How about the following?
Rondo
Green
for
Monroe (via S&T)
Jennings
Rights to their #1 pick (they would be selecting for us)
Why for us? Monroe gives us much needed size and is still just 23. Jennings has a reasonable contract (8M over the next 2 years) and I think he could flourish playing under Stevens. He too is very young (24) and if nothing else, his value could improve, much like Crawford's did. Right now their #1 is projected to be #8. Draft Express has Saric, Harris, and Gordon available at the spot, while Chad Ford has Smart, Harris, and Saric. All in all, this gives us young talent throughout our roster (Monroe, Sullinger, Olynyk, Jennings, a potentially re-signed Bradley, our lottery pick this year, the #8 pick, and #17.
Why for them? The trade allows Smith to move to his natural 4 spot, while giving Drummond the opportunity to carry more of the offensive load on the inside. Green rounds out their ultra athletic frontline and provides spacing with his ability to shoot. Rondo is a definite upgrade over Jennings and will be able to create easy scoring opportunities for both Smith and Drummond. All they need to round out their starting lineup is a sharp shooting SG to help space the floor. Perhaps Caldwell-Pope develops into that or maybe that need is addressed via free agency.