To be honest, I'm sure that's the sort of deal the Leafs are hoping to make but I just don't think the Jets do that. But I also think the Leafs would rather it be a 2017 1st round pick than a 2019 one.

Dude? You're at least looking at Kapanen+Gardiner+Toronto's 2nd round pick to get Jacob Trouba out of Winnipeg. Your proposal doesn't cut muster here.

If Carrick is honestly the best D man you offer for Trouba, Then i'm pretty sure that Cheveldayoff would look elsewhere when dealing Trouba.

Not sure another Top 4 D is what Winnipeg is after. I mean the whole reason Trouba wanted out is because he wanted top 3 minutes. With Myers back next season Trouba will probably be disgruntled again. Throw another pick and Bracco or Tymashov at them.
I used the 2019 1st because I hope that it will be 23rd or later by then and also because hopefully they will get Hague or Foote with the 2017

By all accounts Winnipeg needs Goaltending and Defense i believe their pretty barren when it comes to D in their farm system they've among the best forward corp around i think they need D and Goaltending help so you probably need to work from there.