Portland needs to go all-in with their rebuild and should move off their more experienced players for youth.
Trade One. Anfernee Simons & Matisse Thybulle To Orlando for Orlando using their 2024 first-round pick for Portland and Orlando's 2025 first-round pick, Anthony Black and/or Wendell Carter Jr.
There's a bit of a log jam for impact playing time at guard. As of now, it looks like Scoot Henderson & Shadon Sharpe are the long-term PG & SG. With Anfernee Simons and Malcolm Brogdon taking time from each other as 6th-man guards. Brogdon could be moved over Simons, but I think Brogdon is more suited for this role and I also think Portland gets more in return While The Blazers could use some improvement in regards to their starting forwards. I think there is a log jam in their rotational players. I think a rebuilding team should get younger even in the rotation and hope that someone is a Dimond In The Rough. TBH I'm not as high on Anthony Black as I think a lot of people are. He was the 6th overall pick in last year's draft he is still under his rookie contract. I think the risk is worth it. I think Deandre Ayton is a good starting center and Portland doesn't need to be searching for his replacement, but he's not good enough for Portland not to be looking. I think Wendell Carter Jr. can push Ayton for playing time.
Orlando does this because they might be a dynamic scoring guard to complement Paolo Banchero & Franz Wagner from being a championship contender. Thybulle is probably a better fit for a win-now team.

Trade Two Jerami Grant, The 14th overall pick To Atlanta for Onyeka Okongwu, Saddiq Bey, and future picks. I think this trade is a real long shot. I think the Hawks may be making some major changes. I don't know if Grant will stay with Atlanta through the season. I don't want to give up the 14th pick, but because of his age 30 Grant might be seen as a risk. I believe Portland's biggest need is an old-school 90's power forward who can grab rebounds. The problem is that that kind of player doesn’t really exist anymore. I think their best bet is to convert a natural small center like Okongwu 6-8, 235 or Robert Williams 6-9, 237 into that role. Depending on who Portland picks at seven Bey could find himself as the starting SF.

Possible starting lineup Henderson/Sharpe/Bey or 7th overall pick/Okongwu/Ayton.