Everything posted seems so recent to me, although kind of amazing that moves in '07 (Ray) and '11 (Perk) seem recent.
For me, Danny came in and and pretty much immediately traded Antoine away for scrubs. Antoine was 26 and a 3x All-Star. I was okay trading Antoine away, but if you do trade him, then you have to get back another All-Star or a top-3 pick, not Raef Lafrentz.
Then a couple of months later he traded away Eric Williams and Tony Battie for Ricky Davis. Ricky Davis!?!? The dude who played for the worst team in the league and tried to shoot at his own basket to get a triple double? Eric Williams and Tony Battie were the heart and soul of the team, kind of like Kendrick Perkins and James Posey were to the KG-era C's. On top of all that, Ainge traded them away during a 5 game win streak (and 5 game win streaks were pretty rate between the Bird and KG eras). I believe the trade led to Jim O'Brien quitting.
But then, amazingly, I fell in love with Ricky Davis. Dude played hard all of the time, and I believe Doc once said he'd run through a brick wall if Doc asked him too. He was definitely fun to cheer for, and even had the Get Buckets Brigade, a whole section he bought season tickets for,
did a lot for the community too. But then Danny traded him away for Wally Szczerbiak!? My heart was ripped out a little at that point. And of course the C's missed the playoffs that year too, and I just knew if they kept Ricky they would have been able to turn things around and make the playoffs (despite the fact that the C's had pretty much the same W/L% before and after the trade).
Really questioned the Ray Allen move too, but after the KG trade (and seeing how all those other trades I hated led to the KG trade), I now always give Danny the benefit of the doubt.
But those moves in his first few years, before he earned my trust and the league wide reputation as one of the best GM's, I definitely hated some of Danny's moves in those first few years.