Joined: Jul 2018
I think there needs to be a N/A option.
The Jets have to accept the deal, so you can't blame them. We have no idea if there was an opportunity to sign him long term, so it's hard to judge based on anything like that.
The Jets will get one more year of Trouba, and he will be motivated if he wants a big contract, and by creating interest, there is a better chance a team he wants to play for long term will be in the running if the Jets try to trade him next offseason. The biggest risk for the Jets would be if he doesn't want to sign an extension with that new team immediately, his value would be no different than if he were one year away from UFA status, as he can just elect for arbitration and likely just get a 1 year deal again which would bring him right to UFA status.
I think both sides are handling this as well as can be expected. There are no nasty rumors coming out, and neither side is disparaging the other. Trouba has played very well, said nothing but good things about his team, and hasn't sat out any actual games. He has no obligation to commit more than 7 years to the organization that drafted him and he will play his 6th for them this year. This leaves Winnipeg a scenario where they can get 6 years service out of him, and still receive some compensation for him from another team. It is what it is.
Personally I think Winnipeg should just go for it this year, and if he is still unwilling to re-sign, move him at next year's draft. I don't think there is a player Winnipeg could trade for that fills a bigger need than trading away Trouba would create.