Humphries and Lee for Boozer and the Bobcats pick could work if Humphries and Lee show some value during the start of the season. The Bulls would gain some flexibility by the end of the season, with Deng and Humphries expiring.
But the Celtics only commit to Boozer's ugly contract if they're getting the Bobcats pick. It would also mean Bass should be moved, because there would be no minutes for Sully and Kelly behind Boozer, who would start at PF and is undersized to play C.
If they did this trade, then move Bass+Crawford to OKC for Perk+PJ3+Dallas 2014 pick, the C's could have 25M in expirings in 2015, or maybe use those contracts a la Ratliff.
Rondo/Pressey
Bradley/Brooks/Bogans
Green/Wallace/PJ3
Boozer/Sully
Perk/Olynyk/Fav/Fab
That would mean being an 7th-10th seed in the East, and having two more 1st round picks, possibly in the lottery.
2014 own/Nets/Bobcats/Mavs
2015 own/Clips
2016 own/Nets
2017 own or Nets
2018 own/Nets
The Bobcats pick could be in 2015 or maybe unprotected in 2016
The Dallas pick is top 20 protected, so it'd probably end up in a 2018 unprotected (just like the Nets) pick.
Eleven first round picks 5 own, 4 unprotected, 2 protected in five years are a lot of trade chips.