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Can Maple Leafs make salary cap work after signing Nylander?

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The Boston Bruins and Chicago Blackhawks will take their skates outside to historic Notre Dame Stadium in the Winter Classic on New Year's Day.

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.
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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?
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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
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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.