Can the Leafs afford a lame-duck Kessel this coming season?

When I wrote about Cody Franson’s contract status the other day—and if and where he would fit with the Maple Leafs going forward—I realized as I was developing that piece that I was not addressing the real elephant in the room: do the Leafs need to sign winger Phil Kessel to a long-term contract before a new season gets underway? (On the Franson matter, we'll see if Fraser's new deal will make it easier for Nonis to re-sign Franson...) 

Both sides are saying little, of course.  It’s not Kessel’s “style” to make public waves out of the blue and Nonis is hardly about to start talking about any negotiations that are—or aren’t—happening in public.  But there are two things that I keep batting around in my own head, and I really believe they are relevant to any discussion about the kind of team the Leafs will be in the years ahead:  is Kessel the kind of player that you want to pay superstar/cornerstone player money to and if so, does that type of deal not have to happen now, before he smells free agency and his agent nudges him to seek the largest and longest-term deal he can? (Keep in mind this will be Kessel’s one and only opportunity to hit pay-dirt in free-agency when he is still 20-something.  He will sign for at least six seasons and by then, players with his attributes, in my view, tend to decline. This is his ultimate earning window.)

I know some people (and teams) are of the view that these things can always get worked out later, as in why not put off until tomorrow what doesn’t really have to get done today.  But the problem I see with that is very simple:  I’m sure the Predators thought Gary Suter was happy in a low-stress environment and that they could convince him to stay a Predator for life.  That didn’t exactly happen.

It was the same with Parise and the Devils.  I believe Lou Lamoriello honestly thought he would be able to get the gritty winger to re-sign for at least a bit of a hometown discount, given his relationship with the organization and his growing popularity with the fans in Jersey.

Again, we know how that story ended up.

Both of those guys were hard-working, high-end, loyal individuals.  Yet they did not sign with their respective teams before free-agency was upon them, and then bolted the moment they had the chance—though they were both offered huge money to stay.

I’m sure we have all noticed the trend in recent years, NHL teams trying to lock-up their best and most productive players before they hit their free-agent season.  There is no doubt they sometimes over-pay, but as Anaheim did with Getzlaf and Perry, they want to make sure they don’t lose the core of their team for nothing if those players were to walk in free-agency.

I know that Leaf fans (some, at least) will feel that with Bozak signing his new deal, his friend Kessel will naturally want to stay here and play with his buddy for the rest of their NHL lives. That said, I see little evidence over the years of “friendship” leading to players staying with their current clubs.

But before we get to the second of my questions, let’s  talk about the first:  is Phil Kessel the kind of player, in your opinion, that the Maple Leafs should be investing “best player”/cornerstone money to?  We all know that, in this day and age of monopoly money, that means a minimum of 8 million dollars a season for what, seven or eight seasons?

Now, that type of money usually goes to guys who are not just highly-skilled but also leader types, individuals who are multi-dimensional players.  (Not always, I realize—Kovalchuk, for example, was never thought to be a true leader and certainly not a complete player until more recently…)  I want to be careful how I frame this, but Kessel, while still young and maturing, has never presented as anything close to a leader with the Leafs. His teammates may beg to differ, but I just don’t see it.  A dynamic player, sure.  Explosive and  dangerous, yes.  Maybe even a game-changer in the current-era tight-checking NHL, because he can score out of nowhere and turn the tide in a game suddenly.  That has value, absolutely.

We know he will likely never be Bryan Trottier, Bob Gainey or a latter-day Steve Yzerman as a defensive forward (or Pavel Datsyuk, for that matter) but we also have seen a gradual (if at times almost imperceptible) development in his two-way game under Carlyle.

He’s in or just entering his prime.  So is he the kind of performer that deserves (or even if he doesn’t deserve it, are the Leafs in a place where they need to lock him up because he’s the best they’ve got?) cornerstone player money for almost the next decade?

And depending on how you feel about that may directly impact how you respond to our second question today:  do the Leafs need to act now, this summer, to extend Kessel to ensure we don’t go into a lame-duck season?

We all know what often happens in these cases.  If no deal is reached, training camp begins and if nothing happens by the beginning of the regular-season, both parties will agree to put off negotiations until after the season so it won’t be a “distraction” for the player or the team. 

And we know, in today’s NHL, how that movie usually ends.

Maybe you don’t particularly care if Kessel stays.  Perhaps you’re in the (small?) contingent of Leaf supporters who actually feel we should “sell high” and get a boat-load of younger players and prospects for Kessel or maybe even that stud defenseman I/we keep talking about here.

Whether or not they see him as a superstar the Leafs can build a championmship team around (we're back to that leadership thing again), my sense is most Leaf fans would in fact like to keep Kessel as a central piece for the future.  Still, for that to happen, I have this feeling that Nonis needs to make something happen—and soon.

Your thoughts?