Do Nylander, Keefe Have Futures With The Leafs? You Can Bet On It

Among the unfinished business in Leaf Land as opening night of the NHL season approaches is the task of getting William Nylander inked to a contract extension in the wake of a career year. Last season, he tied Auston Matthews for the team lead with 40 goals and trailed only Mitch Marner with 82 points.

Offseason talks have produced no agreement between the club and Nylander, who is entering the final season of a six-year, $45 million contract, and no further updates are expected from Maple Leafs GM Brad Treliving until a new deal is done.

While Nylander prefers to negotiate away from the prying eyes of the Toronto sports media, he has still emerged as a +550 bet to be dealt by Toronto before the trade deadline. However, plenty of factors need to be considered before jumping on those lucrative NHL odds.

Lengthy Contract Negotiations Nothing New for Nylander

For starters, long drawn-out negotiations between Nylander and the Buds are nothing new. Nylander embarked on the longest holdout of the NHL’s salary cap era and risked missing the entire 2018-2019 season when he played hardball with the club five years ago.

But before calling out the shifty Swede as greedy, it is important to remember that Nylander never threatened to demand a trade or go public with his contract demands during that holdout. Indeed, the opposite was true, always a class act, Nylander seized every opportunity to reiterate his desire to remain a Leaf.

In fact, any blame for the Nylander’s 2018 holdout belongs to Kyle Dubas. The former Leafs GM furnished Matthews, Marner, and John Tavares with generous contracts while tossing scraps at the player who went on to be Toronto’s top playoff performer by racking up club highs of 12 goals and 25 points over the past three springs.

Treliving Arrives in Toronto with Checkered Track Record

Another thing working in Nylander’s favour is the calm that has overcome the team since Treliving took over the GM reins, bringing a welcome end to the circus act that marked the final days of the Dubas regime.

However, Treliving’s less than glowing track record in a quarter-century-long career in pro hockey management can’t help but make one nervous.

During a decade as assistant general manager and later general manager of the Arizona Coyotes, the team made the playoffs just three times, winning just two series. His subsequent nine-year tenure as Calgary Flames GM was marked with consistent playoff disappointment and questionable moves such as giving up multiple high picks for Travis Hamonic, and adding Adam Fox as a throw-in in the deal that sent Dougie Hamilton to Carolina, not to mention his inability to get stars like Matthew Tkachuk and Johnny Gaudreau signed to new deals.

That history has left some fans questioning Treliving’s move to retain head coach Sheldon Keefe, who has guided the club to back-to-back 50-win seasons but has failed to translate that into playoff success.

Keefe Enjoys No Loyalty from Treliving

With Keefe no longer enjoying the protection of his old buddy Dubas, he has opened as an attractive +400 bet on the NHL season specials to be fired at some point this season.

The Leafs have made steady progress while feasting on a steady diet of September dates with the Montreal Canadiens this preseason, and the decision to move Nylander back to his natural position as centre bodes well for both Nylander and a club that is likely quietly eager to rid itself of veteran centre and current captain Tavares and his bloated contract.

There is no doubt that Nylander deserves a big raise, but things could change quickly. Keefe’s ongoing employment will depend on avoiding any lengthy mid-season meltdowns, while another season filled with goaltending injuries could force Treliving’s hand at the deadline.

Ultimately, Treliving is unlikely to win any fans among Leafs Nation or in the Leafs dressing room by trading Nylander. His 10-team no-trade clause limits trade options at the deadline, and Nylander’s performance, both on and off the ice, makes him a legit candidate to wear the captain’s C when the Leafs finally dump Tavares.

As for Keefe, he offers value as a +400 bet to get the boot by a GM who didn’t hire him, should the Maple Leafs once again fail to fulfill the promise as +200 favourites to win the Atlantic Division crown.