Looking at the moves Portland made at the deadline, this seems like a feasible strategy they're going for.

TORONTO: They get off OG's contract while he still has good value and they don't have to pay him a max extension. Sign and Trade FVV for pieces. A backcourt of Simons and GTJ is probably what the Blazers expected to have when they drafted them both, but Toronto would have some serious firepower from 3 with those two. It also gives Scottie more space to work within as Point Forward.

CHICAGO: Either Portland makes the playoffs and the Bulls get their FRP, or Portland trades the NYK FRP to get their own pick back and be able to trade firsts in the future.

PORTLAND: Simons and Dame do not fit together. The development of Shaedon Sharpe gives Dame a better fitting protegé to work with. The limited touches of sophomore Sharpe also means OG Anunoby can get more touches on offense like he wanted.