It will be very interesting to see how things play out in Portland. If Lilliard stays more than likely Simons is gone, as his salary is a natural fit to trade for another position of need now that they have a glut of talented guards in Sharpe and Scoot. Simons is an excellent player in his own right, but is whatever he get can get in trade to fill a position of need, is that enough for Portland to be a contender to satisfy Lilliard? I have my doubts. Sharpe and Scoot would need to grow up fast to fit Lilliard’s short window, though I’m a huge believer in Scoot can make immediate big impact, but he also brings a little redundancy with Lilliard there.
It’s a tough situation for Portland as they seem they want to try to make it work with Dame. Me personally, I’d trade Dame for package of young assets, and let Simons, Scoot, and Sharpe grow at their own pace along with whatever they get for Dame. Simons can play the 1 or 2 and is a nice fit along the better defender in Scoot, or playing the 1 fitting in with Sharpe. Would be a nice 3 guard rotation for the future, and you may be able to play all 3 at once at times too.