I'm not sure how to make the value fit such that both teams would accept, but I think the basic framework of OG for Simons makes a lot of sense.

For Toronto, they've got a wealth of big frontcourt players, but are short on backcourt talent. FVV was at his best playing next to Lowry, and isn't likely suited as a lead guard. Simons was excellent when Dame was out last year, and has shown the potential to be a really good lead guard. His high volume three point shooting should also open up space for Siakam, Scottie and Poeltl to operate (especially in conjunction with the Gradey Dick addition).

For the Blazers, something's gotta give. They have Dame, Scoot, Sharpe and Simons all in their backcourt, with Jerami Grant as their only starting caliber wing. Simons is the odd guy out, and OG is exactly what they need. There aren't actually a ton of landing spots for Simons whose archetype of player isn't nearly as highly valued as OG, and the Blazers are in a bit of a tough spot as they have pressure to make a move to clear up the backcourt glut. I think adding Kris Murray and a future first probably gets the deal done.

Adding Boucher is a nice boost for the Blazers, who have serious depth issues, and the Raps would likely be pretty ok with including him in here because it will make it easier to re-sign both FVV and Poeltl while staying under the luxury tax.

Overall, who says no?