Winnipeg looks like the clear winner here; they are getting by far the best player in the whole scenario. I think they take this in a heart-beat, even with the loss of Trouba and Copp. Florida gets a lot of good peices but is losing their franchise 1C in Barkov. Nylander is great, but he isn’t at a Barkov level. I don’t think the Panthers take this deal. Toronto gets a true top pairing (or at least very good 2nd pairing) RHD, and that is worth Nylander (painful as shiping him out would be) and a very late 1st (at least mid-late 20s). Ekblad’s health is a concern (and his cap hit is hefty), but I think Toronto is willing to take the risk, since this trade immediately shores up their weakest position.
I would think if this scenario comes up, Toronto says yes, Winnipeg screams yes and Florida takes a long look and then walks away.
There is also the “trading within the division” issue here. Florida in particular wouldn’t be thrilled to see Toronto’s biggest (and frankly only) area of weakness suddenly shored up.