Should the Leafs trade Phil Kessel?

Settle down. Before you lose your cool and start using your naughty words in the comments, take a moment and consider the following:

Phil Kessel has one year left on his contract before qualifying for unrestricted free agency in July 2014. Point production (and goal scoring) tends to peak around age 25. Assuming that he makes at least the same salary, if not higher, on his next contract, Kessel will likely under perform compared to his current deal. One would expect Kessel to have high value on the trade market and could net a package of prospects and picks.

I guess what this argument really comes down to is when the team's window is. Personally it seems like the Leafs have the offensive talent up front to compete this season. What the team really lacks is a top four defenseman to play behind Phaneuf and solid goaltending. They certainly score enough goals to win. If they can find a way to cut back on the goals against, this team is competitive. They won't be the favorites, but once you get into the playoffs, it's all about who gets hot. That's why it makes a lot of sense for the Leafs to swing a deal for Luongo. He's an elite talent available for under market value and would solve a critical issue that has plagued the team since Eddie Belfour. Think of the Blue Jays this winter: they called the Miami Marlins about pitcher Josh Johnson and wound up trading for five players. Sometimes things happen that can put pieces in place to make a run. If you get Luongo, maybe that means you push hard for a true #1C in the summer. And obviously you keep Kessel around because you're going for it.

The flip side is what if the Leafs stumble again and miss the playoffs? You've got several key pieces up for new deals over the next 12 months (Lupul, Kessel, Phaneuf, Gunnarsson, Kulemin even). Every season you aren't making a run, you're watching your best players age and possibly decline. On top of that, the prospect group behind these guys just isn't that deep. The only forward prospect with even a decent chance of being an NHL top-six player is Kadri, and even that's a question mark for me. So it seems unlikely at this point that Toronto can just add pieces from the farm system as other players decline (defense is a different story). The Leafs don't have much in the way of salary committed in the future. It gives them a lot of flexibility in deciding which direction they want to go. If they decide that it's time to start over again (ugh), it might be best to move some of those expiring deals and create a new window for the team a few years down the road. Calgary has been reluctant to do this for years now and they're treading water.

So....if the Leafs fail once again to make the dance, should they tear the roster down? Trade Kessel, Phaneuf, Grabovski, etc? Or should they stay the course and hope Kessel is still an elite goal scorer in a few years when the next window opens?

Should the Leafs look to trade Phil Kessel or other core pieces if they don't make the playoffs?