One could also easily argue that if Ainge went the youth route, we don't trade a first rounder to bring back Tione and the difference would mean that we wouldn't have made that late season run, so instead of dropping in the draft and settling for Gerald Green (who Ainge was never really a fan of) we would have been in position to draft Granger. Now no one ever knows who Danny would have drafted. I thought Roy was the obvious pick a couple years ago, and Ainge traded the pick for Telfair. I thought Chalmers was the guy to pick this yr, and Ainge picked Giddens instead. It's also been documented that ainge tried to trade up to draft Robert Swift and when that fell through he "settled" on Al Jefferson.
Just for fun I think it would be cool for people to say what they wanted to do dating back to when Ainge took over. I'll go first.
I can't say I knew much about Banks, so I won't comment/criticize that pick. I did like Perkins as a project 2nd first rounder.
I was against the Tione/Raef trade because i didn't like Raef's contract. I was not in the same rush to move Tione, so I would have waited a yr til he was an expriring contract if needed.
I was also against the Battie and Eric Williams for Ricky Davis trade. I thought they held better value. I rooted for Ricky on the C's, but based on what Cleveland was able to swing Battie to Orlando for I still believe we undersold him.
Again I plead a little ignorant on the Jefferson/West/Allen draft, so I won't claim that I knew Jefferson would be great. i wasn't watching too much college ball those days.
I was against bringing Tione back and giving up a first rounder to do it. It brought back a little excitement, but I would have preferred the better draft position and the extra first rounder.
I definitely wanted to make the paul pierce and the #19 for Chris paul trade and Nick van exel's expiring contract trade. Outlaw wasn't a deal breaker for me, but I liked Paul a lot and was getting tired of Pierce (just being honest).
Again i plead somewhat ignorant on the later part of the first round. I knew Granger and Green were the two guys that I wanted, but I didn't really have a preference. I was very happy (after Granger was off the board) that we got Gerald. I didn't know much about David Lee, but I wanted us to trade up in the second round for both Ukic (who knows if he'll be any good) and Monta ellis. Obviously Gomes was a solid second round pick, but not of Monta's caliber. I didn't know of Orien Greene when we drafted him, but liked him a lot in the preseason.
I wasn't for the Scal or Dickau signings.
I thought the Blount/Banks/Ricky for Wally trade was a walking in place trade, so didn't care too much. Ricky had sort of grown on me, so I was sad to see him go, but didn't care too much about the trade.
Brandon Roy was the guy i wanted in the draft, but was fine with Foye or Gay either. i just wanted to take the best player available. I know ainge was scared off a little by Roy's injury history and was leaning towards taking a pg/drafting for need. Mistake imo. I was fine with Marcus williams or the guy Ainge liked (Rondo). Figured we could trade down for either. Also, the AI trade rumors were going on at that time, so that added a lot of drama. I did not like the Telfair trade (especially it being completed prior to the draft). Ainge claimed Telfair was better than any pg in the draft, but I remembered him as the 3rd string pg on the cellar Blazers. It was thought Ratliff would be easier to swing to Philly for Iverson than Raef, but I was scared what we would be giving up for Iverson. When we later drafted Rondo (by trading a future pick who would become Rudy Fernandez) it was thought, we'd be trading Rondo, Jefferson and Ratliff for Iverson. Very glad that trade didn't go down. I watched "Through the Fire" lol, and tried to warm a little to Telfair, but I liked Rondo better. I put up a celticsblog poll (on the older version) asking people who they thought would be a better pg down the road Telfair or Rondo. Obviously i went with rondo, but about 2 thirds to 3 fourths of bloggers chose Telfair. they must have liked "through the Fire" more

I was disapointed we didn't buy the Sergio Rodriguez pick. Truth be told, if you had asked me before the draft who I'd rather have between Rondo or Sergio, i would have gone with Sergio

Turns out we could have had both. A draft of Roy, Rondo, and sergio would have been sweet.
I definitely bought into the tank mode season and had my eyes on durant more than Oden. In my dreams we got the number one pick, but traded down to #2 to take Durant and get something else too (Oden was more desired). I was devastated when we fell to #5. I thought Horford and Conley would be good to, but didn't know what was left after that. i was scared we'd go for Yi at #5. As the draft got closer I kind of liked Brewer and Thornton and had started to think maybe Yi might be ok. The one trade I liked was trading our pick to atlanta for joe Johnson and a later first. I'm thinking that trade didn't have much legs though. i do wonder if we offered the #5 straight up for JJ if the Hawks would have bitten. Assuming we kept the pick, I would have gone with Thorton. I also didn't like how the pick we traded to Phoenix they simply sold and I wondered why we couldn't have just bought it back. I thought Rudy Fernandez would be a great extra pick. I liked the BBD pick and didn't really like the Pruitt pick.
This yr i preferred chalmers over Giddens fwiw.
So I guess if I was the GM, we'd have Chris Paul, Rondo, Sergio and Chalmers as our point guards. Brandon Roy, Monta Ellis, and Rudy Fernandez at the 2. Ukic maybe somewhere. Thornton and Granger at the 3. Jefferson at the 4. And Perk at the 5. Plus whatever we got for an expiring Tione, the draft pick we traded, Tony Battie, and eric Williams. Tons of cap space too(maybe add Camby this Summer or make Presti trades where we take on a Kurt Thomas in order to get a couple more firsts). I feel like Bill Simmons a little too much writing this though. Obviously Ainge either didn't have the desire to go the youth route or got tired of it and scrapped that plan. He kind of only half went the youth route though by keeping Pierce. winning the title this past yr was sweet. Just like Miami was thrilled to bring home a title a couple yrs ago. I do disagree with the premise that we wouldn't have been able to build a title contender. I think we could have been the top young title contender by now imo.