WARNING: a lot of posts while I wrote this novel below, so I am a bit redundant.
The context of the whole DA evaluation since he got KG and Ray should be seen in how he filled the three main roles: backup big, backup wing, backup PG. Since we won in 2008, we give him a pass. But he really could have done himself a favor signing Posey for three years at the time, we'd be in Posey's final year now and would not have had to think about that spot since.
1. I don't think Nate has done a bad job. His role is to backup Rondo, and as expected we've shortened the bench in playoffs and really TA has seen almost all the bench minutes at 1/2/3 with Finley. The reason is they are more useful in this series and are playing better. If Rondo misses a game, I'll be thankful to have Nate over Eddie House.
2. I think not getting Chris Anderson was a huge deal. I have to think he could have been gotten with an aggressive push, a three year MLE. Having a big rotation of Perk / Anderson at C and BBD / Powe at PF would have been huge. You cannot overstate how much better Anderson is than Miki Moore, PO'B, and Sheed. As an added bonus he'd be going into his final year, instead of having two more. Instead they danced around with Maggette and Posey.
3. I do give minus points for DA resigning Tony Allen, and drafting JR and Walker, and then having a coach that played none of them and instead relied on House as his primary backup wing. (Read that again and say ugh to yourself.) I think primary wing/guard backups of Tony Allen and looking for a midseason pickup to augment (altho Marbury didn't work) wasn't a bad plan. Just something the coach of the team wouldn't go for. It's DA's team and coach - not having them on same page hurts.
4. They could have gone after Grant Hill first with the MLE and then chased big men left on the market (or waited in season to resign one.) Would they have been worse if the big rotation had been Perk / Sheldon and KG / BBD / Scal? Resigned Powe and hoped to get a boost mid season?
In summary - I think he never got a big move to secure some talented depth and consistency. I guess big man didn't look like a big issue with Perk, BBD, and Powe around KG, but that's been the nagging problem more than the wings in my mind. In the playoffs Pierce, Allen, and Rondo play enough minutes that the wing roll is really reduced. What DA failed to do is get a wing that Doc trusted enough to play consistently during the regular season for 2008/9.
Here's my hypothetical:
DA signs Posey to a max MLE deal for three years in 2007. (Assume no 'I got my money, now I'm lazy' type drop off, Posey being on a one year deal may have kept him motivated.) In 2009/10 he'd be our Finley, older three point shooter second wing. In 2008 he signs Anderson as the fourth big with a three year MLE type deal. Resigns House and Allen. Sells his first round pick (instead of drafting JR) and buys Walker.
Perk / Anderson / BBD
KG / Powe / Scal
Pierce / Posey / Walker
Allen / Allen
Rondo / House / (Marbury at mid season)
This team doesn't get by CLE without KG (probably) but gets by ORL. Don't forget that Powe went out against CHI - the team DA had that year probably gets by ORL if Powe doesn't get a flat tire.
The big payoff is this year, coming into the season they'd have:
Perk / Anderson
KG / BBD / Scal (assume Powe still gets hurt, etc.)
Pierce / Posey / Walker
Allen / Allen
Rondo / House
Instead of adding Rasheed for 2011 and 2012, they can play out the string with about the same team and a lot more flexibility. How much better is a team with Anderson instead of Sheed? Hard to say. With a bigger wing that could shoot in Posey, they'd have had more options in who to bring in as the backup guard.
At the end of the day - that's probably not enough to change the fortune of the team. I think they spend a little more money on salaries up to this point, but without the bad Sheed deal. They probably also get a few more home playoff games. And that's DA's real challenge. He can't effect the team much without taking out one of the starters - and doing that will almost certainly make the team worst before it gets better. I'd give him a B for everything since KG was picked up, since 2007, maybe a B-. Not sure that was a way for him to get an A.