Here's the one slight nuance where we disagree, though:
I don't think they're playing with fire; I think they're simply waiting as long as possible to keep their options open, on the off chance a trade does occur in time to clear more cap room for a multi-year deal. Then, if (once) it doesn't, they'll eventually sign for at or near their QOs just before camp opens. I could be wrong, but I'm 95% sure this isn't a big deal at all.
Heck, I wouldn't be surprised if Gorton and the two agents weren't already in complete agreement already on both 1-year (the QO) and 2-year deals – and just waiting to see if there's any chance at all that they'll be able to go the 2-year route.
Exactly, and if nothing else, we at least cannot look at their current unsigned status and conclude that an hold-out already have begun.
Maybe its because I am looking at these things more from an agent POV this is a given for me -- but like just imagine if you where the agent for one of these kids. If your client was OK with taking the contract offered to these kids -- would you advice them to sign it now or a couple of days before camp? Its easy to sit here and say lol, Gorton have been trying to make a trade for 4 months what would change now? Facts are that if you have your client sign now and then Gorton out of the blue manage to deal Namestnikov or someone tomorrow, the other kid (TDA or Lemiuex) would get a lot more money and you will have wasted a lot of money for your client. Or you wait and there is zero harm in that. For an adviser like a player agent is this decision is a total no-brainer.
Why? In the individual case the risk is low and looked at isolated probably neglect-able. But if you take these kind of decisions daily in your profession, those unnecessary risks that can be avoided at zero cost will materialize regularly enough and end up costing you in the end. Also you never have the full picture in these situations. What can seem like a very low risk situation can be a lot more risky than it seems.
In addition, the alternatives to these kind of risks can often feel a bit uncomfortable for the client (the player in this case), not saying that it does in this case, but in general. Won't I look bad if I wait? Should we really bring this text into the agreement, it will look like I don't trust the other side. And so forth. The adviser will however go to lengths to avoid them for the above reasons.