Stay with me for a second...
Whiteside, Simons & a 1st Rd Pick for Dieng and Covington really sets this team up moving forward, assuming Jody Allen is all in and willing to pay the tax. The Blazers pick up the Ariza option (if he pans out the rest of this season) and resigns Melo. They would be short a backup PG, but they can find someone for cheap as Lillard or McCollum would always be on the floor.
I am not a Simons fan so I make this trade, but I know most of you are a fan and would not make this trade. That bench is pretty decent. Maybe the Blazers sign Napier again.
PG Lillard / Napier
SG McCollum / Hood / Trent Jr
SF Covington / Ariza /
PF Collins / Melo / Little
_C Nurkic / Dieng
I would make that move if the pick is for 2021 and Lotto Protected. If MIN wants our 2020 pick, I would insist on Little rather than Simons.
The deal should include Napier, then we resign him this offseason. He is a better player than Simons at this moment (This will attract argument, but Simons has putrid advanced stats. He will end up better than Napier, but its years off IMO), so even the 3rd piece in this trade would be a better immediate on court contributor than the main value we send out. That's the sign of a really nice win now trade.
We would have bird rights if we obtain him via trade, unless I am mistaken. Give him a 2 year / 10M deal and draft a combo guard for the future.
Assuming we keep out FRP and still miss the playoffs after this deal, we would have pick 13/14. I am obsessed with
Josh Green (Wes Matthews / Josh Hart hybrid) and ideally we take him to develop into the type of glue guy that we now have at SF. I also think Gary Trent is better at SF than SG, he has the mass to guard the big SF moreso than the footspeed to guard SG. So I move him down to 3rd string SF. With our own SRP, I like the idea of a PG to develop. There are a gaggle and I actually am not a Ducks homer, but I like
Payton Pritchard as a try-hard backup PG prospect. Elite shooter who can run a team and isn't a great defender but puts in effort.
G - Damian Lillard / Shabazz Napier / Payton Pritchard
G - CJ McCollum / Rodney Hood / Josh Green
F - Robert Covington / Trevor Ariza / Gary Trent Jr
F - Zach Collins / Carmelo Anthony / Nassir Little
C - Jusuf Nurkic / Gorgui Dieng / Vet Min FA
That is one heck of a roster IMO. Really gritty, enough offense but very improved defense. Actual backup PG. Young depth at each spot but littered with vets as well. I think that roster could win a championship, it has a lot of similarities to the Dallas 2011 roster IMHO.