Speaking of Yankees prospects who never really lived up to the hype in the last 25-ish years:
Mike Lowell
Nick Johnson
Jesus Montero
Joba Chamberlain
Jose Tabata - not super hyped but people thought he could one day win a batting title.
Eric Duncan -- man, I read so much shyt about that guy.
Drew Henson
There haven't really been any pitching prospects for the Yankees to have been hyped over.
I mean, Joba was more of a media hype machine than actual scout hype.
Phil Hughes had a decent career and I really think he got off track when he hurt his groin vs Texas (I forget when it happened exactly)
Around the time that Hughes was getting his hype, there were thoughts that Ian Kennedy could be good, but not great. I think he was more of a college star than anything.
Then there was that year when they took Andrew Brackman. I think they drafted him knowing he would need TJ surgery. Or something like that. What a disaster that shyt was.
Brackman went 30th in 2007. High risk, high reward, I guess. Notable guys who went after Brackman include Todd Frazier, Travis d'Arnaud, and Josh Donaldson. All of which could have been great trade pieces or starters for them.
...Giancarlo Stanton went in the 2nd round to the Marlins in 2007, and Freddie Freeman went to ATL. So there's also that.