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Life is a learning experience and the adage “once bitten, twice shy” or as the great philosopher Montgomery Scott once said, “fool me once…shame on you, fool me twice…shame on me”. That is something that Toronto Maple Leafs GM Brad Treliving has to be prepared for in his new gig, with core players in a precarious situation just like they were in Calgary the last two years.
The Flames were one of the best clubs in the NHL two years ago, mainly because of a superstar top line of Johnny Gaudreau, Matthew Tkachuk, and Elias Lindholm. Treliving tried to get pending UFA Gaudreau locked up, but a modified no-trade clause kicked in before the final year of his deal and after scoring 115 points in his walk year, the New Jersey native was set up perfectly to hit it big in free agency.
In spite of Calgary offering more money than other suitors, Gaudreau ended up signing in Columbus.
The agent for Gaudreau was Lewis Gross, the same as Leafs winger William Nylander. All indications since Treliving joined Toronto last month is that all things being equal, the Leafs would like to keep the core four together, but that might only be necessitated if their ask on a new contract would have a slight hometown discount. That is not expected with Auston Matthews over the next few weeks and when an extension talk comes up next summer for Mitch Marner, so it is logical that would be the case for Nylander, who scored a career-high 40 goals last season.
Unlike Gaudreau, who had a no-trade that limited his destination to five teams in the last year, Nylander has a 10-team no-trade list that goes into effect July 1. Even going into the summer, the Leafs would have the avenue of trading the winger to almost two-thirds of the NHL. That being the case, Treliving can afford to be patient and wait for Gross to put forth a contract proposal if Nylander wants to stay in Toronto.
If the winger’s camp tries to play hard to get and refuses to be tied down to an offer going into the final year of his deal or is looking for a big number (speculation is that Filip Forsberg’s eight-year, $68 million deal would be the starting point), then Treliving cannot risk Nylander walking for nothing and has to see what is out there in the trade market in the next month or so.
Toronto Maple Leafs Blogger • 
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