William Nylander

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Which NHL GM has toughest job this summer?

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Every general manager has an extremely difficult job when trying to assemble a championship contending team.

No matter the sport it is a daunting task that requires vision, a plan, an ability to actually perform that plan, having the right people around you, and an understanding of not just where the league and their own team is today, but where all of that is headed in future seasons. It requires great scouting, an eye for talent, asset management, a lot of luck, and countless other factors to get their team to a championship level.

Even when all of those things work together in near perfect unison they are still more likely to fall short of their ultimate goal (a championship) than they are to achieve it.

With the NHL offseason officially underway, the league’s 31 general managers are beginning the process of putting their vision into practice, and while they all have a difficult job in front of them not all of their jobs are created equal. Some of them have significantly taller mountains to scale over the next couple of months. Some out of their own creation, and others out of the circumstances and hands they have been dealt.

These general managers are part of that group and have what will almost certainly be the toughest offseason jobs ahead of them.

Ken Holland, Edmonton Oilers

It is a testament to how bad and completely incompetent the previous front office was that Holland is walking into a situation where he has two of the NHL’s top-four scorers from this past season (Connor McDavid and Leon Draisaitl), both still not even in the prime of their careers yet and signed to long-term contracts, and your first reaction to his situation is, “wow, this team seems like it is light years away from contending.”

The Oilers have missed the playoffs in 12 of the past 13 seasons, including three of the first four years of McDavid’s career, having completely wasted what might be some of the best and most dominant hockey he ever plays (at least offensively).

They are a team that plays at the level of an early 1990s expansion team when their two-headed monster of McDavid and Draisaitl is not on the ice, they need an overhaul on defense, a ton of depth at forward, and a goalie. And Holland is likely going to have less than $10 million in salary cap space to start with.

What his roster lacks in talent it makes up for in bad contracts that are sinking the organization’s ability to build around its two superstars at the top.

Milan Lucic‘s contract is, for all intents and purposes, buyout proof and trading him will require Holland to take on a similarly bad contract in return or give up a far more valuable asset to entice a team to take the remaining $6 million per year cap hit (for four more years!) for a player that has just 54 points over the past two seasons (161 games) with only 43 of them coming at even-strength.

His returning starting goalie, Mikko Koskinen, will be 31 years old on opening night and has just 59 games of NHL experience with a .904 save percentage. He is also signed for three more seasons at $4.5 million per season, a rather lousy house-warming gift from the previous regime on their way out the door.

He has eight defenders under contract for close to $27 million under the cap for this season and doesn’t have a No. 1 or anything close to a top-tier puck-mover among them.

At least three of them (Andrej Sekara, Kris Russell, and Brandon Manning) are legitimate buyout candidates this summer.

There are only a handful of teams with less cap space than the Oilers entering the offseason, and it is not because of the contracts they are paying McDavid, Draisaitl, or even Ryan Nugent-Hopkins at the top.

It is because of the $17 million(!) that is going to Lucic, Russell, Manning, and Koskinen.

Other than that, things are pretty good.

If Holland manages to turn this situation into something positive within two years they should build him a statue.

Kyle Dubas, Toronto Maple Leafs

Dubas’ situation is pretty much the exact opposite of Holland’s because his team is actually … good.

Really good.

Really, really, really good.

Championship contending good.

The problem Dubas and the Maple Leafs are going to run into is the same one they have run into in previous years. That “problem” is that it is a lot easier to go from being a “bad” team to a “good” team than it is to go from being a “good” team to a championship team. Having lost in the first-round of the playoffs three years in a row, including to a divisional rival in Boston in each of the past two seasons, kind of illustrates that. The Maple Leafs can score, they can win a lot of games in the regular season, but there is still a hurdle they have to get over because for as good as they have become, this group still does not have a finish higher than third place in its own division or a playoff series win.

But that is all narrative. When it comes to the actual team building Dubas’ challenge is going to be finding a way to get a contract done with Mitch Marner, one of his team’s best and most important players.

The Maple Leafs certainly do not want to go through a replay of last year’s William Nylander restricted free agency saga, and there is always that (please try not to laugh at the ridiculous suggestion) possibility of an offer sheet from another team (hey, one of these years it could happen again).

Finding the salary cap room for Marner is going to be a challenge as the Maple Leafs are already paying Nylander, Auston Matthews, and John Tavares huge money at the top of the lineup. As I wrote a few months ago, this is not a problem. The Maple Leafs can (and most likely will) compete for a championship with a significant chunk of their salary cap allotment going to the quartet of Matthews, Tavares, Marner, and Nylander.

Before they can get there they have to shed some contracts, specifically the ones belonging to Patrick Marleau and Nikita Zaitsev. The top-four might also cost them a couple of other depth players around the edges, but it is a heck of a lot easier to find another Conor Brown or Kasperi Kapanen than it is to find another Mitch Marner or William Nylander.

Along with that, he is also set to lose a little bit off of his blue line with the pending free agencies of Jake Gardiner and Ron Hainsey, while also dealing with the elephant in the room that is the highly paid head coach whose recent resume hasn’t matched his reputation.

Add in the fact this is all playing out in a hockey market where all reason and logic gets thrown out the window and he not only has a difficult task ahead of him, he is going to be under a constant microscope to get it done.

No matter what he does this offseason he has a playoff team on the ice this season.

Simply being a playoff team is no longer enough in Toronto.

Jarmo Kekalainen, Columbus Blue Jackets

He put together the most successful season in Blue Jackets history by not only getting them to the Stanley Cup Playoffs for the third year in a row (first time the franchise has ever done that), but by putting together a team that shocked the hockey world by sweeping one of the best teams of the modern era (the Tampa Bay Lightning) in Round 1 for the team’s first-ever playoff series win.

He did that by betting big on keeping his own pending free agents (Artemi Panarin and Sergei Bobrovsky) but by acquiring several more at the trade deadline in Matt Duchene and Ryan Dzingel.

It gave Blue Jackets fans their first taste of postseason success and built a ton of excitement around the team.

Now he is facing the possibility of losing all of Panarin, Bobrovsky, Duchene, and Dzingel in free agency, while having only two draft picks (a third-round pick and a seventh-round pick) this year and only five draft pick in the 2020 class.

Do we really need to go any further as to what his challenge here is?

Panarin and Bobrovsky have seemingly had one foot out the door all season and their departures just seem to be a matter of where they go and not if they go, and there is little doubt that Duchene is going to test the open market for his one last shot at another big contract (Nashville seems like a perfect fit for him, right?).

The Blue Jackets will still a decent core coming back with Seth Jones, Zach Werenski, Cam Atkinson, and the constantly improving Pierre-Luc Dubois, but Panarin and Bobrovsky are not players that you just easily replace. They have been impact players and significant pieces of what has been a consistent playoff team the past few years. Bobrovsky in particular is going to be a huge loss because he is not only a two-time Vezina Trophy winner and one of the best regular season goalies of his era, but they do not really have any kind of an internal option that is a sure thing and limited options outside the organization.

Kekalainen did an outstanding job to raise the bar and set a new level of expectation in Columbus this season, but he also left himself in a situation where it is going to be extremely difficult to reach it (or exceed it) this upcoming season.

Jason Botterill, Buffalo Sabres

This seems like a make-or-break year for Botterill in Buffalo.

The Sabres are basically Edmonton-east right now given their consistent lack of success, inability to build around a young franchise player (Jack Eichel), and complete lack of depth.

Also like the Oilers: They recently traded an eventual major award winner (2019 Conn Smythe winner Ryan O’Reilly) for some magic beans. The situation in Buffalo is so bleak right now that probably overpaying winger Jeff Skinner is seen as a win for the organization, and I don’t really mean that to be as critical as it sounds because I do like it. If you are going to “overpay” someone under the cap, you are better off making sure it is a player that might score 40 goals for you and seems to have developed some chemistry with your best player.

But after the Eichel-Skinner duo, and 2018 No. 1 overall pick Rasmus Dahlin, this is a roster that just … well … who in the hell excites you here?

The Sabres are in a division with three powerhouse teams at the top, a team a Florida that is already ahead of them with a better core, more salary cap space to work with, and is probably going to be a destination for top free agents (Panarin and Bobrovsky) this summer.

Oh, and there is also Montreal that missed the playoffs this past year by just two points.

This is, at best, the fifth best team in its own division after years and years and years of rebuilding and entering year three with his finger on the button (and with a new coach) there has to be immense pressure for Botterill to make something out of this mess. He has to do a lot, and he has to do it quickly.

More NHL offseason
Lessons NHL teams should (and should not) learn from the 2019 St. Louis Blues
Capitals trade Matt Niskanen to Flyers for Radko Gudas
Islanders re-sign Jordan Eberle
Binnington’s next contract challenge for Blues
Bruins could look different next 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.

Youth is being served early in Stanley Cup playoffs

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For all the value of postseason experience, youth is off to a nice start in the Stanley Cup playoffs.

Teenage defenseman Miro Heiskanen built on his stellar rookie season in his playoff debut with Dallas, 19-year-old Andrei Svechnikov tried to carry Carolina back from a big deficit, early 20-somethings Mitch Marner and William Nylander continue to be among Toronto’s best players and young Matthew Tkachuk did his part to finally win a playoff game with the Calgary Flames.

The NHL is getting younger and more skilled, and youth is being served in a big way early in the Stanley Cup playoffs. They may not get the attention like Winnipeg’s Patrik Laine or Toronto’s Auston Matthews, but Heiskanen and Svechnikov turned in two of the more impressive playoff performances in recent history for players before their 20th birthdays.

”Some people, it’s hard and some people it’s pretty easy, and those are the people it looks like it’s pretty easy,” Hurricanes forward Teuvo Teravainen said of Svechnikov and fellow Finn Heiskanen. ”They don’t stress too much. They just go out and play and have some fun.”

Svechnikov became the youngest player in 22 years to score twice in a playoff game and the third teen to put up two goals in NHL postseason history after Pierre Turgeon in 1988, Eddie Olczyk in 1985 and Don Gallinger in 1943. The 2018 second overall pick will try to help Carolina even its first-round series against Washington in Game 2 Saturday (3 p.m. ET, NBC).

”There’s not pressure on him,” Hurricanes captain Justin Williams said. ”Just go do it. Go enjoy it. Go have fun. That’s what this time of year is about, and we’re going to need even more from him if we’re going to advance.”

The Stars won in Nashville thanks in large part to Heiskanen’s goal and assist in Game 1 . At 19 years, 266 days old, he became the youngest defenseman in franchise history to score in the playoffs and the fifth teenage rookie defenseman with two points in his postseason debut.

”My 19-year-old year, when it was April, I was drinking beers in my frat basement,” Dallas defenseman Ben Lovejoy said. ”What he is doing is just incredible. It’s so special. He is so good, it is just such a pleasure to watch him play and to be on his team. He’s such an asset. He’s going to do this for 20 years and I can’t wait to watch him.”

Coach Jim Montgomery would love to see Heiskanen and 22-year-old rookie Roope Hintz play like this for several more weeks. Game 2 in Nashville is Saturday (6 p.m. ET, CNBC).

In Boston, the Bruins have to be better in Game 2 (8 p.m. ET, NBC) on Saturday after losing the series opener on home ice. Marner was a big part of that with his two-goal game, including being just the fifth player to score a shorthanded goal on a penalty shot in the playoffs.

[NBC 2019 STANLEY CUP PLAYOFF HUB]

”He’s an elite player in the league at a young age,” Bruins coach Bruce Cassidy said. ”Years ago I remember (people saying about Wayne) Gretzky, ‘Why doesn’t anybody hit that guy?’ Well, it’s not that easy.”

It’s not easy to hit or stop Nylander, either. The 22-year-old Swede scored for the second consecutive game and appears to have solved his late-season dry spell.

”It’s good for me,” Nylander said. ”I’ve been thinking just to hit the net and get it on it.”

In Calgary, Tkachuk’s two goals a series-opening victory against the Colorado Avalanche snapped his six-game goal drought, though the 21-year-old’s agitating ways stuck as much as his scoring. Teammate Andrew Mangiapane, 23, also scored in his playoff debut and the West’s top seed is off and running with Game 2 Saturday night in Calgary (10:30 p.m. ET, NBCSN).

”Now all of those guys have got their first game out of the way, they should get some confidence,” coach Bill Peters said. ”We’ll get better as the series goes along.”

INJURY WATCH

Even in the hockey-speak of upper- and lower-body injuries, playoff time brings an extra cloud of secrecy. Seemingly everyone is day-to-day or a game-time decision.

That’s the case for Carolina defenseman Calvin de Haan, who practiced Friday after missing the past six games with an upper-body injury. Coach Rod Brind’Amour said he hopes de Haan can play ”at some point” and added defenseman Jaccob Slavin was fine after getting a day off for playing a lot of minutes Thursday night.

Boston forward Jake DeBrusk is questionable with the injury that knocked him out of Game 1 against the Maple Leafs. Cassidy said if DeBrusk can’t play, veteran David Backes will go into the lineup.

AP Sports Writers Teresa M. Walker in Nashville and Jimmy Golen in Boston contributed.

Follow AP Hockey Writer Stephen Whyno on Twitter at https://twitter.com/SWhyno

More AP NHL: https://apnews.com/NHL and https://twitter.com/AP-Sports

Maple Leafs take Game 1 against Bruins on the road

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The Maple Leafs limped into the playoffs with a 4-7-3 record to round out the season and rob any chance of Game 1 of their long anticipated series against Boston being played in Toronto. In the end though, it didn’t matter. After working through some late season injuries, the Maple Leafs had all hands on deck and combined they delivered a 4-1 victory over Boston.

While this game certainly wasn’t a blowout by any stretch of the imagination, it was close to the ideal scenario for the Maple Leafs. Most importantly, goaltender Frederik Andersen was great. There were some concerns about fatigue with him late in the season and he didn’t look good in the 2018 series against Boston, but this game would have been very different if he was just okay.

The only time Andersen was beat Thursday night was on a superb power-play goal from Brad Marchand to Patrice Bergeron. That marker gave the Bruins a 1-0 lead and had the potential to set the tone, but Mitchell Marner changed the story.

Marner evened the contest before the first period ended and provided the turning point when he got on a breakaway while the Maple Leafs were shorthanded. He drew a penalty shot that led to Toronto’s game-winning goal.

That narrow 2-1 edge stuck for most of the second period until William Nylander provided Toronto with some much needed breathing room, thanks in part to a laser pass from Nazem Kadri.

Boston ended up out shooting Toronto 21-14 in the second period alone, but the Maple Leafs scored the only two goals in that frame. That 3-1 lead would stick until John Tavares finished Boston off with an empty netter.

The Maple Leafs now have something they never possessed in the 2018 series against the Bruins: The lead. In 2018, the Bruins won the first two games in Boston and while Toronto battled back to force a Game 7, the Maple Leafs never possessed the series lead. Now we’ll see if Toronto can build on its early success or if Boston will come right back in Game 2. Certainly, Boston is too good of a team to be dismissed after just one loss.

Maple Leafs-Bruins Game 2 from TD Garden will be Saturday night at 8:00 p.m. ET on NBC

Ryan Dadoun is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @RyanDadoun.

Can Maple Leafs make salary cap work after signing Nylander?

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After plenty of drama unfolded – particularly among nervous fans – the Toronto Maple Leafs hashed out a six-year deal worth just under $7 million per year for William Nylander.

Fans, coach Mike Babcock, GM Kyle Dubas, Nylander, and hockey media at large let out an exhale. But, for some, the immediate question returned: how are the Maple Leafs going to make this fit under the salary cap for 2019-20 and beyond?

After all, the futures of Auston Matthews and Mitch Marner (and even Jake Gardiner?) held up Nylander’s negotiations, to some extent, in the first place.

During the NHL’s recent Board of Governors meetings, word surfaced that the cap ceiling will be approximately $83 million in 2019-20. That number can change, yet it’s a helpful window for the Maple Leafs to consider. It’s also helpful that it’s a nice bump up from this season’s high mark of $79.5M.

Let’s be honest, though: this would probably be challenging even if the cap was at, say, $90 million.

So, what are the Leafs to do? Let’s try to break things down in different subcategories, with some guidance from the always-helpful site Cap Friendly.

I’ll throw in some of my opinions about who’s especially important to Toronto’s viability, who (to me) is an obvious player to trade, and the guys who stand in the murky middle.

This is a pretty deep dive, so buckle up.

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Anticipated salary cap: Approximately $83 million in 2019-20, up from $79.5M this season.

Committed to cap as of today, via Cap Friendly$56.3M on 12 players. So, Marner + Matthews ($20M) would likely bump it up to at least $76.3M for 14 players.

***

The Core (already signed)

John Tavares, 28, $11 million, 2024-25
William Nylander, 22, $6.962M, 2023-24
Frederik Andersen, 29, $5M, 2020-21
Morgan Rielly, 24, $5M, 2021-22
Nazem Kadri, 28, $4.5M, 2021-22

Notes: Kadri is one of those players some might categorize differently.

To me, though, he’s an absolutely crucial bargain. It’s not just that Kadri can be a second-line center at a very reasonable price; it’s that Kadri is a credible second-line center at just $4.5M. In my book, that makes him a core piece.

Andersen and Rielly stand as absolutely crucial bargains, even more than Kadri. You can quibble about Rielly as a Norris candidate, but for $5M, a player with his skills is a dynamite deal. He’s that much more important on a defensive group that stands as Toronto’s glaring weakness. Andersen cleans up a lot of those messes at a very reasonable price.

Support bargains

Zach Hyman, 26, $2.25M, 2020-21
Connor Brown, 24, $2.1M, 2019-20
Travis Dermott, 21, $863K expires after next season

Notes: Dermott being a good defenseman at an entry-level price is downright critical to the Maple Leafs’ hopes of surviving the pending cap crunch. His cheap deal almost makes him feel like a core piece by context.

These other two forwards are really nice to have, too, particularly Hyman. He’s not lighting the world on fire, yet Hyman’s shown that he can be a very useful top-nine forward. Brown has a 20-goal season to his name (in 2016-17).

That said, it’s not outrageous to wonder if the Maple Leafs might need to part with Brown, in particular, if the squeeze gets boa-like.

Problem/disposable contracts

Patrick Marleau, 39, $6.25M for next season
Nikita Zaitsev, 27, $4.5M, 2023-24
Nathan Horton‘s contract: $5.3M that’s been LTIR bound, expires after 2019-20

Notes: This is where things get awkward, but where work can get done.

It’s obvious that there’s a lot of organizational love for Marleau, particularly from Babcock, as James Mirtle noted for The Athletic about a week ago (sub required).

“He makes you a flat out better human being just by walking by you,” Babcock said.

That piece goes in-depth on how much Babcock and others rave about Marleau’s “intangibles,” but when basically every $100K counts, can you really justify $6.25M for being “good in the room?” Mirtle also breaks down how Marleau’s play is (understandably) decaying, and as we’ve seen with sports, Father Time can slam the door shut on your production with startling speed and cruelty.

That money could easily slot in as Gardiner’s next cap hit, and while Gardiner draws critics, the Maple Leafs need defensemen like him. And those defensemen aren’t exactly growing on trees. Perhaps the Maple Leafs could a) get a veteran presence at the veteran minimum or b) hire a retired player to serve as a mentor, one who doesn’t count against the cap?

If I were in Dubas’ shoes, I’d be looking for creative avenues to take care of this issue right now, but the most likely scenario would be for Toronto to part ways with Marleau during the summer — if at all. Marleau possesses a no-movement clause throughout his deal, so that could end up being a very messy situation. I’m not certain the Maple Leafs can actually pull off trading Marleau, but his deal is a real problem, unless there’s a pending “shady run to the LTIR” in his future. Right, Joffrey Lupul?

(The third year of Marleau’s deal boggled my mind when it was signed, and continues to drive me a little nuts.)

Speaking of messy situations, Horton’s $5.3M has gone to LTIR during his entire “run” with Toronto, as he slotted in to replace a similar nightmare with David Clarkson.

The Maple Leafs could easily LTIR Horton again next summer, although there would be some advantages to getting that off the books earlier, so let’s at least keep his contract in mind. Maybe a rebuilding team could take Horton off of their hands as part of a complex, creative deal? Perhaps it could instead be as simple as the equivalent to the Coyotes taking Marian Hossa‘s contract from the Blackhawks?

The final problem contract of note is that of Zaitsev.

It’s understandable that Toronto gave him that $4.5M cap hit after he scored 36 points and at least survived possession-wise as a rookie in 2016-17, yet it’s been a galling fall from grace for Zaitsev. It’s tough to ponder the possibility that Zaitsev’s presence could push someone far better out, whether that someone is Gardiner or perhaps a solid mid-level free agent defenseman (or a nifty trade target like, say, similarly priced Justin Faulk).

The term of Zaitsev’s contract makes it scarier, and also could make it tougher to move than Marleau, who would only burden a taker’s team through next season.

That said, at 27, there’s a chance Zaitsev could be rehabilitated. Perhaps the Maple Leafs could sell that story (along with offering up some picks as bribery) to a team that might be willing to give him a change of scenery for a price?

***

Whoppers

Auston Matthews, 21
Mitch Marner, 21
Jake Gardiner, 28

Notes: All three of these players’ situations justify their own posts.

Matthews and Marner, obviously, are rising stars. The toughest questions there revolve around how much they’ll cost, and if the Leafs can get them both to sign long-term rather than accepting “bridge” deals.

Placing myself back in Dubas’ (shinier, nicer, more expensive) shoes, I’d do whatever I could to extend both Matthews and Marner now rather than later.

At best, both forwards’ perceived values will remain the same, but there’s a strong chance that each guy could only earn more dollars with a big run this season. That only inflates if the Maple Leafs make a (very plausible) deep run in the 2019 Stanley Cup Playoffs.

Also, every day that passes brings opportunities for other contracts to serve as dangerous comparables. What if Patrik Laine breaks the bank, like, tomorrow? Mikko Rantanen might want to settle his extension now, and that deal won’t be cheap.

Right now, Connor McDavid‘s $12.5M serves as something of a logical barrier for Matthews. Let’s not forget that McDavid left some money on the table, and maybe the next wave of prominent free agents won’t be so generous.

The Maple Leafs would also gain some cost certainty if they locked up Matthews and Marner now.

Oh yeah, Toronto would also avoid the threat of an offer sheet. That’s not totally irrelevant, especially since the Islanders would probably lick their chops at the prospect of getting some Tavares-revenge.

Gardiner is a tough call, and he might be the one who needs to go down to the wire. How much is he worth? How large is the fall from Gardiner to replacement-level players? Consider two possibilities in the system:

A couple defensive prospects of interest

Rasmus Sandin, 18
Timothy Liljegren, 19

Notes: Here are two defensemen who could at least conceivably step into a spot or two in 2019-20, although it’s fair to wonder if they’d truly be ready.

Both Swedes are first-rounders, with Sandin going 29th overall in 2018, while Liljegren was selected 17th in 2017. Sandin’s getting his first bit of seasoning in the AHL; Liljegren is in his second campaign with the Toronto Marlies.

As of this writing, the Maple Leafs are especially needy when it comes to right-handed defensemen (both Gardiner and Rielly are lefties), so that factor and Liljegren’s additional year of seasoning lights more of a path for the slightly older prospect.

Pending RFAs potentially playing their way out of Toronto

Kasperi Kapanen, 22
Andreas Johnsson, 24
Garret Sparks, 25

Notes: Kapanen and Johnsson emerging serves as a double-edged sword. It’s great to see a prospect stick after struggling to fight through a deep forward corps (Kapanen), and it’s also awesome to find a diamond in the rough (Johnsson). But will they play so well that they become unaffordable?

Similarly, Sparks has served as a suitable backup at a dirt-cheap price.

Assorted expiring contracts

Tyler Ennis, Ron Hainsey, Par Lindholm, Igor Ozhiganov

***

Potential solutions, closing thoughts

Phew, that’s a lot to chew on, right?

To review: the Maple Leafs have some issues to deal with, and a slew of questions to answer. Are they really going to allocate that much cap space to Marleau, and can they afford to just deal with Zaitsev’s expensive struggles? Does Gardiner rank as one of those cap casualties they just need to deal with? Is there any chance that Matthews and/or Marner would sign now, and would that be the wiser course?

The good news is that Dubas & Co. have shown early acumen when it comes to unearthing cheap options to fill in blanks. An analytics-driven mindset might help them spot more diamonds in the rough, or merely identify cheaper options that won’t drag the team down too much when their stars aren’t on the ice.

There’s also another key bullet in the chamber: veterans who might sign for cheap in hopes of chasing a Stanley Cup.

If you’re Anton Stralman, maybe you’d give the Maple Leafs a discount to be part of something special? Perhaps a similar thought would occur to Tyler Myers, who would have just completed a $38.5M contract?

(Less-ideal scenarios would involve signing, say, Dan Girardi or Babcock favorite Roman Polak … so let’s move on.)

This situation can work out in about a million different ways, and the possibilities honestly leave my brain overflowing like the old logo for “Scattergories.”

The thing is, these are good problems to have. The Maple Leafs have Tavares, Nylander, Andersen, and Rielly under contract for some time. They seem resolute in keeping, at minimum, Matthews and Marner. Almost every other NHL team would practice dark arts to land that foundation.

Can Dubas hit all the right notes to keep this roster competitive, even once the bill comes? We’ll need to wait and see, but the Maple Leafs stand as a team to watch, and are likely to stay that way for a long time.

If you want to ponder how you’d handle various situations yourself, you could always fiddle with Cap Friendly’s Armchair GM tool. Warning: your self-confidence may fall as a result, because a lot of this counts as “easier said than done.”

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.

Nylander, Maple Leafs agree to six-year, $41.4M extension

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With minutes to go before the 5 p.m. ET signing deadline, the William Nylander contract drama came to an end.

Nylander and the Toronto Maple Leafs have agreed on a six-year pact worth $41.4M. According to the team, because he’s signing two months into the season his salary cap hit for 2018-19 will be $10.2M. Here’s a full breakdown:

Come July 2, 2019, Nylander becomes a pretty attractive trade piece to other teams who want to take advantage of a potentially cap-strapped Maple Leafs team.

The deal also includes a 10-team no-trade cause in the final year, per McKenzie. He was ineligible for one in the first five years of the contract.

Had Nylander not signed by Saturday’s deadline he would have been ineligible play in the NHL for the rest of the season and the Maple Leafs would have retained the restricted free agent’s rights.

“We think Willie is going to be here and we think Willie is going to be here for a long time,” said Maple Leafs head coach Mike Babcock this week. “We think he is going to be a career Leaf. That’s what we think. That’s what we believe.”

In 185 games with the Maple Leafs, Nylander has scored 48 goals and recorded 135 points. He’ll be a nice addition to the NHL’s fourth-highest scoring team (93 goals) as they continue to eye a Stanley Cup run this spring.

Reports had the negotiations falling somewhere between a bridge deal for about three years and a longer-term extension of six, which they settled on. Nylander had been skating with European teams while both sides tried working on a deal.

That’s now one contract down and a few more big ones to go for general manager Kyle Dubas. Next summer Auston Matthews, Mitch Marner, Kasperi Kapanen are the team’s big name RFAs who need new deals, and Jake Gardiner will be unrestricted. It will be interesting to see if any of them are tough negotiations like Nylander was and how that affects the team’s summer plans.

MORE: Your 2018-19 NHL on NBC TV schedule

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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.