Maybe my problem is that I’m mainly looking at it from the Sharks. I wouldn’t give up Braun for either of those guys. Also Braun is a 3 at worst. Only guy that I’d move Braun for in this thread is Simmonds. Maybe something like Braun+Karlsson for Simmonds+bottom pairing D (without a huge contract)
See, that's where the issue comes in. Take the Flyers' situation into account. Our core, moving forward, will be Provorov/Gostisbehere/Sanheim/Myers/Hart/Couturier/Konecny/Patrick/Frost/Farabee and whoever else slots in (Lindblom, Aube-Kubel, Vorobyov, Rubtsov, whoever.) G, Jake, JVR, and Simmer are older, and will be complimentary parts by the time we're truly ready to compete.
Couts is 26. Ghost is 25. The next oldest core pieces are 22 right now. Trading away someone young, who we expect to grow with the team and fill a critical role for years, is counterproductive. Meanwhile, the Sharks are looking for someone who's good now, because your window is now. Simmonds would have a lot more value to you, as you rightly pointed out, but to us, the value proposition is inverted, because Simmer's 30. He's the 7th oldest guy on our roster; as much as he's a great guy and still has a lot to give, he's not going to be there when we're really competing.... and therein lies the rub, because neither will Braun, who's also 30. For the Flyers, it's much easier to part with Simmonds than with Frost or Myers; they have more value to us, since their value comes into play when we most need it to.
What I'd really like to do is make the deal bigger by moving to better secondary parts: Braun+Donskoi for Simmonds+Gudas, who is more than a bottom-pairing guy, and the only expendable defenseman who has a reasonable contract. Donskoi will be around long enough to provide us additional value, and Braun fills a slot for a while; Simmer's a big add for you, and Gudas could conceivably step into your second pairing if you need him to; he's overqualified to be on the third pair (unless he's playing scared.) If the contract is an issue, the Flyers could retain on Simmonds; that does no harm to us, and it brings him down to about what Donskoi's paid. Gudas, meanwhile, represents a savings over Braun's deal.