Time could make sorting out Maple Leafs contracts even tougher

NHL insider Luke Fox joins Shawn McKenzie at Maple Leafs skate to discuss whether we should be concerned about William Nylander not yet having a contract, and why Justin Holl is a name to watch out for at camp.

TORONTO – A week out from training camp and still no more clarity on how the Toronto Maple Leafs will keep the band together for years to come.

Kyle Dubas shouldn’t be doubted when he says that there’s enough cap space to sign Auston Matthews, Mitch Marner and William Nylander to their second NHL contracts, but what remains to be seen is how much is left for everyone else once those deals are eventually done.

The newly minted Leafs general manager has spent the summer reminding agents about the importance of the greater good. To wit: If each player takes a little less than absolute market value, the Leafs will have a better chance of keeping their core intact and chasing championships for a sporting generation.

It’s the next phase of a long-held plan inside the organization’s executive boardroom. Team president Brendan Shanahan cited it as one of the reasons his Detroit Red Wings were able to sustain a strong run of success in the late 1990s and early 2000s during an appearance on "Prime Time Sports" last September. The Hall of Fame winger said he was comfortable taking a little less in his playing days “because I was in a winning environment that I enjoyed coming to work every day."

"And so rather than work on hypotheticals [with the Leafs] we try to control what we can control," Shanahan continued. "Which is we want this to be the kind of place that – similar to like I just said – where I was in an organization at one point in my life where players knew that they could get more if they went to unrestricted free agency and knocked on all 30 doors, but instead we want to create an environment here in Toronto where players want to stay and they want to grow up together and have an era of hockey together."

Matthews, Marner and Nylander each get a say in whether that actually happens.

With that in mind, it was interesting to hear Dubas tell TSN’s Bob McKenzie this week that it wasn’t “all too likely” he’d reach extensions with Matthews and Marner before the start of this season.

His top priority at the moment is obviously getting Nylander signed to another contract before the Leafs report for medicals next Thursday, but the GM is taking on some risk by allowing the team’s other two young stars to start playing out the final year of their entry-level contracts.

On one hand, it buys some time. More time for Dubas to sell everyone on the “we before me” philosophy. More time to ascertain exactly where the NHL’s salary cap is headed in 2019-20 and beyond.

However, it also gives the players an opportunity to strengthen their bargaining positions. And what an opportunity this season presents them.

Matthews led all NHL regulars in goals per 60 in each of his first two years, so it’s no stretch to suggest that he could push for major individual hardware in a third season that includes more power-play time, a deeper Leafs forward group around him and, perhaps, better health.

It’s hard to imagine the price going down next summer.

As it is, Matthews has already built a case to land somewhere between Jack Eichel ($10-million AAV) and Connor McDavid ($12.5-million AAV) on an eight-year deal. The $11-million mark seemed like a reasonable spot to land since it would place him alongside new teammate John Tavares for highest paid on the roster.

Marner is looking at all kinds of contractual upside after seasons of 61 and 69 points. Not only did his production trend in an upward direction throughout the second half of last year, he’s also expected to land on a line with Tavares in Year 3.

There’s no harm for him in waiting for that next deal.

None of this will be news to the Leafs front office, which is why their approach is a touch surprising. The belief is that they were open to doing extensions at a discount this summer. The conversations didn’t turn into any team-friendly contracts.

Of course, Dubas could still revisit things with Matthews and Marner after wrapping up Nylander’s deal. There is plenty of time at his disposal.

However, given the quality of players we’re talking about and the kind of season expected in Toronto, time could make a tough task even taller.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.