Interesting conversation.
I would narrow it down to the recruiting classes that contributed to the 1997, 1998, 1999, 2000 and 2001 rosters. Those were some pretty solid years of recruiting, if you look at it from a stand point of the number of players who went on to play professional ball with success. I tend to think that many of those teams under-performed a bit, with the 1998 team actually over-performing.
It has largely been down hill since then, with a slight peak on that downward trend around 2005.