2010 Draft - here's the grades for the first-rounders, so we can take a look at Vitek as a pick

Harper - 80 Low (only 80 in the book - Moore and Trout are 75s)
Taillon - 70 Medium
Machado - 70 Medium
Colon - 50 Medium
Pomeranz - 65 Medium
Loux - DNS
Harvey - 60 Medium
DeShields - 60 Extreme
Whitson - DNS
Choice - 55 Medium
McGuire - 55 Medium
Grandal - 60 Medium
Sale - Graduated already
Cowart - 55 High
Foltynewicz - 55 High
Vitek - 50 High ($1.359M)
Wimmers - 50 Extreme
Deglan - 50 High
Yelich - 60 Medium ($1.7M)
Brown - 60 Medium ($1.45M)
Cox - 55 Medium ($2M, MLB deal)
Parker - 50 Medium
Biddle - 55 High ($1.16M)
Lee - 60 Medium ($5.25M, 2-sport)
Bedrosian - 50 Extreme
Clarke - Unranked
O'Conner - 50 Extreme
Culver - 50 High
----
Kvasnicka - 45 medium
Sanchez - 60 High ($775K)
Lipka - 50 High
Brentz - 55 Medium ($889.2K)
Lindsey - 50 High
Syndergaard - 60 High ($600k)
Ranaudo - 55 Medium ($2.55M)
Bolden - Unranked
Wojciechowski - 55 High ($815k)
Vettleson - 55 High ($845k)
Walker - 70 High ($800k)
Castellanos - 60 Medium ($3.45M)
Jackson - 50 High
Blair - 50 Extreme
Tago - 55 Extreme ($982.5K)
Ruffin - 50 Low
Olt - 60 Medium ($717.3K)
Jenkins - 60 High ($1.3M, 2-sport)

So, in that draft, does picking at 20, 36, and 39 and coming away with a 50 High and two 55 Mediums qualify as having "really, really hurt our system" and something we'll be paying for for years? I don't think so. Was it the optimal return? Probably not. Compare that with the Angels, who picked at 18, 29, 30, 37, and 40 and came away with a 55 High, a 50 Extreme, a 50 High, and TWO PLAYERS that already have fallen out of their top 31. THAT is really, really hurting your system.

Was Vitek a great pick at 20? Probably not. However, the Sox also got the two supp. picks, a 60 High in Cecchini, a 55 High in Coyle, and a 55 High in Workman. BA ranks the team's 2010 draft as a B, and I think that's a very fair grade. The O's, ChiSox, Indians, Tigers, Marlins, Pirates, Giants, Mariners, Jays, and Nationals are the teams that rank higher, and they split into three groups, ones who hit on high picks (Nationals, Pirates, O's, Indians) and ones who got players later in the first that have panned out well (M's - Walker, Marlins - Yelich, Tigers - Castellanos, Giants - Brown), while the ChiSox and Jays are probably somewhere between. And btw, those are all B+'s except for Washington (A for getting to pick Harper, plus Solis and Cole) and O's (Machado, Bridwell, Klein, Schrader).

So yeah, it would've been a lot cooler if the Sox took Yelich, Castellanos, or hell, even Walker at 20. But don't make it sound like that single pick was so horrible that it was a disaster. It's not like the Royals taking Colon at 4. I'll give you that Yelich or Brown might have been better there, and obviously Walker, but do you want Castellanos there and to not sign Cecchini later? Isn't that kind of a wash?

We could always go back and talk about picks that missed. However, Vitek wasn't the catastrophic pick it's being described as above. Not by a long shot.

Not looking to get into a back-and-forth on this, but to me, you can't really look at the Vitek pick in a vacuum, especially compared to guys who slipped by a lot of teams because of signability. I will give you Yelich and Brown because they signed for comparable money, and I think we're on the same page with Walker where he obviously would have been better but the team can't be faulted too much for not picking him, but I just don't think you can say signing a guy there for twice as much doesn't affect the rest of the draft.

As for other first rounders, I don't recall the Jason Place pick being very popular.