Hear me out. Even though there's mostly second round picks, this sets up Toronto for a rebuild. And if I were the Blazers front office and wanted to keep the third pick from this year's draft, I would do this because there's potential that we could add Scoot Henderson to replace Simons for a cheaper contract, and we get an all star in Pascal Siakam. Obviously we'd need to pray for the Hornets to draft Brandon Miller (which is still possible), but yeah. Also Nurkic is here for more depth for Toronto. Also the reason why Sharpe isn't here is because I believe if the Blazers were to trade both Simons and Sharpe, it would have to be for a superstar like Embiid or Giannis. While Pascal is still good, he just isn't at that level of stardom. A potential lineup could be this if everything goes to plan:

PG: Damian Lillard SG: Scoot Henderson SF: Shaedon Sharpe PF: Jerami Grant C: Pascal Siakam

If you say Siakam can't play center your wrong because Toronto has done it dozens of times; and he has the wingspan and length to cover it. I can admit that Sharpe at SF is a little questionable, but this is just a scenario.