So I know this is a little out of left field, but I was playing around on Trade Machine and came up with this 3-way deal.
Boston
Get: #1 pick, Anderson Varejao, Jarrett Jack, Arron Afflalo
Give: Rajon Rondo, Jeff Green, Joel Anthony, Clippers' 2015 1st Rounder
Cleveland
Get: Rondo, Green, #4 Pick, #12 Pick, Clippers' 2015 1st
Give: Kyrie Irving, Varejao, Jack, 2014 #1
Orlando
Get: Irving, Anthony
Give: Afflalo, #4, #12
The Cavs have to be concerned with the possibility of Kyrie not resigning. In this scenario, even if Rondo walks, Cleveland still received 2 lottery picks, an extra first rounder next year, and a starting SF. Maybe they go for Embiid at 4 and best player available at 12.
Orlando gets the PG they want to put next to Oladipo.
Boston enters total rebuild mode and stocks up on picks. Goes for Wiggins at 1, Smart at 6, and a SG at 17 (maybe James Young or Jordan Adams or Stauskas if he falls)
The C's Roster after the draft could look like:
PG: Smart/Jack/Pressey
SG: Afflalo/Young
SF: Wiggins/Johnson/Wallace
PF: Bass/Sully
C: Olynyk/Varejao/Faverani
The Cavs could put out a lineup of Rondo, Waiters, Green, Thompson, Embiid
The Magic could put out a lineup of Irving, Oladipo, Harkless, Harris, Vucevic