Let's face it, the Celtics are in a tough place right now. There aren't any moves to be made that would bring a star over and there might not be before Rondo's deal is up. Even more problematic is the fact that they have a lot of young talent but none of them look to be superstar-caliber. They have a lot of picks, but none in the immediate future besides their own that could be low lottery level. And they have little flexibility cap-wise until next offseason, though they would lose that if they re-sign Rondo to a max deal.
They need a star to magically become available or Rondo to suddenly be amenable to signing an extension with a team that wants to deal for him. Both scenarios are unlikely.
If they deal Rondo for peanuts or if he leaves, they need to hope the draft yields their next superstar. It would have been nice if that player were already on the roster (if they had gotten lucky in previous drafts with a late steal) but it didn't happen. That means their next best player is not in the league right now and will take 4-5 years from now to develop.
Ainge and management (moved by playoff revenue, no doubt) wanted to delay the rebuild and we're seeing the fallout from that now.
I think the rebuild happened at exactly the right time. The last year of KG/Pierce was bad in hindsight, but Ainge probably didn't get the offer he was looking for until Brooklyn came knocking.
And I also believe the rebuild has gone perfectly since those two were dealt (minus a bit of better lottery luck). Ainge has been super patient and has gotten something out of nothing on a few deals. He has not unloaded his vets for less than his perceived value of them. He will have many chances to make deals this season if the right deals come along. If not we are looking at tons of upcoming cap space. I think the rebuild has been perfect so far.
The rebuild came too late. That's why Brandon Bass' contract is still on the books. That's why Wallace is on the books for two more (the picks were a nice haul but they came with a price). We don't really know what other deals were on the table before for Pierce and Garnett, but I'd rather have something like say, DeAndre Jordan and Bledsoe on the roster now plus a pick than having multiple picks and Wallace's deal. Waiting for those Nets picks to come is fine if you're committed to a long rebuild. They're not so valuable if you're trying to make deals to win now because their value comes too far into the future and with too much uncertainty (nobody knows where the Nets will be those years).
The Celtics were not going to win a title that last year, or even the year before. Better to have realized that sooner rather than later, especially when you sign a bunch of guys to multiple years (Lee, Bass, Terry) in a futile, last-ditch effort. Nobody wanted to see Pierce and Garnett go and at the time, I really thought there was a chance Pierce would play in green his entire career. However, Ainge showed he was willing to deal them. If so, why not deal them earlier?
Yes it did and I totally agree.
Look, hindsight is always 20/20 and belive me, I didn't want to see us ever become sellers and start rebuilding (although I will admit, the final year of KG/Pierce did get kinda painful. We probably should've gotten swept by the Knicks in 2013.)
Plus, I think the job is always to make money and Ainge/Wyc didn't want to turn off ticket holders by dealing the 2 stars of the team while the 2008 run was still fresh in people's minds (including mine.)
BUT looking back, DA probably should've started the famous "rebuild" sooner than he did.
As for when he should've, that's a little harder to say.
You could make a case it should've started in 2010 after they lost to the Lakers in the finals because looking back, that truly was legitimately the Celts last real shot at winning another title.
You could also make a case it should've started after the 2011 season. Granted, maybe the Celts beat Miami that year if they hadn't dealt Perk and/or had a healthy Shaq (and healthy Rondo for that matter.) But after that season, it became emphatically clear the torch had been passed in the East from the Celts to Miami (more specifially, Lebron.) The problem however, with doing the rebuild that summer was everyone knew a lockout was coming so if DA tried to dangle Pierce, Ray and KG for trades, who knows if anybody would've agreed to a trade based on the uncertainty of the lockout and whether there was going to be a 2011/12 season.
Finally, the rebuild should've definitely began in 2012.
Yes, the Celts had a magical playoff run, but looking back it was as much about luck as anything else (remember Chicago lost Rose and Miami was without Bosh in games 1-4 vs the Celts which also made a huge difference.)
After Ray decided to leave the team (and take less money for Miami) it should've helped make things clear that it was time for Ainge to move on. He could've dealt Pierce then and NOT have resigned Bass and Jeff Green (along with picking up Courtney Lee and Jason Terry.)
The summer of 2012 was DEFINITELY the time to do it and DA began the rebuild one year too late.
Again, hindsight is always 20/20