Monroe to CLE is a great fit obviously. Something like...
CLE trades:
Anthony Bennett
Sergey Karasev
CLE gets:
Greg Monroe
Jonas Jerebko
DET trades:
Greg Monroe
Jonas Jerebko
DET gets:
Arron Afflalo
ORL trades:
Arron Afflalo
ORL gets:
Anthony Bennett
Sergey Karasev
I think DET trading Monroe for Afflalo is one of the more likely trades right now, the question is where ORL would flip Monroe to if they don't keep him and Vucevic together. Yes it may be overzealous to think they'd take Bennett/Karasev over Afflalo/Monroe/other trade return for Monroe - but imagine ORL went into last year's draft with Bennett ranked 1st and secretly praying for him to fall to 2. Chances are despite his start they'd still be drooling. Or even if they had him not that highly rated, they may still be very interested. ORL is tanking because they are thinking UPSIDE. They want stars. If they rated Bennett as a likely star heading into his draft the odds of them still paying a price for him are solid
I personally have a theory that ORL has a specific talent evaluation system that goes after prospects with high fluidity and apparent feel for the game. Vuc, Afflalo, Harkless, Harris, Nicholson, O'Quinn, Oladipo all fit this. Bennett and Karasev both have fluidity and naturalism aesthetically as strengths heading into their drafts.