Here's how I see this playing out.
You get the Doc thing squared away. Doc to the Clippers for the 2015 1st. Fine.
There's some concern that submitting KG for DeAndre right away might rustle some jimmies with the league office. Honestly, does it matter if we try to do that right away?
The next step should be dumping Pierce. Preferably to a team like Cleveland who can absorb his salary. Try to get that done by draft night.
Shoot... you could even pursue trading Rondo on draft night if you can land a top pick like Nerlens Noel (very unlikely... Rondo doesn't have that much value at this piont, I don't think)
But at this point... Doc's gone... Pierce is gone. Then you approach KG and see what his mental state is like.
#1 Does he want to return and be a mentor to the youths with a new coach on a lotto team? Great. I'm all for it! ...
#2 - Does he want to leave for a contender? Ok. Give us a list of teams you are comfortable with playing for KG. Is it ONLY the Clippers? Would you be interested in joining the team we send Pierce to? Any interest in joining a team like the Spurs? What's our options? ... See... I have to imagine that the Clippers can't be the only possible destination at that point. If he wants to play and play for a contender, there must be a couple teams that intrigue him. If it's just the Clippers... fine... do the Deandre deal.
#3 - Does he want to just retire? Great. Money off the books. I'm not all that desperate to pay Deandre 10 mil a year for 2 years anyways.
There's no rush to trade KG. We could drag this out to the deadline if we want. There's no "buyout" deadline at the end of the month or anything. We could wait several weeks and try to squeeze more out of the Clippers or get a better package from another team KG desires to play for.