2. The Trail Blazers swap stars with the 76ers
The Potrland Trail Blazers are probably better off going the fire sale route if they do indeed have to trade Lillard this offseason. However, teams can be stubborn and look to hold onto a perceived title window, even if it is not the best thing to do.
There are two reasons why the Blazers could do this. First is pressure from ownership that does not want to fall into irrelevancy. This is especially important in a small market like Portland. They want to sell ticktes.
The other reason why the Blazers could do this is the GM Neil Olshey trying to save face. If he can get another star in return he might be able to save face and keep his job longer, whereas if he has to trade Dame the team could just punt on that entire operation and start anew.
Thus, I would not completely close the door on a superstar swap for Philadelphia 76ers star Ben Simmons. Simmons definitely is not as big of a superstar as Lillard and while it might make no sense for Portland, he still is viewed as a star that can give Portland something to “still win” after trading Lillard.
The deal could be something along the lines of:
While most basketball fans would agree that this does not move the needle for Portland, ownership and the GM can pass this off as a star swap where they get the younger star in hopes of fixing Simmons’ jumpshot.
As far as Philly is concerned, they get exponentially better by adding Damian Lillard. The offensive possibilities with Lillard and Joel Embiid would be extremely special and with a good defensive unit around them, Philly could be the team to beat with this kind of trade.