There have been 3 selections by Ainge in which I was irritated the day of the draft
JR Giddens instead of DeAndre Jordan
Fab Melo instead of Perry Jones
Kelly Olynyk instead of Giannis Antetokounmpo
Other drafts I would have gone a different route, but I wasn't irritated (like I would have taken Randle instead of Smart, but I wasn't irritated by the pick)
I think Ainge is a very good drafter, relative to his peers. But the one pick that haunts me is Gabe **** Pruitt over Marc Gasol. There was speculation that the younger Gasol dropped as he would only play in Memphis (he went to high school there as big brother Pau played for the Grizzlies and had grown comfortable with the surroundings as a foreigner from Spain).
The Lakers snatched him up in the 2nd round, traded him for Pau and that led to two titles. It would have been really interesting if Ainge had grabbed Marc Gasol. Maybe the Lakers still acquire Pau, but they may have had to give up Bynum (who was impactful at that time) to pull it off.