The Blazers have assets to make a trade for a good, young, big Small Forward. It'd be great to add talent right now and see what the core will be moving forward. It would also be nice to add a third piece that is deserving of a future salary and not an overpay. (Think Nicolas Batum). I really like the idea of Trey Murphy III. I don't know if he'd be available but the Blazers have the means to make a very good offer. My stance is that it's very very hard to replace a very good fit that might be available now (like Draymond Green when he was drafted) and hope you get something in the future. It hasn't worked out for the Warriors with some very high draft picks. If there is a player the Blazers could get now that could form a very strong core, I would like to "go for it."
Next summer Portland has 7 usable 1st rd picks available to trade. In theory, give Chicago the GSW 1st to satisfy that trade, draft the Blazers 2024 pick with the agreement to complete theoretical trade right after the draft, and also then have the Blazers 2025, 2027, 2029, 2031, Bos 2029, Mil 2029 picks. Not all 7 are likely needed to make any deal happen, but there is a chance to make a real splash next summer. Add in Simons, and Brogdon's exp salary, and you have 7 draft picks and 50 Mlion in salary assets. If Jaylen Brown is still angry next summer, Luka, OG Anunoby S&T, Zion, etc.. Getting hopes a little too high, but... The Blazers have a real future. Crazy.