Beyond Headlines: Nylander, Maple Leafs reaching uncharted territory

Ron MacLean, Nick Kypreos, Chris Johnston and Elliotte Friedman have an update for the William Nylander contract saga with the Toronto Maple Leafs, have news out of Pittsburgh and much more.

What must William Nylander be thinking now?

More than eight weeks after his Toronto Maple Leafs teammates reported for training camp, less than three weeks until he needs a contract in order to be eligible for NHL play this season and soon to be the subject of very legitimate trade speculation …

The mind must be moving fast.

So far, Kyle Dubas has been patient enough to take things slowly with his unsigned 22-year-old winger. The fact he is only now just starting to gauge the Nylander trade market, as Elliotte Friedman reported on our “Headlines” segment Saturday, underscores the notion that the Leafs GM has been focused on one outcome and one outcome only throughout this saga.

Getting Nylander back in his own lineup. It simply may not be possible.

Now, gathering information for a potential trade shouldn’t be confused with certainty that a blockbuster is about to take place. It behooves Dubas to get a complete picture of the landscape he’s operating in before making any decisions that could set the tone for his entire tenure as Leafs GM.

The team has taken a reasonable position during these negotiations based on the comparables it is working from, but it hasn’t made much headway with Camp Nylander. The player’s father, Michael, is believed to be exerting considerable influence over his end of the talks and the former NHLer is no stranger to standing his ground come contract time (multiple messages to Michael Nylander from Sportsnet have gone unreturned in recent weeks).

In fact, there’s scuttlebutt Camp Nylander recently turned down an offer matching the David Pastrnak deal — $40-million over six years — although that rumour was denied over the weekend.

At minimum, there’s considerable skepticism about whether they’d take it.

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William Nylander needs to get his signature on a filed contract by 5 p.m. ET on Dec. 1 to play in the NHL this year — as per Section 11.4 of the collective bargaining agreement, which was created after Michael Peca sat out the entire 2000-01 season while in a dispute with the Buffalo Sabres.

The deadline for signing Group 2 free agents was created to discourage that from happening again by bringing negotiations to a head early in the year. So far it’s worked. According to information provided by Dominik Zrim of capfriendly.com, just 20 unsigned RFAs in the last decade have agreed to a new deal between Oct. 1 and Dec. 1, with only a handful even getting beyond the first week of the regular season:

Nov. 22, 2011: Kyle Turris, Arizona (2 years, $1.4M AAV)
Nov. 7, 2016: Jacob Trouba, Winnipeg (2 years, $3M AAV)
Oct. 27, 2016: Hampus Lindholm, Anaheim (6 years, $5.25M AAV)
Oct. 26, 2015: Mattias Ekholm, Nashville (6 years, $3.75M AAV)
Oct. 23, 2017: Andreas Athanasiou, Detroit (1 year, $1.85M AAV)
Oct. 18, 2018: Nick Ritchie, Anaheim (3 years, $1.64M AAV)
Oct. 15, 2014: Eric Gelinas, New Jersey (1 year, $900,000 AAV)
Oct. 14, 2016: Rickard Rakell, Anaheim (6 years, $3.8M AAV)
Oct. 11, 2016: Rasmus Ristolainen, Buffalo (6 years, $5.4M AAV)
Oct. 11, 2016: Nikita Kucherov, Tampa Bay (3 years, $4.766667 AAV)
Oct. 10, 2016: Johnny Gaudreau, Calgary (6 years, $6.75M AAV)

This list tells us a couple things:

Very few players (and teams) have the stomach for the kind of standoff the Leafs and Nylander are currently engaged in. Short-term bridge contracts are usually there to provide a life raft to common ground.

Trades are rarely needed to resolve these issues. Turris was dealt to Ottawa within a month of signing with the Coyotes in 2011, but otherwise everyone else remained with the same organization throughout his next contract.

The Nylander case is approaching uncharted territory and his days as a Leaf could be numbered as a result. You don’t get as far down this road as he has without realizing it’s a possibility, but the Swede also needs to be cognizant of the fact Toronto might simply stand pat and hang on to his NHL rights if he chooses not to sign by Dec. 1 because it owns them until he’s 27.

Talk about an uncertain future.

This week Shea Theodore told me that the uncertainty of a contract-less summer with the Vegas Golden Knights had him phoning his agent every day for updates. He signed a $36.4-million, seven-year extension on Sept. 25 — leaving enough time to play two exhibition games — and can’t imagine how it would feel to still be waiting for a deal almost 20 games into the regular season.

It’s a feeling only Nylander knows now. It can’t be comfortable.

PLAYOFFS? PLAYOFFS!

Another week and another update on what an expanded playoff format might look like for the NHL. There are teams who are very keen on this concept.

Brian Burke continues to think it’s stupid. He was so thrilled that our “Headlines” panel devoted more time to the topic on Saturday night that he’s threatening to bring in one of his daughter’s participation medals from soccer next week.

I don’t think he’s kidding, either. It might be the first show-and-tell session in the history of Hockey Night in Canada.

Still, the playoff expanders dream on. One solution they’ve proposed for navigating travel issues is having the best-of-three play-in series hosted entirely in the city of the higher seed starting the Sunday after the regular season — with No. 7 welcoming No. 10, and No. 8 entertaining No. 9 in each conference.

After Friedge discussed the idea during our segment, ace Finnish reporter Sami Hoffren reached out to inform us that the SM-liiga in his homeland has been using that very model since 2004.

It’s played to mix results in Finland, according to young Sami, with some dubbing it the “pity playoffs.”

Now that’s a description Burkie can get behind.

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COACH Q

Some interesting stuff from Nick Kypreos on the future of Joel Quenneville following his firing by the Chicago Blackhawks.

Most notably, Kyper reported that Coach Q is ready to work again immediately but unwilling to sign up for the Mike Babcock plan by taking over a team in need of a massive roster overhaul before it is ready to contend. At age 60, he’s eight years older than Babcock was when hired by the Maple Leafs in 2015, so it makes sense.

Any team hiring Quenneville between now and the end of next season would also be required to assume a considerable portion of his annual $6-million salary as part of an offset deal worked out with Chicago.

Realistically, that means we’re talking about a select few potential landing spots for a man bound for the Hockey Hall of Fame.

However, a little birdie wonders: Might the native of Windsor, Ont., rethink his position if the Detroit Red Wings ever come calling?

HOTSAM BATCHO

Thomas Chabot is not Erik Karlsson. He shoots left, not right, and approaches the game in a completely different manner than the two-time Norris Trophy winner.

But the 21-year-old has made Karlsson’s departure just a little bit easier to stomach in the nation’s capital — registering a point in 14 of 17 games for the Ottawa Senators this season while leading all NHL defencemen with 22 points overall.

What’s more, this remarkable start to the year likely wouldn’t have happened had Karlsson not been dealt to San Jose on the opening day of training camp. That freed up minutes Chabot never would have received otherwise.

“I won’t lie: We’re not in a position to not have him play against the better players,” said Senators coach Guy Boucher.

Chabot played 28:49 in a game against Vegas this week. He had nine shots on goal against New Jersey two nights earlier, making him just the seventh age-21-and-under defenceman in the last decade to accomplish that feat — joining Karlsson, Zach Werenski, Drew Doughty, Aaron Ekblad, Matthew Dumba and Zach Bogosian.

He’s a great skater who is getting a better feel for when he can hang on to the puck and make plays.

“He’s able to do outstanding things, but what’s extraordinary is when a young gentleman like that decides to do the simple, ordinary things very well, over and over,” said Boucher. “In the end that’s extraordinary because young guys usually have a tendency to try to do extraordinary things and that’s when turnovers happen, big mistakes. That’s what he’s not doing and that’s exactly why he’s getting all these points.”

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COURTING KIRILL

Question: What’s the only thing more valuable to a NHL team than a difference-making forward? A difference-making forward playing on a below-market contract.

That helps explain Paul Fenton’s decision to travel to Russia and Finland this month to spend time with a Minnesota Wild prospect he can’t bring to North America until at least the 2020-21 season. His name? Kirill Kaprizov, a star for the Russian team at the Pyeongchang Olympics and a point-producing winger for CSKA Moscow in the KHL.

Fenton recently had dinner with Kaprizov and agent Dan Milstein in Moscow — continuing a courtship that began under former Wild GM Chuck Fletcher with a player Minnesota selected in the fifth round in 2015.

Kaprizov doesn’t have any out clauses in his current KHL contract, according to Milstein. But should he chose to come to Minnesota when it expires in 2020 he would be required to sign a two-year entry-level contract. That could be a cap-friendly addition for the team. Worth a few long trips, anyway.

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