So here's an idea that's almost certainly a little whiskey-aided. Right now the Leafs should be looking to trade Kessel. To get a good return for Kessel I think you need to find a team that:
A) Is on the cusp of being quite good, as a bad team won't want to build around him and a good team probably won't have the cap space
B) Won't be scared off too much by the "character concerns"
C) Will play an up-tempo sort of game that makes the most out of Kessel's speed and shot
D) Has enough good young players in place that they won't be selling the farm in order for the Leafs to get a good return
So Edmonton gets mentioned as a potential trade destination but I really think they're too bad to make those kinds of moves. I think you need to think your core is in place to take that next step. So what about Calgary? They're a team that will probably just miss the playoffs with a top young centre already in place, a team that could use some secondary scoring and has a guy running the team who's pretty big on Kessel. So what about something like this:
To Calgary:
Phil Kessel, Jake Gardiner, James Reimer
To Toronto:
Sam Bennett, Matt Stajan, Ladislav Smid, 2015 second round pick
Now, ordinarily Bennett is the sort of prospect I would rule out getting traded at all but I think this makes some sense. Monahan is already there and forming a pretty solid combination with Gaudreau. They add three players Burke likes who each fill a need of sorts. The Leafs eat some bad money but get a top centre prospect and a top 45 draft pick. Matt Stajan returns to Toronto, which I think is would be hilarious.
But more to the point this deal would pass my central smell test which is I don't think it's a clear win for both sides and, as a Leafs fan, I'd have to think about it. I'd love to land Bennett but while I don't think Kessel individually could land a prospect with his sort of upside I do legitimately think there's a possibility that dealing Kessel, Gardiner and Reimer individually could land a collection of picks/prospects that might work out better.
Calgary takes on a lot of risk and Burke runs the risk of the bad optics of trading another top young centre for Kessel. That said, with Ramo leaving they add a potential top 10 scorer in the league, a good mobile defenseman and a serviceable back-up goalie while only increasing their cap commitments by 8 million or so and it might be argued that they're a team that will have a hard time landing premium UFA's.
I've probably overthought it. A Kessel to Calgary trade would probaby just revolve around the 13th or 14th pick or whatever they end up with. Still, I could talk myself into it if I were running either team.
