the Red Sox went the prep route, selecting Michael Bowden – a pitcher out of Waubonsie Valley High School in Aurora, Ill.

“Michael Bowden was a kid that we spent a lot of time with,” McLeod says. “He was one of those guys we got a lot of looks at. Our area scout was ultra-convinced on the makeup of the kid. We got to know him pretty well … the way he competed … blue collar … all of that.

“We really thought we got a mid-rotation guy with that selection. And the way his career started, we were really pumped. He was a workhorse, he threw a ton of strikes, and he had great stuff. After his first couple of years, we were like, ‘Wow, we got a really good pick here.’ In 2008 at Double-A, he sat on a low 2.30 ERA with a 25 percent punch rate. We thought this guy was going to sit in the middle of our rotation for a long time. He had a decent Triple-A year when we moved him up, he got to the big leagues, but he kind of plateaued out. He never had the career that we thought he would.”

Bowden saw action in parts of six big league seasons with the Red Sox and Cubs, appearing in 103 games from 2008-2013.

The flurry of activity concluded a little while later with Boston’s second-round pick – the No. 57 overall selection. And the rationale behind the player chosen – Jonathan Egan, a catcher out of Cross Creek (Ga.) High School – still bothers McLeod.

“I think every scouting director … if you would change things and do them over, we all would. This is one that sticks out with me,” McLeod admits. “We liked Jon Egan quite a bit. I was shooting for upside. We thought this kid had tremendous power. We thought he’d be able to catch. And when you went to watch him, it was a really beautiful swing.

“But what I regret here is that there was another college player sitting there right in our lap. There was a lot of discussion in the room that we should consider him, but my thought process was, ‘We just took Jed Lowrie. That was the safe college guy who performed. Let’s really shoot for some upside here.’ So we ended up passing on Chase Headley and took Egan. That’s one of those that I still to this day look back at. My reasoning did not go with the process. I was shooting for upside when we had Headley sitting right there for us on top of our board.”

Egan played three minor league seasons, peaking at Class-A Greenville in the South Atlantic League. Headley, who went to the Padres at No. 66, entered this year having been a major league starting third baseman since 2008.

While Headley was a miss for McLeod, Pedro Alvarez was the one who got away. A 14th-round pick out of Horace Mann High School in New York, Alvarez opted to bypass the Red Sox’s offer and go to Vanderbilt – and later was the second overall pick in the 2008 draft (by Pittsburgh).

“Missing out on him, we didn’t like that taste – especially seeing what he became,” McLeod says of Alvarez – who entered this year with 153 homers during his seven-year big league career. “It made us want to be even more aggressive going forward in trying to sign those types of players.

“We really loved the kid’s power. We loved the bat speed. He came to our workout that year and really put on a show. We made a serious run at him. I was on the phone a lot with the kid, trying to get him signed.

“Under the old system, the day they show up for class, they’re done. So I’m on the phone with him that morning, and I made a significant offer. Remember, this was the 14th round, and we already had spent a ton of money on the guys at the top. We had our last conversation, and he said, ‘Sorry, Mr. McLeod, I’m here at school now – and I’m getting ready to go to class.’ So we don’t sign him.”

McLeod later found out that Derek Johnson – who was Vanderbilt’s pitching coach at the time and now the Milwaukee Brewers’ pitching coach – was standing next to Alvarez when the prized freshman was having his final conversation with the Red Sox. Johnson was the Cubs’ minor league pitching coordinator in 2013-2015, and his boss was McLeod.

“We were swapping stories about Pedro Alvarez after (Johnson) joined the Cubs, and he says to me, ‘I walked him to class to make sure he got there and that no Red Sox employees were jumping out of the bushes trying to sign him.’”

Looking back at his first draft, McLeod talked about the need to be aggressive and wanting players who could provide impact and upside.

“We knew having all those picks early … we had the ability to diversify the portfolio, so to speak, where you could take some high-impact riskier high school kids, college performers that you felt really good about with athletic upside, and a junior college guy like Clay Buchholz,” McLeod says.

“As history has borne out, it’s probably one of the best drafts of all-time. I’m not talking about the Red Sox. That ’05 draft class was ridiculous in the first round.”

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Chuck Wasserstrom spent 25 years in the Chicago Cubs’ front office – 16 in Media Relations and nine in Baseball Operations. Now a freelance writer, his behind-the-scenes stories of his time in a big league front office can be found on www.chuckblogerstrom.com.