It's amazing how fickle things like "drafting ability" can be. Danny’s been the C’s GM for 15 years now, and in that time it seems like his reputation went from good drafter, to bad drafter, to great drafter.
If you asked me, in his first 5 years, I thought Ainge drafted pretty well, especially for a team that was mostly drafting outside of the lottery. Now he didn’t hit any grand slam home runs, didn't nab any All-NBA/All-Stars in the 2nd round, but he had a couple big hits in Big Al and Rondo, and a lot of solid if unspectacular picks with the rest, many of which he was eventually able to flip for value at some point. To me the only whiffs were Marcus Banks and using #7 to trade for Telfair, the rest were good moves. I considered this a good 5 year stretch for Ainge:
'03-'07: Trying to rebuilding around Pierce yearsHits Misses Kendrick Perkins Marcus Banks
Al Jefferson #7 for Telfair
Delonte West
Tony Allen
Gerald Green
Ryan Gomes
Rajon Rondo
Leon Powe
Glen Davis
#5 for Ray Allen
But then once the C's assembled the championship team for '08, Ainge didn't seem to do so well. Definitely had a solid hit in Avery Bradley, and Sullinger contributed all 4 years even if Ainge was unable to get any value for him in the end and was lost for nothing, but now the hits seemed few and far in between. Suddenly he wasn't getting those consistent solid hits in the late first rounds like he did when the team was rebuilding, nor was he nabbing any rotation players in the 2nd. Not only was he not drafting good players, but he was missing out on great players, studs like DeAndre Jordan, Jimmy Butler, Isaiah Thomas, Draymond Green who were all available near where Danny was drafting. This hurt his reputation too, passing up studs to draft duds. More misses over the same number of drafts with fewer picks. Maybe Danny wasn't really a good drafter, and just got lucky over his first 5 years?
'08-'12: Big 3 EraHits Misses Avery Bradley JR Giddens
Jared Sullinger JaJuan Johnson
Fab Melo
Then the C's enter a new rebuilding era with Stevens, and at first, Danny's drafting looks a little murkier here. Guys like Olynyk and Smart were okay where they were drafted, and while Olynyk was lost for nothing he did help win a playoff series coming up huge in Game 7 vs. Washington. He was a solid contributor all 4 years, and the same can be said for Smart. They weren’t duds, but it’s hard not to look at Olynyk and not think about how the C’s could have had Giannis, while at the same time wondering if Smart should be brought back and will be worth his next contract. While not whiffs, these picks weren’t helping his reputation as a drafter. Then it seemed like a lot of busts and question marks: James Young was a bust. RJ Hunter was a bust.
The Rozier pick was (now infamously) given an F. Danny tried to trade 4-6 picks for Justice Winslow, he picked Jaylen Brown about 5-6 spots too high, he failed to flip players or picks for Noel or Okafor, he passed up a generational talent in Fultz to draft Tatum, who trades out of the #1 spot? He let Josh Jackson’s reps bully him into drafting somebody else. In between the ’16 (Brown) and ’17 (Tatum) drafts, Danny’s reputation has a drafter still hadn’t been repaired.
As of now though, Danny looks like a genius again. The recent picks that were criticized, now look like gold. Rozier has ascended to meme status, Brown and Tatum look like studs. Others laughed at Danny, but now Danny's the one laughing.
'13-'17: The Golden Era of StevensHits Misses Kelly Olynyk James Young
Marcus Smart RJ Hunter
Terry Rozier
Jaylen Brown
Jayson Tatum
(With Yabusele and recent 2nd rounders too soon to tell).
All this to say, I think it's interesting how Danny's drafting reputation has been all over the place, especially how it seems to have flipped recently. Solid in the first 5 years, disappointing in the contending years, and it didn't look good at first during the Stevens era, but now it looks great. Still it could swing the other way again (Fultz could have an MVP season, Rozier comes back to earth and is lost for nothing, Brown and Tatum's career trajectory starts to look more like Michael Carter Williams, etc.). But for now, it's nice that our GM looks like a great drafter again. In Danny I trust!