Ok - moved my post here;
Bridges is actually limited to a 4y 156 million extension. It's a bit like the Deni situation - he could sign for over $200 million on a 4 year deal this summer.
I wonder if its possible that is the Blazers cap space plan is to carve out max cap space for Bridges in 11 months? They would probably have to dump one of Jrue/Grant and possibly renounce Sharpe to make that all work. Bridges and Dame are very close. He goes from being the ~4th option in NY to 2nd option here.
To me, Bridges ain't it. They need a legit star.
Booker
Giannis
Embiid
Brown
That caliber. A legit second star who fits the immediate timeline because you have to figure they have MAYBE a two year window. This is the all-in, go for broke move that we were begging for. It hinges on Dame being Dame. You keep Tou and Deni and probably DC unless you trade for a center. To me this is the move where you push in all the chips, Shae/Scoot/Milwaukee picks/Orlando pick, etc.
Giannis I can see.
Brown I can see. I doubt he will be available in the next 2-3 years, but if he were yes I can see that.
Embiid knees are turning into a blend of Oden/Roy. I'm not sure he will ever get through an NBA season again. I'm not even sure I'd take on that contract for free. Maybe thats the type of move just to give Philly cap relief and hope Embiid can give you one healthy playoff run. Last season he played 19 games and the year prior 39. He's averaged 41 games per season over an 11 year career so its not like its now just two atypical seasons. Kind of relied on athleticism to be effective so even if healthy in two years I'm not sure a 33+ year old Embiid is that effective.
Booker isn't a great defender and duplicates all of Dame strengths. I don't see that duo contending at all. Its basically an upgraded DameCJ pair but with Dame being 36. Booker only playoff win with Durant was against an injured Clippers team once Kawhi went out. Durant has been way better the last 3 years than Dame will be. I'd pass on this deal too.
Of course keep an eye out for Jalen Williams, Chet, Mobley, Cade, Paolo, Bam, Edwards, Luka - etc. Maybe something happens with one of their situations and the team wants to cut salary or pivot to a rebuild in the next 18 months. I bet the odds are highly against that for any single one of these guys, but for the group of a dozen its possible one becomes available.
Unless its a Giannis/Brown type of deal or those other younger names I tend to think there might not be any worthwhile time to push "all-in". It needs to be a combo of many things happening at once. The players current situation not working, the Blazers offering in trade what the other team wants, as you say Dame regaining most his form, plus that star wanting to come to PDX.
It might be far more likely and preferred to go after a younger player and hope he will become the next star or at least a Siakam quality robin level of allstar. So basically trying to do another Deni type of trade. Or try to assemble a strong starting 5 like the Billups Pistons.