Maple Leafs and Nylander: Contract deadline, trade talk, more

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Despite Saturday’s 5 p.m. ET contract deadline being achingly close, it’s still any outsider’s guess what will happen between the Toronto Maple Leafs and William Nylander. For all we know, both the player and team aren’t 100-percent sure, either.

It’s also unclear how the Maple Leafs’ pending salary cap crunch will impact Nylander’s future with the team beyond 2018-19.

Let’s try to wade through the many ins and outs of this situation, with the best information currently available. If your head starts spinning, at least realize that you’re not alone.

Various rumblings about what a contract might look like with Toronto

During an NBCSN appearance on Wednesday, Bob McKenzie provided one of many possible windows for a Nylander contract. As opposed to many other situations where it’s difficult to hash out a deal, McKenzie reports that Nylander would actually not prefer a shorter “bridge” contract. Instead, he’d lean toward six years. McKenzie placed Toronto’s preferred cost at $6.7 million per year, while Nylander might want something closer to $7M.

This jives with figures from Sportsnet’s Chris Johnston, who somewhat recently placed a possible compromise at $6.9M per year.

(Such reports bring to mind a somewhat amusing cacophony. On one hand, it feels absurd that a few hundred thousand would make such a difference when you’re talking about multiple millions. On the other hand … most of us would absorb multiple slashes to our softest parts for that difference alone.)

Do note that McKenzie at least floated the possibility of what would be closer to a “bridge” deal, even if it doesn’t sound like this would be Nylander’s first choice:

One factor to keep in mind is that, if the Maple Leafs reach a deal with Nylander before that Saturday dinner deadline, it would be “prorated” since we’re already more than a quarter through the 2018-19 season. Cap Friendly broke down how such variables might play out:

Basically, either a three-year or six-year deal (or other permutations) could be a great fit for the Maple Leafs. The 2018-19 year of a contract would feature a significantly increased cap hit (which works for Toronto, as they’re flush this season before the crunch hits) and then years two and on would be deflated.

What if there’s no deal at all?

Nylander wouldn’t be able to play in the NHL in 2018-19, thus possibly forcing him to play in an overseas league (or, if he doesn’t want to risk injury, not play at all). In that McKenzie video, you’ll note that Nylander wouldn’t gain any additional leverage if he sat out a season, as he’s not yet eligible for salary arbitration.

A couple weeks ago, Pierre LeBrun brought up a different – though difficult to imagine, even now – Feb. 25 deadline in an article for The Athletic (sub required).

In that scenario, the Leafs would trade Nylander’s rights. Such a maneuver would essentially only open up possibilities for teams not making the playoffs, as Nylander would still be unable to play in the NHL in 2018-19.

Seems unlikely, right? It’s worth mentioning, especially as we move to more plausible trade scenarios.

Talking trades

That Feb. 25 deadline is part of a potential trade deadline. Let’s start with the earliest link in that chain: moving Nylander’s rights before Saturday’s 5 p.m. deadline.

Multiple reporters (including LeBrun) indicate that the Maple Leafs would prefer to sign Nylander, not trade him. Even so, Toronto GM Kyle Dubas is at least touching bases. TSN’s Frank Seravalli points to a specific team that’s been in contact: the Philadelphia Flyers.

Landing a prime winger like Nylander would certainly make a boatload of sense for the Flyers, particularly if they wanted to make a statement after firing a shocked Ron Hextall from his GM position.

Theoretically, another team would be able to add Nylander with fewer worries about the future. On the other hand, few teams really have the cap space to easily add Nylander’s prorated deal in, as discussed earlier in this post. During the latest edition of TSN’s Insider Trading, McKenzie notes that the trade market has been “shrinking” because of those cap concerns.

So, that would make Nylander tougher to trade … for this season.

What if the Maple Leafs sign Nylander, only to trade him in the future, even if he gets a longer-term deal? Sportsnet’s Elliotte Friedman grimly stated on “Tim & Sid” that he believes that Nylander won’t be a Maple Leaf after this season, and pegged the 2019 NHL Draft as possibly the latest he’d be traded:

One can debate the likelihood of any trade happening, but there are a few potential windows to consider. A quick “tl;dr” recap, then:

Potential path 1: Before Saturday’s signing deadline.
Potential path 2:Feb. 25 – no signing happens, but a team could trade for his rights for 2019-20 and beyond.
Potential path 3: Nylander signs a contract with Toronto, only to be traded by the 2019 NHL Draft?
Potential path 4: No trade at all?

The elephants in the room

Most likely know this full well, but 2019-20 and beyond looms as a conundrum for the Maple Leafs with good reasons: Auston Matthews and Mitch Marner need new contracts.

That Insider Trading segment noted that many big-ticket RFAs are preferring to wait until 2018-19 ends to really negotiate, rather than signing extensions now.

In the case of Marner, a proactive extension might not be especially cheap. Even at a shorter four-ish year commitment, a $10M number is being thrown around. Considering how many points Marner could put up during a full season as John Tavares‘ wingman, it’s no surprise that he could be pricey.

Matthews stands as almost certainly an even more expensive proposition. Could Toronto convince him to match Tavares’ $11M, or somewhere close? Would Connor McDavid‘s slight discount $12.5M serve as a ceiling? How will potential deals for other stars like Patrik Laine affect Matthews’ bargaining?

All of those questions – not to mention what to do with Jake Gardiner, and which steps to take to make the team better – don’t just plague the Maple Leafs for the future. They must consider them now.

Such a cap crunch might force Toronto’s hand with Nylander, even if they truly believe he’s worth paying in the $7M range. That’s especially true if, say, they can’t unload Nikita Zaitsev‘s deal off ($4.5M through 2023-24[!]) to a lower-end team at a price, or do something similar with the last year of Patrick Marleau‘s $6.25M cap hit.

Happy place

Of course, there’s also a possibility that the Maple Leafs have no intention to trade Nylander at all.

Let’s not forget that other teams have handled cap crunches to the point that they’ve at least retained their key guys. The Lightning defied odds in signing Steven Stamkos, Nikita Kucherov, and Victor Hedman; in many cases, Tampa Bay landed them below-market-value, sometimes by leveraging RFA years. While it’s true that the Blackhawks couldn’t walk the tightrope forever, they won three Stanley Cups in part because they were able to walk that thin line for a long time. Some of us thought they’d collapse much sooner.

Is it that outrageous to imagine the Maple Leafs making this work?

Granted, the recent history of tough contract holdouts and strained situations have often resulted in eventual trades. P.K. Subban feels like the most prescient example, yet there are others.

The Maple Leafs are run by what seems to be smart people, and Mike Babcock recently stated that he expects Nylander to be a “career Leaf.”

It’s not that difficult to imagine the Maple Leafs bribing someone to take a nonessential contract in exchange for assets or other considerations. They did it with David Clarkson‘s ghastly deal, and it’s perfectly plausible that they can make it happen again.

Let’s not forget that the salary cap has been rising, too. Last season, the ceiling was $75M, while it’s up to $79.5M for 2018-19. A comparable jump for 2019-10 might just give the Maple Leafs enough breathing room to afford Nylander, Matthews, Marner, Tavares, Frederik Andersen, and maybe even a few other players above a replacement level.

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Complicated stuff, right?

The bottom line is that it’s very difficult to predict how this will play out, especially when you zoom out beyond the already-tricky deadline Nylander and the Maple Leafs face on Saturday at 5 p.m. ET.

For fans of the sport and/or those interested in team-building, it should be almost as fascinating to watch as it is to watch this blazingly talented Maple Leafs team actually play games.

What would you do if you were running the Maple Leafs? What do you expect to find out? We won’t have to wait long for actual answers.

At least, for some answers.

MORE: Your 2018-19 NHL on NBC TV schedule

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.

Capitals re-sign Vrana for two years, $6.7 million

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Washington Capitals general manager Brian MacLellan took care of his biggest remaining offseason task on Tuesday afternoon when he re-signed restricted free agent forward Jakub Vrana to a two-year contract.

The deal will pay Vrana $6.7 million and carry an average annual salary cap hit of $3.35 million per season.

“Jakub is a highly skilled player with a tremendous upside and is a big part of our future,” said MacLellan in a statement released by the team. “We are pleased with his development the past two seasons and are looking forward for him to continue to develop and reach his full potential with our organization.”

[ProHockeyTalk’s 2019 NHL free agency tracker]

Vrana was the Capitals’ first-round pick in 2014 and has already shown top-line potential in the NHL. He took a huge step forward in his development during the 2018-19 season, scoring 24 goals to go with 23 assists while also posting strong underlying numbers. He is one of the Capitals’ best young players and quickly starting to become one of their core players moving forward.

It is obviously a bridge contract that will keep him as a restricted free agent when it expires following the 2020-21 season. If he continues on his current path he would be in line for a significant long-term contract that summer.

With Vrana signed the Capitals have under $1 million in salary cap space remaining. They still have to work out new contracts with restricted free agents Christian Djoos and Chandler Stephenson. Both players filed for salary arbitration. Djoos’ hearing is scheduled for July 22, while Stephenson has his scheduled for August 1. If the Capitals want to keep both on the NHL roster on opening night they may have to make another minor move at some point before the start of the regular season.

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.

Donato gets two-year, $3.8 million extension from Wild

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Ryan Donato took advantage of a bigger opportunity with the Minnesota Wild and earned himself a raise on Tuesday.

The Wild announced that they have extended the 23-year-old Donato with a two-year, $3.8 million contract. That $1.9 million annual salary will be a bump from the $925,000 he made during the 2018-19 NHL season.

Following a February trade that sent Charlie Coyle to the Boston Bruins, Donato saw his ice time rise over three minutes under Bruce Boudreau and that resulted in four goals and 16 points in 22 games with Minnesota. Unable to carve out his own role in Boston, Donato struggled offensively with six goals and nine points in 34 games before moving.

“I definitely learned the business side of it, for sure,” Donato said in April. “One thing I learned, in Boston and here, it’s a game of ups and downs. More than college, more than any level, there’s a lot of ups and downs. It’s been an emotional roller coaster the whole year, but definitely over the last couple months it’s settled down quite a bit.”

[ProHockeyTalk’s 2019 NHL free agency tracker]

Donato, who was a restricted free agent and will remain one when his contract expires after the 2020-21 season, continued his production in the American Hockey League’s notching 11 points in 14 games between the end of the Iowa Wild’s regular season and the Calder Cup playoffs.

“It’s all about opportunity in this league,” Donato said. “If I can get myself into scoring positions playing with the high-end veteran players we have here, that have been known to find guys in scoring positions, then I’m a guy that can bury it.”

The Wild have high hopes for next season as they expect to be a playoff team coming out of what will be a very, very competitive Central Division. General manager Paul Fenton added Ryan Hartman and Mats Zuccarello to boost the team’s offense which finished fourth-worst in the NHL in goals per game (2.56). Donato will be expected to be a key contributor.

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Sean Leahy is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @Sean_Leahy.

Trade: Blackhawks send Anisimov to Senators for Zack Smith

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Artem Anisimov‘s name has been floating in trade speculation for more than a year now, and on Tuesday afternoon the Chicago Blackhawks finally moved him.

The Blackhawks announced they have traded Anisimov to the Ottawa Senators in exchange for forward Zack Smith. It is a one-for-one deal that will probably make a bigger impact on both team’s financial situations than on the ice.

Both players are 31 years old, have two years remaining on their current contracts, and are coming off of somewhat similar seasons in terms of their performance. Anisimov scored 15 goals and 37 points in 78 games for the Blackhawks this past season, while Smith had nine goals and 28 points in 70 games for the Senators.

[ProHockeyTalk’s 2019 NHL free agency tracker]

So what is important here for both teams? Money, obviously.

For the Blackhawks, the Anisimov-for-Smith swap saves them a little more than $1 million against the salary cap as they go from Anisimov’s $4.5 salary cap hit to Smith’s $3.25 number. For a team that is consistently pressed against the cap and still has a ton of big-money players, every little bit of extra space helps. Especially as they have to work out new deals for Alex DeBrincat and Dylan Strome over the next year.

The Senators, meanwhile, had a different set of problems.

They were still sitting under the league’s salary floor before the trade and are now finally above it.

Anisimov’s contract not only gets them over the floor, but because the Blackhawks have already paid Anisimov’s signing bonus for this season the Senators actually owe him less in terms of actual salary, which is also probably an important factor for a team that is seemingly always in a cost-cutting and money-saving mode.

The Blackhawks have been extremely busy this offseason making multiple changes to their roster after a second straight non-playoff season. Along with acquiring Olli Maatta and Calvin de Haan in trades to try and upgrade their defense, they also signed goalie Robin Lehner in free agency and brought back veteran forward Andrew Shaw.

This past week they traded former first-round pick defender Henri Jokiharju to the Buffalo Sabres for Alex Nylander.

Related: Blackhawks shaping up as NHL’s biggest wild card

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.

Werenski, McAvoy should be in line for huge contracts

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When it comes to the NHL’s restricted free agent market this summer most of the attention has been directed at forwards Mitch Marner, Mikko Rantanen, and Sebastian Aho. They are the stars, the big point-producers, and in the case of Aho, the rare player that actually received — and signed — an offer sheet from another team, only to have the Carolina Hurricanes quickly move to match it. For now, though, let’s shift the focus to the blue line where there are a few more big contracts still to be settled this summer with Jacob Trouba, Charlie McAvoy, Zach Werenski, and Ivan Provorov all waiting on new deals from their respective teams.

The two most intriguing players out of this group are Columbus’ Werenski and Boston’s McAvoy because they are already playing at an elite level among NHL defenders.

Just how good have they been?

Both are coming off of their age 21 seasons and have already demonstrated an ability to play at a top-pairing level on playoff caliber teams.

Since the start of the 2007-08 season there have only been four defenders that have hit all of the following marks through their age 21 season:

  • At least 100 games played
  • Averaged at least .50 points per game
  • And had a Corsi Percentage (shot-attempt differential) of greater than 52 percent at that point in their careers.

Those players have been Erik Karlsson, Drew Doughty, Werenski, and McAvoy.

That is it.

Pretty elite company.

Based on that, it seems at least somewhat reasonable to look at the contracts Karlsson and Doughty received at the same point in their careers when they were coming off of their entry-level deals.

They were massive.

Karlsson signed a seven-year, $45.5 million deal with the Ottawa Senators, while Doughty signed an eight-year, $56 million contract. At the time, those contracts were worth around 10 percent of the league’s salary cap. A similarly constructed contract under today’s cap would come out to an annual cap hit of around $8 million dollars, which would be among the five highest paid defenders in the league.

[ProHockeyTalk’s 2019 NHL free agency tracker]

Are Werenski and McAvoy worth similar contracts right now? They just might be.

The argument against it would be that while the overall performances are in the same ballpark, there are still some significant differences at play. Karlsson, for example, was coming off of a Norris Trophy winning season when he signed his long-term deal in Ottawa and was already on track to being one of the best offensive defensemen ever (he was already up to .68 points per game!). Doughty, meanwhile, was a significantly better defensive player than the other three and had already been a finalist for the Norris Trophy.

Neither Werenski or McAvoy has reached that level yet, while Werenski also sees a pretty significant drop in his performance when he is not paired next to Seth Jones, which could be a concern depending on how much value you put into such a comparison. It’s also worth pointing out that Jones sees a similar drop when he is not paired next to Werenski, and that the two are absolutely dominant when they are together.

But do those points outweigh the production and impact that Werenski and McAvoy have made, and the potential that they still possess in future years?

What they have already accomplished from a performance standpoint is almost unheard of for defenders of their age in this era of the league. It is also rare for any player of any level of experience.

Over the past three years only 15 other defenders have topped the 0.50 points per game and a 52 percent Corsi mark. On average, those players make $7 million per season under the cap, while only three of them — Roman Josi, Shayne Gostisbehere, and Erik Gustafsson — make less than $5 million per year. Josi is also due for a huge raise over the next year that will almost certainly move him into the $7-plus million range as well.

Bottom line is that the Blue Jackets and Bruins have top-pairing defenders on their hands that still have their best days in the NHL ahead of them. There is every reason to believe they are on track to be consistent All-Star level players and signing them to big deals right now, this summer, will probably turn out to be worth every penny.

Related: Bruins face salary cap juggling act with McAvoy, Carlo

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.