option 2: Rondo is traded for a starting center and we start Smart and AB.
I see this as the best route, but our trade options are limited. The one that probably fits the best would be Detroit. Something like...
Rondo
Wallace
1st rd pick 2015 (LAC)
for
Monroe
Jennings
Butler
Jerebko (expiring deal)
1st rd pick 2015
1st rd pick 2017
Rondo would likely re-sign since it's not a small market and he would be alongside Smith.
We would start Smart, allowing him to further gain experience. Monroe would immediately start alongside Sullinger providing better roster balance. His game, particularly his good passing, seems like an excellent fit in Stevens' offense and would give us a trio of good passing bigs along with Olynyk and Sullinger. Jennings value might be able to be rehabilitated like Crawford's was, which could provide a decent return as his contract would be reasonable (8M) and expiring next season. Butler's deal is not expiring either (2 years left), but at only 4.5M it's also easier to potentially trade than Wallace's would. Plus, Butler has a lot more left in the tank than the running on fumes Wallace. We dump Wallace's contract. We move up significantly in the 2015pick swap, likely from the late 20's to mid-teens, and add an extra 1st pick in 2017.
This, however, can't be accomplished until mid-December because of the restrictions of signed players.
That deal almost certainly will never happen.
1) Monroe is on his Qualifying Offer. Among other things, that means he has "no-trade" power. Why would he want to go to a team that unloads Rondo -- a PG who could probably get Monroe a TON of easy buckets?
2) Also because of the QO, any team that gets Monroe via trade does NOT get his Bird Rights. Monroe is a pure, unrestricted FA next summer. So trading for Monroe gives you NO negotiating advantage towards signing him next summer.
There is literally no reason to give up any significant assets to trade for Monroe when you can -- IF he even wants to come here -- sign him for simple money next Summer.
Detroit has no real leverage. No one is going to give up big assets for a one-year rental of Monroe -- plus he controls where he goes.
If you really want to try to lure Monroe, your best bet is to make sure you have a roster that he will find attractive. For a player like Monroe, the Celtic roster would almost certainly look more attractive with a signed Rondo on it.
Whether Monroe ends up as a Celtic comes down to two very simple things:
(a) Does Danny want him? and
(b) Does Monroe want to come to Boston?
As long as BOTH those things are true, then Monroe WILL be a Celtic next year. If just ONE of those things is not, then he won't.
No trade necessary.
That doesn't rule out trading for him before next Summer - but if so, it won't be by sending any big important assets for him.