I'm just going to say I actually love Ainge as our GM.
He has got us back to relevance and to the 08 title, he has got us coup after coup in draft picks and picked up Coach Stevens who in my opinion is the best young coach in the league. But I think some of his draft history is questionable and even though I would rank him high in the list of GM's in drafting player I think he takes a back seat to; Gar Forman, Sam Presti, Bob Myers, R. C. Buford (in no particular order).
Here is a list of the players Ainge has drafted and players missed.
2003- Kendrick Perkins, Brandon Hunter Missed: José Calderón
2004- Al Jefferson, Delonte West, Tony Allen Missed: None
2005- Gerald Green, Ryan Gomes, Orien Greene Missed: David Lee, Monta Ellis, Marcin Gortat
2006- Rajon Rondo, Leon Powe Missed: None
2007- Gabe Pruitt Missed: Marc Gasol
2008- J. R. Giddens, Semih Erden Missed: Nikola Pekovic, Mario Chalmers, DeAndre Jordan, Ömer Asik, Dragic, Timofey Mozgov
2009- Lester Hudson Missed: Aron Baynes, Wesley Matthews
2010- Avery Bradley Missed: Hassan Whiteside, Lance Stephenson
2011- JaJuan Johnson, E'Twaun Moore Missed: Jimmy Butler, Chandler Parsons, Isaiah Thomas
2012- Jared Sullinger, Fab Melo, Kris Joseph Missed: Jae Crowder, Draymond Green, Khris Middleton
2013- Kelly Olynyk Missed:Antetokounmpo, Dennis Schröder, Rudy Gobert,
2014- Marcus Smart, James Young Missed: (too early to tell)
I know hindsight is 20/20 but I think Ainge has missed more than he's hit on, also I think he may need a big man consult as it seems to be his weakness. Overall like I said earlier he is very good on draft night but I think a few GM's edge him out on talent drafted