Desperate contracts hinder Leafs’ future

Photo: Frank Gunn/CP

The Toronto Maple Leafs’ creaking, oil-leaking wreck finally rolled to a stop with their elimination from playoff contention in Tampa Bay Tuesday night. But there was no greater foreshadowing of the Leafs’ failure in approach than their appearance on HBO’s 24/7.

For a fake documentary it was pretty revealing, and not just because we learned Leafs head coach Randy Carlyle can’t work a toaster. More telling—and troubling—was the highly stage-managed signing of the seven-year, $49-million contract extension the franchise gave to Dion Phaneuf.

Rumoured for weeks, the actual deed was done on New Year’s Eve as the Leafs and Leafs Nation gathered in Ann Arbour, Mich., for the Winter Classic on New Year’s Day, and it was captured on camera for all to see. It made for a wonderful plot line, but, like so many other things done for dramatic effect, it didn’t hold up once the lights went down.

Today it’s hard not to look back at the whole thing and cringe. The deal promises to be yet another albatross as the Leafs try to figure out how to be a better hockey team—it also perfectly represents why they’re not.

Maybe it’s the 47 years without a championship or  the challenge of finding true north in a market so clouded with competing electrical fields. But somehow the Leafs seem to have a self-esteem problem, or else why would they keep giving big money and long-term deals to players not up to the tasks assigned them with no apparent appreciation of leverage?

Consider the deals that have littered the Leafs lineup in the past two years alone—a period that precedes Dave Nonis’s inheritance of the GM job but includes him being the negotiator-in-chief on behalf of the since-departed Brian Burke.

The Leafs have a core of players all right, but for the most part they are a core by default: a group of unaccomplished guys with deals that are both rich in average annual value and uncomfortably long.

Remember when Mikhail Grabovski got the five-year, $27.5-million contract that Nonis had to spend $14 million to buy him out of last summer? He got that on March 6, 2012, after scoring not a single goal in 14 games in February, a swoon that corresponded almost identically with the three-points-in-11 games crash that cost the Leafs a playoff spot and Ron Wilson his job that season.

That deal came a couple of months after the Leafs gave tiny defenceman John-Michael Liles a top-dollar, four-year, $15.5-million deal while the then 31-year-old was out for five weeks with a concussion.

In both cases the contracts came when the players should have been on their back foot in negotiations, and yet in each case they emerged with player-friendly deals the club very quickly came to regret.

They didn’t learn from them, however.

The knock against Joffrey Lupul when he arrived in Toronto—fair or not—was that he had a hard time staying healthy. He was quick to demonstrate that he loved the big-city life and recognized the benefits of being a star in Toronto, but the club failed to test how badly he wanted to play here and was too quick to trust that his brittleness was behind him.

He played just 66 of 82 games in his first season in Toronto, in 2011–12, but that was enough to convince Nonis that he should get a five-year, $26.25-million contract after the first game of the lockout-shortened season a year ago. He played just 16 out of 48 games last season and managed 69 out of 82 this year.

Will that improve? A history of back problems, concussions, bad luck and being 31 years old next season suggest it probably won’t, but the Leafs have him under contract for four more years anyway.

Which brings us to David Clarkson and the seven-year, $36.75-million deal he signed in free agency last summer. The Leafs believe they got him at a discount; the Edmonton Oilers, for example, were willing to pay more.

Think about that for a moment.

Toronto is where Clarkson wanted to play—not Edmonton—but did Nonis ever properly value that? It’s hard to imagine he did, given that the deal was absolutely at the high end of the range a player like Clarkson could have conceivably gotten. The contract is also considered buyout-proof because according to Capgeek.com most of his remaining money ($24.25 million) is payable in the form of bonuses, and contains limited no-trade and a no-movement clause.

It is hard to criticize Nonis for the eight-year, $64-million contract extension he signed with Phil Kessel early this season, other than the timing. I guess Kessel could have earned a richer deal had the Leafs actually made the playoffs, but there is plenty of precedent in the NHL of star players taking cap-friendly deals to stay with winning teams, not that the Leafs are ever in position to apply it.

And now that the Leafs have faded out and Kessel managed just three goals since March 1 would Nonis not be in a better negotiating position now than he was coming off the fool’s gold of the 2013 playoff run?

Similarly, wouldn’t fixing the Leafs this off-season be easier if Phaneuf wasn’t under contract?

What was the rush, anyway?

If 24/7 revealed anything about him it’s that his Bentley-driving ego is perfectly in line with the starring role he’s written for himself as the captain who gets the girl and rescues Toronto from its Stanley Cup misery. It’s a star turn that should be considered a privilege; instead the Leafs rushed in to overpay Phaneuf in the vain hope he was the man for the job.

It appears he’s not, but signing him when they did made for great TV.

Unfortunately, like so many deals given to the Leafs’ under-performing core, it made them look desperate, which rarely makes for good business.