Well if there's no agreement he can't play, he isn't arbitration eligible so he's holding out until ink is on a contract. He won't be a UFA until 2028 too. Theoretically they could agree on a small bridge contract to take him to arbitration, but it doesn't feel like either side would want that (in my opinion).
Unless Raymond comes out and says he does not want to play for the Red Wings because of the contract negotiations I can't imagine they trade him. If we get into training camp I'll start worrying about our RFAs not being signed personally, but right now I expect them to get deals done because it just is the most likely scenario all things considered. Yzerman has had late signings like this in Tampa and Detroit so it isn't too shocking even though I'd rather they be done already!