Maybe it’s an unfair question, but let’s ask it anyway.

Can the Maple Leafs win a Stanley Cup if Phil Kessel is their best player?

Sorry, that’s my inner Tim Leiweke talking. Let’s get realistic and reframe the opening with a touch of Johnny Bower pragmatism. How about this: Can the Leafs win anything of significance — say, their first playoff series in a decade — with Kessel as their numero uno?

Seeing as Toronto’s NHL team signed Kessel to an eight-year contract extension worth $64 million on Tuesday — only the richest contract haul in franchise history — there aren’t many citizens of this city who don’t want to believe they can. It’s hard not to love this city when it’s in hysterics for its sporting heroes.

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But the truth is it’s a hard question to answer. It’s the same thing as asking: Can the Leafs win anything of significance if their pudgy designated goal scorer happily sports multiple chins in a league dominated by gluten-free, goji-berry-favouring fitness nuts? Can the Leafs win if their best player, the fastest skater on the team when there’s a goal in his sights, becomes a slow-as-anything laggard when coach Randy Carlyle asks for extra effort near the not-so-merciful conclusion of a long practice?

Nobody knows the answer to these questions. What we do know is this. Phil Kessel is a phenomenally gifted athlete who scores goals at a rate few NHL players can match. And if he’s been plagued by accusations that he’s a perimeter-hugging, conditioning-be-damned softie who’s been known to have great Octobers followed by significantly less impressive Novembers through Aprils — well, Kessel certainly turned around that perception during last spring’s playoff series against his former team, the Boston Bruins. Yes, it was just one series. And yes, it was a series in which Kessel will go down as the top man for one of the great choke machines in sports history. But Kessel scored four goals in those seven games — that’s a 46-goal regular-season pace, folks.

Some players sign for big dough in the wake of contract seasons. In Toronto, where Leafs management was won over to No. 81’s charms in the post-season, Kessel essentially cashed in on a contract series.

Canthe Leafs win the Stanley Cup if Phil Kessel is their best player? Have your say in the comments

Don’t get it wrong. There’s plenty to like about the deal. Kessel, who turns 26 on Wednesday, will be locked up for what will theoretically be his competitive prime. That he chose to stay in Hogtown instead of disappearing into the comfortable obscurity of a sunshine state, where he easily could have made comparable dollars if he’d exercised his right to free agency next summer, says something about his willingness to reside on the hot seat. Goal scorers, in a league in which goal scoring is at a depressingly low ebb, are precious commodities. Kessel is one of the best, even if he’s one-dimensional. With all that in mind, the game’s current financial landscape dictated that the Leafs were essentially handcuffed into paying Kessel, even if he doesn’t fit with Carlyle’s work-ethic-is-everything culture.

What hockey fans are about to find out, in their first experience with an NHL collective bargaining agreement that limits the maximum term of contracts à la the NBA, is that this sort of salary-cap environment creates strange peers. Every player who can make a wholly compelling case for a top-of-the-food-chain contract isn’t created equally. In the NBA, which pioneered this kind of structure, the best player in the league, LeBron James, makes a comparable buck to the top-paid player on the Toronto Raptors, Rudy Gay. James will earn $19.1 million to Gay’s $17.8 million this coming season. Anyone who’s seen a few games can tell you Gay isn’t half the player James is, and yet he’s pulling in 93 per cent of James’s salary.

And that’s the sad joke of a harsh salary-cap reality. When the marquee players are on the other teams, sometimes your squad has no choice but to pay up while pretending your team’s No. 1 guy is a reasonable facsimile of the actual alpha dogs, even when he really isn’t.

With that in mind, Leaf fans will be excused for being at least somewhat alarmed at the rare company in which Kessel suddenly finds himself.

The list of men who’ll earn a cap hit in the neighbourhood of Kessel’s $8 million come 2014-15 includes Corey Perry, a former Hart Trophy winner who scored 50 goals a couple of years back. It includes Steven Stamkos, who has scored 60 goals in a season. It includes Claude Giroux, a centre who averaged a smidgeon less than point a game on a run to the Stanley Cup final a couple of years back. It also includes Sidney Crosby.

Crosby has devoted his life to becoming the ultimate hockey player. Kessel, a scorer of 37 goals in his best season, is known by teammates to be a devoted ping-pong enthusiast and card player.

As Daniel Negreanu, the Canadian Texas Hold ’Em whiz, tweeted in Kessel’s direction on Tuesday: “Congratulations .... Now we can play MUCH higher limits at the poker table!”

Nobody’s begrudging anybody their fun. If the NHL’s salary cap skyrockets like some projections suggest it will in the coming years, Kessel won’t be among the league’s highest-paid players for long, just as he won’t have to be Toronto’s best player forever. Most elite teams give their big dollars up the middle. Kessel is no more a centreman than he is a centrepiece. The best-case scenario is that Kessel turns into Toronto’s version of Patrick Kane, Chicago’s gifted if goofy winger, this assuming the Leafs can find their equivalent of Jonathan Toews.

As an optimist, you’d like to think Kessel is capable of improving and evolving and dominating. As a realist, you know Kessel has only ever been described as being “driven” on the days he catches a lift to the rink with his roommate Bozie.

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You know that the way this club is currently concocted, there’s far too much pressure on Kessel to carry the load. You know that the way it will ideally be constructed, he’ll be a skilled sideman. That’s not to say it’ll be easy from here on out — except, maybe, for Kessel. Said the man of the hour on Tuesday, describing his feelings upon signing his extension: “It’s a day you don’t have to worry about anything anymore.”

It’s safe to say Kessel, at that moment, was the only citizen of Leafland to whom the same thought occurred.

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