Ainge hasn't drafted well since 2007. He has some ok players (and the 2 best are hurt all the time in Bradley and Sullinger), but hasn't hit a home run since Davis in the 2nd round of 2007 or Rondo in the 1st round of 2006 (powe was in the 2nd round in 2006 as well). Even 2005 with Gerald Green wasn't a great pick in retrospect, but that one was a virtual no brainer at the time so I can't fault him there (and Gomes and even Orien Greene were pretty solid 2nd rounders). 2004 was a monster draft with Jefferson, Allen, and West and even the 2nd round pick Reed played 136 games in the league (which isn't bad for a mid 2nd rounder).
I mean seriously since Davis in 2007 Ainge hasn't hit a homerun. Bradley looks like a good pick, but he has missed a ton of games due to injury, which is also the same for Sullinger so you can't really call them home runs, though I think they are probably solid doubles. Erden was a solid pick with the last pick of the 2008 draft, but considering how quickly we shipped him off he was also far from a home run.
And Ainge also traded away a lottery pick in 2006 for crap i.e. Telfair. Wasted pick. Obviously trading the lottery pick in 2007 for Ray Allen worked out quite well especially since that lottery pick is currently on Boston.
Ainge brought Boston a title with the Allen and KG trades, which were both precipitated by the moves he had made when he first took over, but quite frankly he hasn't been a very good GM since the summer of 2007. He has no great draft picks, no great trades or free agent signings, and it doesn't appear the team is realistically close to a title nor will be any time in the next 5 years. Ainge is getting awfully close to Joe Dumars territory i.e. the savior that turned into a goat very quickly.