If Portland does try to make a win-now move around Lillard by moving some combination of 3rd/Simons/Sharpe, but keeps Billups, then they are dookie imo.
I am not usually for quick fires, but the way Portland has played these two seasons despite considerable talent is pretty pathetic. They were pretty healthy at the beginning of this season with Lillard, Jerami Grant, Simons, Hart, Nurkic, etc and were still a dumpster fire. That squad should at least have been comfortably above .500 with All-NBA play from Lillard, fringe All-Star play from Grant, and good role players. I hope teams move away from hiring untested great former players with hardly any coaching experience to top jobs a bit.