I thought it would be fun to look at the 2002 through 2007 drafts to imagine what might have happened in the first rounds if Neal Huntington had been in charge rather than Dave Littlefield.
The temptation here is to just look at the players who would have been available and, you know, pick better ones, but I'm going to try not to do that. Instead, I'm going to rely on my memories -- which might be faulty -- of what happened and how prospects were perceived at the time. Therefore, I won't have the Pirates taking Tim Lincecum or Clayton Kershaw in the 2006 draft, even though those players were regarded as top talents, because I simply don't think Huntington would have taken them.
One pick I'm not sure of is Andrew McCutchen in 2005. Huntington might well have picked someone else. I'm just not sure who. You can argue about that one in the comments.
With his first draft pick, Huntington would have taken a risk on the higher-upside high school player. Of course, that assumes that college pitchers aren't risky, and we now know that isn't true. Anyway, the Pirates certainly would have gotten a better player, but Upton would have been treated as a villain in Pittsburgh if he had played there as he has with the Rays.
I don't think there's any way the Pirates would have taken Maholm, whose upside at the time of the draft was, well, something like what he actually turned out to be. Instead, I think they might have taken Aubrey, a top college slugger who went three picks later to Huntington's franchise at the time, the Cleveland Indians. Aubrey posted good numbers in the low minors before his career was undone by injuries. He had a couple cups of coffee in the big leagues and is now a Class AAA veteran, having played in the Indians, Orioles and Nationals organizations in the past three years.
There's no way Huntington would have cared one iota about Walker being from Pittsburgh, and instead he would have opted to throw money at one of the two top talents still available, either Weaver or Stephen Drew. I'll go with Weaver in this scenario because both Upton and Aubrey are hitters. Weaver was selected by the Angels one pick after the Pirates selected Walker, and Anaheim paid $4 million for him. Obviously, that was money well spent -- Weaver is a workhorse, and a really good one.
Actual pick (11): Andrew McCutchen
New pick: McCutchen
Actually, I'm not sure what Huntington would have done here. Someone like Chris Volstad, who has that archetypal pitcher's body that Huntington loves, might have been a possibility, but I'm not sure what Huntington would have thought of Volstad's underwhelming stuff. Also, Huntington's Indians took Trevor Crowe, who hasn't done a whole lot, at No. 14. Ultimately, though, Huntington would have found much to like about McCutchen, so I won't change the pick, even though that might be overly generous to Huntington. The Reds took Jay Bruce one pick after McCutchen, and Justin Upton, Alex Gordon, Ryan Zimmerman, Ryan Braun, Ricky Romero and Troy Tulowitzki were already off the board when the Bucs picked. This was a really good draft.
Many analysts regarded Miller as the best player available in 2006. He was 6-foot-7 and left-handed, and the Tigers ended up signing him to a contract that guaranteed him $5.45 million. In other words, there's virtually no doubt the Pirates would have picked him if Huntington had been in charge, even though Clayton Kershaw and Tim Lincecum were still on the board. It might have worked, too, if Miller had gotten to spend his minor-league career in a patient organization rather than with the Tigers and Marlins, who at the time were two of the most schizophrenic teams in baseball when it came to the way they treated their prospects.
Actual pick (4): Danny Moskos
New pick: Matt Wieters
This one is even more obvious, as nearly everyone thought Wieters was the top available talent when the Pirates picked. Wieters still hasn't become a superstar, but he quietly became an excellent starting catcher last year, and that's more than the Pirates are ever going to get from Moskos.