I don't think the Blazers would trade Lillard without unloading a bad contract with him. Sort of take your pick with those, Meyers Leonard, Evan Turner, or Mo Harkless. All have bad deals. I'd take Turner only because he has some PG skills and might be able to play PG for the 2nd unit with someone like Okobo while he's learning the game. His size allows for us not to have flashbacks of the dual PG sets of Hornacek days.
Probably take Jackson, Warren, Chandler, and Dudley to make it all work, for Lillard and Turner. I think I'd do that trade still.