Well, with Dame gone he shouldn't be. Sharpe should be starting at the 3 (unless they trade Ant), and I want Rupert playing behind him to develop him. Rupert might be my favorite move of Cronin's entire tenure, I think he can be a lockdown defender with some offensive upside and the sooner the Blazers allow him to try and tap into that, the better. Also, the Blazers should have cap space next year and I'm interested in maximizing that, as it'd allow Portland to take a chance on better role players than Thybulle, or at the very least would give them the ability to take on salary for assets without sending anything back.
There's also a chance that the Dame trade generates a $20M-$30M TPE. I hope the Blazers have enough of a buffer below the tax to use that TPE to help other teams at next years trade deadline by taking on contracts in return for assets. That's what smart rebuilding teams do.
I don't think there's much of a chance the Blazers win in the next couple of seasons, so keeping Thybulle isn't all that important to me. If the Blazers feel like they can flip him for assets back, sure, but he barely fetched Philadelphia anything on half the price last season, so I don't see how Portland could get much more than a 2nd round pick or two. I don't think that's worth risking the flexibility and limited Ruperts minutes behind Sharpe. I'd rather find a cheap shooter for the 3rd guard spot (Skylar Mays?) to play limited minutes along with moving Sharpe down to the 2 to open up more minutes for Rupert at the 3.