And while you don't make moves in retrospect, you certainly critique them. Danny is batting below the Mendoza Line with his moves since winning back in '08.
I *hated* everything about the 2008 off-season. Danny really dropped the ball, I think.
People don't understand how much of a killer that off-season was. I didn't understand it. At one point, there was one side of me that Ainge didn't feel like the team was going to contend after 09 and absolutely no later than 10 - so he didn't want to committ long term (Posey.) But then as we saw, the team basically was a contender through 2011. However, at the same time - he was willing to offer a 5-6 year deal at the full mid level to Corey Maggette (6M per.) that contract would have been awful!
If Danny had a good off-season in 08, got us even one contributing veteran in the front court - that team could have EASILY repeated. The 2009 team had a far superior starting 5 to the 2008 team. KG dipped a little, but was still the dominant KG on the defensive end and on the boards. Ray rebounded from 2008 (which was actually Ray's worse year here.) Pierce was still Pierce. And Rondo and Perkins improved dramatically from the 08 title team. If Danny had replaced PJ Brown and Sam Cassell (not the 08 Sam Cassell, but the Sam Cassell that we thought was gonna give us - a solid veteran back up PG), that team would have won it all, but most importantly it could have saved KG's career. That was a real carryover to 2010 because KG in 10 was really subpar. If we had a healthy KG in 10, hell even the 2011 KG - then we beat LA. Game 7 was lost on one simple stat: 18-3 (18 rebounds for Gasol, 3 for KG.) This was all tied back to that (non) off-season Ainge had in 08.
The 2009 off-season (before the '09-'10 off-season) wasn't a bad one, in my mind. Signing Rasheed Wallace and Marquis Daniels seemed like a coup at the time. The results weren't even bad; Rasheed played his heart out in the 2010 playoffs, and was a big part of us reaching Game 7 against the Lakers.
Sadly this is Ainge's best off-season. Signing Sheed, who was a huge bust up until the playoffs. And even in the post-season he wasn't *that* good. For every big shot he made (Game 6 against Cleveland) - he was utterly horrific on the boards in Game 7 against LA. He didn't crash at all. And even his laziness -> (hell first play of the game after Fisher's missed outside shot, he tried slipping away into the front court rather - which cost us a rebound and Fisher made a 3; was like that all game with him)
2010 was another off-season where there was very little criticism at the time. JO, Shaq, Delonte, and Wafer all seemed like good adds. It was looking brilliant early on, too, but injuries derailed us.
He signed injury prone players. They knew JOs knee was killing him in that 10 playoff series we had v Miami. Jermaine never even got surgery on it. And we gave him the full mid-level. Just imagine if we split that mid-level on say Matt Barnes, and someone else. With Barnes (the back up SF that we needed) - we don't make that Perkins trade, and we would have had the defensive wing we needed for LeBron-Wade. As I said in my original post; Shaq was a great signing. But we got so enamored with him that it eventually cost us -- thinking he was going to be healthy.
Also, that off-season we lost Tony Allen. Ainge loses huge points there.
Finally, this off-season was another solid one in my mind. The Baby-for-Bass trade looks great, we'll see on Wilcox, Dooling appears solid, Marquis is contributing, Pietrus should be a good addition, etc.
It all comes down to resources. With the very limited money that Danny has had at his disposal, I think he's done pretty well, with the exception of the summer of 2008.
I think this off-season has been good given that Ainge had no flexibility because he wanted to keep the cap space for 2012. Dooling isn't that bad as people say. He's a good locker room guy and I'd like to have him back at the min. We also picked up a bonus (protected) 2nd rounder in that trade. Not sure I'd want Dooling as my primary back up PG moving forward tho.
But anyways, in all of your off-season breakdowns - you never mentioned the drafts. It's been 4 years and we haven't come away with an impact rotation guy since Baby.