I'll be honest, I was never impressed with Doc's coaching until KG, Ray and Thibs arrived. I never thought he was atrocious, but I did think he was below average to average. He was supposedly an offensive coach (and I do think his set pieces coming out of timeouts have, throughout his Celtics career, been very good) but he wisely dopted a defensive philosophy. He was clearly best suited to getting the most out of good veterans, but never really had the opportunity to show that (though you have to say, that division title with Pierce, Payton and Antoine plus a bunch of kids was a good coaching job so the signs were there he'd adjust well to coaching veteran stars).
In hindsight, I have to say he was better early than I thought he was. While guys like Clifford Ray also deserve a lot of credit, he did a good job developing guys like Kendrick Perkins, Al Jefferson, Tony Allen, Delonte West, Ryan Gomes, and Leon Powe. Some guys busted here - Gerald Green, Sebastian Telfair, Marcus Banks - but for the most part haven't done a whole lot since meaning the problem was the player, not the coach (credit to Green for resurrecting his career and playing well in New Jersey the last month or so). I don't think a lot of coaches could handle Rondo so well. He did a good job handling Avery Bradley, keeping his confidence up until Doc was confident he could play Avery. Doc is just good at handling and reaching players, much better than I thought before.
I certainly disagree with Simmons on '08. I don't blame Doc for that strange Atlanta series - as much as it went 7 games, the Celtics won every home game by 20-30 points. They just didn't execute in Atlanta. As for Cleveland, Lebron was at his apex at that point, and I don't think he was as self-conscious about closing games, and seasons, out. But Doc pushed the right buttons, bringing House's energy back when he knew the team needed a shot in the arm, going small when the time was right, and using PJ Brown effectively without wearing the old man down. Not to mention, his use of small ball in the third quarter of Game 4 of the Finals - House, Ray, Pierce, Posey/TA and KG - may have saved that title. The players executed, but he pushed all the right buttons, even subbing in TA, who had no outside shot and wasn't playing a whole lot in that playoff run, for a winded Posey, because he knew he needed to keep a fourth perimeter player out there.
Now, I wouldn't go so far as to say he deserves COY this year. Yes, he's done a very good job, but Chicago has remained on top of the league despite missing the reigning MVP for a good chunk of the season, and Popovich has been, as usual, simply astounding. I'd give it to Pop because I think it's a joke he only has one in his career - a second is well deserved.
Then again, the award is kind of a joke. Pop and Phil have each only won once, and Jerry Sloan has never won it, while guys like Avery Johnson, Sam Mitchell, Byron Scott and Mike Brown have won over the last six years.
As for the actual topic, I'd have a hard time turning down a pick in the 4-8 range for Paul Pierce at this stage of his career. I want him to retire here too, but that's good value. Although, I'd have some fears. Even before the KG trade, I was glad the Cs traded the 5th pick and Wally for Ray. I thought that 5th pick was doomed here because he'd always be "the guy that isn't Kevin Durant." Sort of like Chauncey Billups was doomed from the start, even though he was excited to be a Celtic, because he was "the guy that isn't Tim Duncan." Yeah, Pitino dealt him too quickly, but if Boston fans are honest, they'll remember that they never really took to Billups and given Duncan's immediate success, I have doubts they ever would have. So in this case, whoever the Celtics drafted with that pick - this year, or in a worst case scenario next year - would always be held to Pierce's lofty standards.