With the rise of Shaedon Sharpe, I would rather have him at the 2. Lillard would then be flanked from Position 2 to 5 with defenders, who also isnt bad at offense. I love Simons, but understand that he is being under utilized when Dame is on the floor with him. If Portland actually wants to get better defensively, they cant have 2 minus defenders on the floor at the same time. That's why Blazers defense was just awful last year, they kept exploiting Ant and Dame. Brown is what you hope a Brandon Miller can become, an All NBA talent. The benefit for Portland is Brown matches Lillard's timeline.

If you are Brad Stevens, Beal and a first round pick is a good exit strategy for a player that just cant go Left. Boston will be stuck paying Brown and locking their team up for the foreseeable future. with the 23rd pick, Boston can draft someone that would be ready to contribute now like Kris Murray that can do 80% of what you need Brown to do on a rookie scale contract. Beal would be perfect next to Tatum.

For the wizards, This is everything you are waiting for, you just get to reload. You get a very dynamic guard that is a younger and taller clone of Dame Lillard, on a really cheap contract; and you also get to build around with either Scoot or Brandon Miller. Which is also co-incidentally a great pairing with Simons. You can still trade away other assets like Kuzma and Porzingis for other draft capital and your rebuild will go very fast.