"Disasters" seems quite strong.
Trading Toine for Raef was a disaster. The way out of that disaster was trading Raef and 7 for Telfair and Ratliff. Those trades set the team back a few years, and if he wouldn't have been able to swing the Ray Allen trade (which then led to the KG trade), he probably would have been fired after that 08-09 season. Those 2 trades swung fate. He then had several more years of poor moves or a lack of moves, until he finally decided the window was closed (probably a year or two too late, honestly). He was able to work that brilliant trade with the Nets, which again swung fate, but most every move not basically involving draft pick trades, were mostly poor and some of his rumored offers for draft pick trades, let's just say the team is lucky the other team backed out. He royally mishandled the aftermath of the acquiring Kyrie (which was a poor trade at the time and even worse after - and that is not revisionist history you can find the thread, I gave it a C at the time) by not pulling the trigger to actually build a team capable of winning with Kyrie. There was the whole PG13 trade fiasco that was lost because he wanted to want (while Indy didn't). Time and time again, Ainge waited or didn't make moves, and many of the offers that he reportedly made worked out well the other team didn't accept them (the Winslow draft day rumors stand out above the rest, but that isn't the only one).
Ainge did a pretty darn good job in the draft, and he had 3 absolutely homerun trades (Allen, KG, and the Nets picks), but for the most part he was a poor to mediocre trader and his free agent moves were also very hit and miss. Those 3 trades were just so good (coupled with the mostly excellent drafting), they more than made up for the crap that was most of the rest of his moves during his tenure.
