I think Detroit is a good trade partner for Rondo because you can fashion deals around Drummond (my preference) or Monroe, two blue chippers.
One of the problems I see is that there aren't a lot of other teams that match up well. The one other team I would look at is Charlotte, for three reasons: (1) they are looking to improve in the short term (see, e.g., Jefferson signing); (2) they are aware that they have trouble attracting free agents and that when they do they have to overpay (again, see, e.g., Jefferson signing); and (3) I don't think they are particularly shrewd.
Proposed trade:
CHA receives: Rondo, Wallace (post Dec. 15), Bass, and Lee
BOS receives: Kidd-Gilchrist, Biyombo, Sessions (expiring), Gordon (expiring), 2014 1st round pick from Portland, 2014 1st round draft pick from Detroit, 2016 first round pick.
Charlotte has been looking for a signature player for that franchise, and Rondo would certainly be that. Also, I think they'd be intrigued by a Rondo/Walker/Jefferson/Zeller core.
For Boston, that's a lot of assets and a lot of cap space.
pretty similar to a trade I have been proposing for a long time on this board. I think Ainge does something like that without giving it much thought.
This. I understand the one-building-block-to-zero concern, but this trade would free you up to do pretty much whatever you want. Your roster is Jeff Green, young assets at every position, and expiring contracts. You have tons of cap space going into a nice FA class if you choose to go that route, and you have a treasure trove of first round picks including four in what projects to be an absolutely loaded draft.
Any rebuilding team would kill to be in that position.
First, it isn't a particularly great FA class because it lacks players of consequence who would consider a rebuilding team. You probably end up with someone who isn't even as good as Rondo.
Second, the team won't be able "to do pretty much whatever you want" because most useful moves require others to agree to them, whether it is trades or FA signings. History shows pretty clearly that bad teams get overpriced, underwhelming free agents. Wade attracted Lebron and Bosh. Harden made Houston make sense to Howard. Rondo is our best shot at a decent FA pickup.
On the other hand, I like the Portland 1st and the Charlotte 1st. Both have a good shot at the lottery.
When I said "do whatever you want", I was implying versatility, not omnipotence. You have the cap space to sign free agents, the assets to make trades, and the picks to simply draft quality talent.
I agree that you're probably not finding your building block in 2014 free agency unless something ridiculous happens. All of the guys young enough and good enough to head a rebuilding project are RFA's, and with the possible exception of Cousins their teams aren't letting them go. But as long as you don't talk yourself into giving a fat contract to a lesser player just because you can, that cap space won't just go away.
But 12 first-rounders in 5 years can make things happen. Consider that the Pelicans pried Holiday from Philly for Noel (a #6 pick in an unimpressive draft) and a 2014 first (not as good as you think, since the Pelicans have a competitive roster now). Whether you use the picks or trade them, having all of those picks is a fantastic position from which to rebuild. That's not even mentioning all of the young, cheap talent you'd have on the roster after this trade.