The tough part in a deal with Portland is getting the money to match, this would be complicated as fuck.
Just theoretically
Siakam + S&T Jakob + 13
For
Simons + Nurkic + Sharpe + 3
Works cap wise.
There might be some other iterations that work once each team sorts out it's cap holds (both teams have a bunch of free agents), but I've got nothing.
We get a lot worse, but it would be a flash rebuild with Scottie and an elite prospect (Scoot?) at the 3 spot. Sharpe and Simons are nice, nice young pieces too. S&T Gary & Fred for the best we can get for them and play the kids.
I generally prefer the whole "stay the course" and be patient bit. But if you're given an opportunity to add 2-3 young pieces with pretty significant upsides, you have to strongly consider it. Scottie & Scoot (Scooty?) would have elite tandem potential. Simons is turrible defensively but if he ever even becomes average is a really, really nice modern shooting guard...but right now he's a 22 million dollar anchor if Portland really wants to contend and I'm a Shaedon Sharpe stan. I think there's stealth superstar potential there. He would be a must get from the Blazers for me.
Portland maybe does it or similar because it turns Simons and Nurkic's money into an all nba player and hyper efficient C that is a pretty solid 2 way step up from Nurkic. Allows them to then use their bird rights on Grant as a 3rd scorer. Go and get a defence 1st 2-3 who can shoot and that's a contender in the west if you squint a bit. Go get a bench with your exemptions and you might be onto something there.
Raptors consider it because it's an instant rebuild without going through 3-4 years of pain to get it.