When it comes to the Celtics, I'm in the Championship or Bust camp. I'm a giant KG fan, but if the team doesn't have a good chance of winning this year or next as presently constituted, and Ainge can't fortify the roster to make them more competitive, I would support a trade for assets.
Everyone talks about how DA was in favor of Red trading Bird and McHale at the end for Person, Schrempf and Sam Perkins. If Red made those moves, maybe the team doesn't plunge into a decade of despair. Red chose to trade a lesser asset, Ainge, to bring in two bigs to help fortify the Big 3 for another run, and it didn't work.
In the NBA, top of the league talent wins title. In almost every case, that kind of talent comes to a team through the draft, (with the three "ensemble" champions, the Mavs, Cs and Pistons, being the outliers) or unrestricted free agency, in LeBron and Shaq's cases.
Boston doesn't seem to be a place that can snag a top five player through free agency. The best chance for the Cs to rebuild into a championship team is to garner as many assets as possible, by using their most trade-able assets now. If that means winning only 36 games this year and missing the playoffs, instead of winning 44 games with KG and PP and being dispatched in 5 games by Miami in the first round of the playoffs, that's OK with me.
Maybe the ping pong balls finally go this team's way (the Cs can send the team doctor to the drawing). Maybe one of the acquired young assets, like a Bledsoe or a Harrison Barnes, becomes a breakout player.
A whole new generation of Celtics fans have tasted success. They're not going to want to see the team wallow in the middle ground for a decade or two like the last time the Cs brass chose not to trade off legendary pieces of a fast fading dynasty.
Also, I'd like to see Pierce and KG play for another title in their final years. I thought it would have been in Boston, but the gods have been quite unkind to this team regarding injuries ever since Pierce's miracle recovery out of the wheelchair in 2008. Pierce on Golden State, trying to push that team and their rabid (and deserving) fan base over the top, would be fun, and KG on my second team, the Clippers, would also be good. Getting the Clippers over the top, marginalizing the Lakers in LA, would be an added benefit for Celtics fans