Two first pick of 2018 are so valuable that any team might want them.

Detroit is probably the team that can offer the most,
Green 50% retained+ 2 rooster player depending on nyi cap situation.

If phili decides to do a quick rebuild based on their young prospect they could offer simmons wich is probably on one of the top5 friendly deal in the league. Pairing him with tavares could be brutal, also they could send another player on a cheaper contract and taking kulemin as a cap dump to allow nyi to have more room

With only a nik over 3 mil in space its hard to move a lot of talent but with some cap dump trade you could gate almost anyone

I agree the Isles need to send back cap in most trades. Kulemin would likely be the go-to cap dump asset there. However, I have to wonder if PHI would take Clutterbuck. With his playstyle, PHI fans would adore him. And I like you idea of Simmonds, I get a feeling he'd fit in on the island.

Would PHI be willing to retain salary on Giroux? If so, maybe 3 1sts and Clutterbuck for 2m retained Giroux?

The value for phili is certenly there but the probleme with retainning salary is the term of giroux contract, by the time it ends all their young player eill be on new an expencive contract i wouldnt see a probleme with 1.25 mil maybe 2m is okay if phili then trade other pricy player in the same rebuild optic.
Would certainly be intresting a 1-2 punch of giroux-tavares would give crosby-malkin a run for their money.