Weirdly enough? Toronto.
But actually I associate him more with Toronto mismanagement if that makes sense. Like, they thought they'd be good so they traded two firsts and a second for him, but they ended up being terrible so those picks ended up being high picks in Seguin and Dougie Hamilton. One playoff series in however many years (that game 7 loss) then they eventually trade him again because apparently it was time for a rebuild.
And I just looked this up, the draft the season after the Leafs traded Kessel away was when they drafted Auston Matthews. So I guess the front office redeemed themselves eventually.
Either way my answer is Toronto. And team Hot Dog which imo should definitely be a poll option