One of the issues Portland is having, is many teams want Holiday as an upgrade to their PG depth chart. Most of the contenders will need to trade one of their current PG's as part of the deal. Portland does not WANT another Guard. It will likely take a third team or trade to a non-contender to bring Portland a forward for holiday.
I think it will most likely be a three team deal.
Two frameworks that make sense:
PHI sends Harden, gets Jrue
LAC trade Powell, Morris, get Harden
POR trades Jrue, gets picks from each team
BOS sends Brogdon, gets Jrue
LAC sends Morris, gets Brogdon
POR trades Jrue, gets picks from each team