If this team has any dreams of ever contending again, I think they need to not spend significant money on support pieces and need to allocate as much money as possible into 1 or 2 players while still keeping the depth sufficient. This can be interpreted as "don't pay depth guys", but this can also be extended into "don't pay Rakell and Smith $10 million combined, pay 1 guy $8 million and the other guy $2 million". If they have any ideas of contending again, that's what they need to do. This is also part of the reason why the Graves deal is looking like a mistake. You don't need to be paying Graves $4.5 million a year in a world where his RD partner is going to be Letang or Karlsson.
Instead of trying to get something like Smith-Malkin-Rust as a line for Malkin, go for something like Bemstrom-Malkin-Reinhart. Get one major addition and play a lesser linemate that you hope can outperform his contract in the role. I'd be completely fine if they did that with Crosby's line as well, but I personally really like the Crosby-Rust duo at this point.
If this team ever wins again, it won't be because they're paying good players fair value. It's because they'll be paying good players for much cheaper than the value they provide, which allows them to pay great players fair value. Paying good players (let's take out the Graves debate here) fair value won't help this team do anything. Getting someone like O'Connor to be a sufficient 3rd wheel on Malkin's line, which allows them to add a big name piece like Reinhart as the other wing, is going to be how this team could win something again. Or having POJ play 19 minutes a night while being sheltered by Karlsson, which gives them more money to spend at forward, is going to be how this team could win something again.
But in the end, it's a moot point because this team isn't going to make the aggressive decisions needed to actually pull this off. They're better off just ripping off the bandaid and just starting the rebuild now.