I do not want OG Anunoby as the focal point of a Dame trade. Dude either walks for nothing or we end up overpaying him and could be paying a starless forward duo a combined $70M a year.
If we plan on flipping him, it would need to be now, as I don't see him having more value mid-season with free agency coming up. He also wants more offensive responsibility and spending a season trying to please him in order to convince him to re-sign might get in the way of focusing on the development of Scoot, Sharpe, and Simons which is the most important thing this year.
I'd rather have Miami picks, have a better chance at having a top pick next year (because we're worse) and adding a future star to the Portland core on a rookie salary. Trade Jerami for whatever assets we can get. That'd open up cap space in the future which could be used to accumulate assets like rebuilding teams do. And then hopefully Miami can't recover from having no young core or picks to replace Lillard and Butler once they retire or decline. Having control of Miami picks from 2027-2030 (two 1sts & two swaps) could result in a top 5 pick (or multiple) to trade for starpower or draft starpower (as Scoot and Sharpe will still be 26 & 27 in 2030).
In the future, we'll be wanting to add the star forward to Scoot & Sharpe that we always wanted to get for Dame. Putting ourselves in the best position to have assets and numerous chances at doing so seems best. Punting on that route to get a high-quality role player right now that could walk or will likely get overpaid doesn't seem smart.
Chose a consistent direction and stick to it - rebuild.