Outcome 3 is where the major disparity is. What is a reasonable price, and to whom? Obviously opposing teams want Trouba and will only pay what's necessary to get him, but if you turn around and set the bar low then instead of the Jets getting anything of worth you get nothing of need and lose a very valuable piece of your hockey club. How does that benefit us? Winnipeg is known for having hockey loving fans, but this city is not appealing to most players. Letting Trouba be the example that Winnipeg won't be bullied by agents for young talented players is a fair price to pay to hopefully deter such actions in the future. Otherwise, what's to stop Ehlers, Morrissey, Connor, and Laine from holding out if they don't like the direction their career may be headed? For a small market team, we can't allow ourselves to be bullied by agents. It wouldn't stop there, other GM's would bend us over like Benning every time we find ourselves in a situation.
Simply put, trading him at a diminished value to get rid of him so he's happy does not help our team now, or in the future. The return will be mediocre, and it won't change the perception of playing in Winnipeg for the better regardless so you might as well get as much as you can when trading him or let him sit. It's about what's best for our team, not the Trouba brand, the Trouba player, or his girlfriend. If it works out for him too, then everyone's happy. Otherwise, he's the one being unreasonable (Overhardt refusing to look at deals) and he can deal with the consequences of holding out.