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NHL Free agency: Most long-term contracts will end in trade or buyout

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Exactly six years ago Friday, the Toronto Maple Leafs made one of the most infamous free agent signings in the salary cap era when they inked David Clarkson to a seven-year, $36.75 million contract. It was a dubious signing from the very beginning due to Clarkson’s age (he was already 29 years old) and lack of consistent, top-line production in the NHL. Adding to the absurdity was the reception of the contract in Toronto (comparing him to Wendel Clark) and the way then-general manager Dave Nonis defended the signing from any and all criticism by saying, “I’m not worried about six or seven right now. I’m worried about one. And year one, I know we’re going to have a very good player. I believe that he’s got a lot of good years left in him.”

How did that work out?

In year one Clarkson scored five goals in 60 games, was a colossal bust, and was then traded to the Columbus Blue Jackets halfway through year two of the contract for Nathan Horton, another free agent bust from the same offseason whose career would be derailed and ultimately ended by injury. The Maple Leafs knew Horton would never play again and the whole trade was nothing more than a way to shed an albatross contract that looked to be a mistake from the start. It was an obvious — and ultimately legal — circumvention of the league’s salary cap.

Clarkson’s contract is far from the only one that has gotten general managers in trouble for signing a player for too many years in free agency. Almost every time the justification is similar to the one Nonis gave for the Clarkson signing: We’re not worried about four or five years, we just want to win right now.

Most of them never win “right now,” and almost all of them are looking for a way out within two years.

Between the summers of 2009 and 2016 there were 35 unrestricted free agents signed to contracts of five years or longer.

What sort of return did teams get on those investments?

Let’s start with this, showing the result of each signing.

[Related: PHT 2019 Free Agent Signing Tracker]

This only includes players that actually changed teams as UFA’s. It does not include re-signings of players still under contract with their current team (contract extensions), or the re-signing of restricted free agents.

• Fourteen of the 35 players were traded before the end of their contract term. That includes nine players that were traded before completing three full seasons with their new team. Most of these trades were salary dumps or an exchange of undesirable contracts.

• Ten of the contracts ended in a buyout, usually after three or four seasons.

• There are only three players signed during this time period that are still playing out their contracts with their current teams: Zach Parise and Ryan Suter in Minnesota, and Michael Frolik with the Calgary Flames. The latter has been mentioned in trade rumors for more than a year now.

• Only four players played out the entire term with the team that signed them: Paul Martin with the Pittsburgh Penguins, Anton Stralman with the Tampa Bay Lightning, Brian Gionta with the Montreal Canadiens, and Dan Hamhuis with the Vancouver Canucks.

• Three players had their careers ended by injury before the duration of the contract: Marian Hossa with the Chicago Blackhawks, Ryane Clowe with the New Jersey Devils, and Mattias Ohlund with the Tampa Bay Lightning.

• On average, those 35 players played out just 57 percent of their contract term with the team that signed them. Fourteen of them played out only half of the contract or less.

• If you want to go with the “I don’t care what happens in six years as long as we win the Stanley Cup with this player” argument, the only players in the above sampling that actually won a Stanley Cup with the team that signed them during their contract were Hossa in Chicago and Matt Niskanen and Brooks Orpik in Washington. The only others to even play in the Stanley Cup Final were Anton Stralman, Valtteri Filpulla, and Matt Carle in Tampa Bay, and Brad Richards with the New York Rangers (he was bought out the following summer after three years of a 10-year contract).

What did teams learn from this sampling?

Mostly nothing, because they have kept doing it.

Between the 2016 and 2018 offseasons there were 13 UFA contracts of five years or more signed, and the early returns are already looking disastrous.

In the summer of 2016 the following deals were signed.

  • David Backes to the Boston Bruins for five years at $6 million per year
  • Kyle Okposo to the Buffalo Sabres for seven years at $6 million per year
  • Frans Nielsen to the Detroit Red Wings for six years at $5.25 million per year
  • Milan Lucic to the Edmonton Oilers for seven years at $6 million per year
  • Loui Eriksson to the Vancouver Canucks for six years at $5.5 million per year
  • James Reimer to the Florida Panthers for five years at $3.4 million per year
  • Andrew Ladd to the New York Islanders for seven years at $5.5 million per year

Not sure there is anybody that would look at any of those contracts just three years later and argue that any of those teams are getting what they hoped to get. Reimer has already been traded so the Panthers could give another long-term deal to a different goalie (Sergei Bobrovsky) this offseason, while the rest of the contracts have all quickly become an albatross for every team that signed them.

There were six contracts signed over the 2017 and 2018 offseasons with Alexander Radulov, Karl Alzner, John Tavares, James van Riemsdyk, Jack Johnson, and John Moore all getting contracts of five years or more.

So far the Radulov and Tavares contracts look to be the best investments and have provided the most return.

Alzner spent time in the AHL this past season, while Johnson has been the subject of trade rumors after just one season in Pittsburgh.

This offseason seven teams have decided to bet against history and take their chances on long-term deals.

  • Vancouver signed Tyler Myers to a five-year contract
  • New York signed Artemi Panarin to a seven-year contract
  • Florida signed Bobrovsky to a seven-year contract
  • Pittsburgh signed Brandon Tanev to a six-year contract
  • Nashville signed Matt Duchene to a seven-year contract
  • New York Islanders re-signed Anders Lee to a seven-year contract

History suggests that probably at least five of these players will be playing for a different team within two or three years.

The players that have had the highest chances of playing out most of their contract are the high-end players (first-or second-line forwards; top-pairing defenders) that are still reasonably close to the prime of their careers, so that might be good news for the Rangers and Panarin and maybe — emphasis maybe — Duchene and the Predators.

All of the rest? These look like textbook deals that are destined to end in a salary dump trade or a buyout within a couple of years.

If a player makes it to unrestricted free agency you should know what you are bidding on and adjust your expectations accordingly. It is usually a player that has almost certainly already played their most productive hockey in the NHL, and it is usually a player that their former team didn’t feel was worth the money or term they were going to be able to get on the open market. It is rare that a team allows a player it actually wants to re-sign and values make it to free agency.

Elite players like Tavares and Panarin are the exception.

The end result is a bidding war for a declining player that probably isn’t as good as you think, which then ultimately leads to a team paying a player to NOT play for them (buyout), or trading them for another player another team doesn’t want, or giving up a more valuable asset to entice a team to take your bad contract in a trade.

NHL Free agency: Sometimes the best way to win is to not play.

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.

Red Wings rebuild won’t be easy, but Yzerman is right GM choice

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Detroit Red Wings fans are right to rejoice. While the move’s been telegraphed for a while, this is indeed a good Friday for the Red Wings, as Steve Yzerman was officially named as their next GM.

Whether it was convincing Steven Stamkos, Nikita Kucherov, and Victor Hedman to sign team-friendly deals, or identifying the league’s general prejudice against smaller players to unearth draft day bargains, Yzerman* did such a great job with the Tampa Bay Lightning, that I’ve called him a magician and/or wizard on multiple occasions.

Even if you’re a vociferous defender of Ken Holland’s latter, sometimes-rebuild-resistant years, chances are, you’re probably very excited about Yzerman’s hiring. The team announced official titles for both Yzerman and Holland, if you like your updates especially granular.

So, to me and plenty others – not just Red Wings fans – this is a shrewd hire.

Still, if there’s one talking point that stands out as especially valid, it’s this: when Yzerman took over the Lightning, he already had an elite center in Steven Stamkos, and a future Norris-winning defenseman in Victor Hedman.

All due respect to Dylan Larkin (who had a strong season, and is only 22) and some other nice players, but the Red Wings don’t have foundational players at quite that superstar level. They do, however, have a pretty interesting setup. If Yzerman is as bright as he seemed to be in Tampa Bay, the Red Wings could really turn things around. All they need is some luck and patience.

Let’s get an idea of the path ahead for Yzerman.

On a Larkin

Look, there’s no shame in Larkin not being quite what Stamkos was in 2010, when Stevie Y took over in Tampa Bay. It’s easy to forget just how potent Stamkos was (the NHL’s most goals [156] and second-most points [283] from 2009-10 to 2010-11), possibly because a few catastrophic injuries briefly derailed his career.

Larkin is fantastic, and stands as the sort of contract you’d build around: a 22-year-old star with a bargain $6.1 million cap hit running through 2022-23.

Anthony Mantha and Tyler Bertuzzi showed great chemistry with Larkin late in the season, with Mantha in particular boasting the sort of pedigree that points to continued success. One of Yzerman’s early challenges will be to strike affordable deals with Mantha, Bertuzzi, and Andreas Athanasiou, three useful forwards whose contracts expire after 2019-20. Would the best deals come in earlier extensions, or would the Red Wings be wiser to wait? It’s up to Yzerman & Co. to decide, and getting good deals could be key if they want to build a winning core.

Early fruits of rebuild

While I’d argue that Holland dragged his feet multiple times when it came to the rebuilding process, the good news is that when Holland did act, he landed some nice building blocks. In trading away Gustav Nyquist, Nick Jensen, and especially Tomas Tatar, the Red Wings have really loaded up on draft picks, most of which land in the top three rounds.

The development processes are already underway for a few interesting prospects, particularly 2018 first-rounders Filip Zadina (sixth overall) and Joe Veleno (30th). The Red Wings once again pick sixth overall in the 2019 NHL Draft, so it’s up to Yzerman to land another blue-chipper, even if Detroit doesn’t get the luxury of a more obvious choice like Jack Hughes or Kappo Kakko.

Almost as important is that the Red Wings have loaded up on picks like they’re at Prospect Costco:

  • Last year, they had those two first-rounders, plus: two second-rounders, and three third-rounders to go with their normal set of choices (minus a fifth-rounder).
  • Via Cap Friendly’s handy chart, the Red Wings have two extra second-round picks and one additional fifth-rounder in 2019.
  • In 2020, they have an extra second and third-round pick. (The third-rounder could turn into a second-rounder depending upon the San Jose Sharks’ actions.)
  • They already have an extra third-rounder in 2021.

That’s a fantastic start, eh? Even the best drafting teams would admit that there’s a lot of “dart throwing” involved in drafting, so it makes sense to load up on those darts, especially when you get the added precision of picks in earlier rounds.

The Lightning were adept at finding quality talent off-the-beaten-path under Yzerman,* most notably identifying Brayden Point as a third-rounder (79th in 2014) and Nikita Kucherov in a second round (58th in 2011). If Yzerman can carry that success over to Detroit, even partially, the Red Wings could really make some exciting leaps.

Cleanup duty

Which brings us to the messier part.

For all of Holland’s accomplishments, he left behind a shaggy salary structure. There’s dead money (Stephen Weiss’ buyout lingers through 2020-21), scary contracts (Frans Nielsen, Justin Abdelkader, Danny DeKeyser), and, erm, maybe too much of a “veteran presence.”

By that I mean this team is old, at least beyond the core. Niklas Kronwall is 38 with a (mercifully) expiring contract, both Jonathan Ericsson and Trevor Daley are 35, and Mike Green is a very banged-up 33. DeKeyser is oft-criticized and not really a spring chicken, either, at 29.

The goalie duo is also creaky. Jimmy Howard was fantastic in 2018-19, but at 35, it’s still surprising that the Red Wings didn’t trade him, even with the understanding that they’d come calling during free agency time in July. Jonathan Bernier is 30 and his $3M cap hit doesn’t expire until after the 2020-21 season.

Most of those trends are disturbing, and while the Red Wings need more talent basically everywhere, the defense and goaltending likely need the most strenuous surgery.

The good news is that a significant chunk of those contracts aren’t lingering too long after Yzerman takes the reins. Kronwall is headed to free agency (or retirement?), while Ericsson, Green, and Daley come off the books after 2019-20. Howard’s extension only lasts through 2019-20, so maybe Yzerman will get trade value out of the veteran where Holland could or would not.

In the short term, and in the case of a few lengthier deals, there’s a significant mess to clean up. The light at the end of the tunnel isn’t too dim, however.

Some pain for future gains

I’ve seen at least mild arguments to try to win now, with at least a portion of The Athletic’s Craig Custance piece (sub required) mentioning certain surprise stories in the NHL. And, sure, if the goal were only to make it back to the playoffs (and maybe even win a series), then speeding up the rebuild would make sense.

My guess is that mega-winner Stevie Y wants his best chance at a Stanley Cup, not merely getting the Red Wings to the playoff bubble.

The free agent market dries up pretty quickly when you realize that Artemi Panarin and Sergei Bobrovsky likely wouldn’t find much of a lure to join a rebuilding team in a cold weather city (heck, “Detroiters” even got canceled).

So, instead of chasing mid-tier free agents and settling for mid-tier expectations, Yzerman should use his clout to absorb another rebuild year or two. Doing so would raise the ceiling on this rebuild, for a few reasons:

  • Most directly and obviously, tanking for an even better pick in 2020. If you look at the teams who regularly contend, virtually all of them required high-end talent found early in drafts.
  • Rather than giving valuable playing time to long-in-the-tooth veterans, why not let younger players learn on the job? You might just get an idea of what you have in, say, Michael Rasmussen. Difference-making players are hitting the NHL earlier and earlier, so why not find out which players can actually make a difference?
  • Allow the Red Wings to be a short-term receptacle to clear cap space, with Detroit taking a bribe, whether that means quality draft picks or useful players. See: the Coyotes landing an important scorer in Vinnie Hinostroza in exchange for keeping Marian Hossa‘s contract warm. Yzerman could even call up his buddies in Tampa Bay and offer to absorb the final year of Ryan Callahan‘s contract ($5.8M cap hit). Boy, Anthony Cirelli and/or Mathieu Joseph would look nice with a winged wheel …
  • Going further, getting more cap space means that the Red Wings could position themselves to land better players in trades than they’d likely entice in free agency. Perhaps teams would ready for the expansion draft by sending good, would-be-exposed players to Detroit for something? Maybe the Hurricanes would sour on Dougie Hamilton, or something similar would happen with P.K. Subban, considering his hefty $9M price tag? Could the Red Wings echo former exec Jim Nill in being the next team to say “Why, yes, we’d love to take Tyler Seguin for 25 cents on the dollar, thank you.”

***

This isn’t an easy job, and again, some of this comes down to luck. Still, it’s easy to see why Red Wings fans are excited.

Make no mistake about it, though: Yzerman has his work cut out for him. It could be the fun sort of work that you’d get from tinkering with a car in the garage, and it should be fascinating for those of us who are dorks when it comes to studying how teams are put together.

* – And his staff, including current GM Julien BriseBois. We could have a lengthy, basically impossible-to-resolve discussion about who was most responsible for the great building in Tampa Bay, but it would be pretty fruitless. And, really, wouldn’t all smart GMs want to surround themselves with other smart people?

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.

WATCH LIVE: Flyers host Jets on NBCSN

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NBCSN’s coverage of the 2018-19 NHL season continues with Monday’s matchup between the Winnipeg Jets and Philadelphia Flyers. Coverage begins at 6 p.m. ET on NBCSN. You can watch the game online and on the NBC Sports app by clicking here.

While the Tampa Bay Lightning lead the NHL with 76 points, the Western Conference has a tighter race at the top, especially in the Central Division, where Winnipeg currently owns the top spot and has four games in hand on the second-place Nashville Predators.

The Jets are currently on pace for 109 points and 52 wins. Last season, the team set franchise records in both wins (52) and points (114), but they still didn’t win the division (Nashville did w/ NHL-best 117 pts).

All-Stars Blake Wheeler and Mark Scheifele are top two on the team in points at 61 and 59, respectively. Kyle Connor is next with 38. Wheeler, tied for ninth in the NHL in points, is second in the league in assists (52) and although his streak of 20-goal seasons may end at five given he has only nine goals, he’s on pace for 104 points, which would be a career high and break Marian Hossa’s franchise record of 100.

In addition to the All-Star break, both teams are coming off their bye weeks, each having last played on Saturday, Jan. 19.

One of the bottom-dwellers of the Eastern Conference, the Flyers sit 14 points back of a playoff spot and are on track to continue their trend of missing the postseason the year after making it. From 1995-2012, the Flyers made the playoffs 16 times in a 17-season span. Since then, Philly has made just three postseasons in the last six years and each in alternating years.

Wayne Simmonds, a popular name in trade talks ahead of the Feb. 25 deadline, has played in all 48 games this season and put up 15 goals but just 23 points. He’s on track for his sixth straight season with 24-plus goals but only 39 points, which would be his fewest in a full season since 2011.

The Flyers are 7-8-2 since interim coach Scott Gordon took over for Dave Hakstol. The coaching change was one of several moves in what has been a tumultuous season for the team that has also included letting go of GM Ron Hextall and replacing him with Chuck Fletcher.

[WATCH LIVE – COVERAGE BEGINS AT 6 P.M. ET – NBCSN]

What: Winnipeg Jets at Philadelphia Flyers
Where: Wells Fargo Center
When: Monday, Jan. 28, 6 p.m. ET
TV: NBCSN
Live stream: You can watch the Jets-Flyers stream on NBC Sports’ live stream page and the NBC Sports app.

PROJECTED LINEUPS

JETS
Kyle Connor – Mark Scheifele – Blake Wheeler
Patrik LaineBryan LittleJack Roslovic
Mathieu PerreaultAdam LowryBrandon Tanev
Brendan LemieuxAndrew CoppMason Appleton

Josh MorrisseyJacob Trouba
Dmitry KulikovTyler Myers
Joe Morrow – Sami Niku

Starting goalie: Connor Hellebuyck

FLYERS
James van RiemsdykClaude GirouxTravis Konecny
Oskar LindblomSean CouturierJakub Voracek
Scott LaughtonNolan Patrick – Wayne Simmonds
Phil Varone – Mikhail Vorobyev – Michael Raffl

Ivan ProvorovTravis Sanheim
Shayne GostisbehereAndrew MacDonald
Robert HaggRadko Gudas

Starting goalie: Carter Hart

Kenny Albert and Brian Boucher will have the call from Wells Fargo Center in Philadelphia, Pa. Pre-game coverage starts at 6 p.m. ET with NHL Live, hosted by Paul Burmeister alongside Jeremy Roenick and Anson Carter.

Blackhawks should try to trade star defensemen

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The Athletic’s Scott Powers dropped an interesting report today (sub required): Chicago Blackhawks GM Stan Bowman realizes that he’ll have a glut of defensemen soon, so he might need to make a move.

To be more specific, the impending return of Connor Murphy could make for quite a crowd. Powers notes that Bowman acknowledged that much a couple weeks ago, albeit while also resisting some of the perceived pressure to make a move.

” … Murph’s a good player, so we want to get him back as soon as we can to help our team. What that means for the other guys, we’ll sort that out,” Bowman said on Nov. 24. “If there’s a surplus and everyone’s healthy, then there’s always needs around the league for defensemen. We can maybe make a move at that point.”

Now, Powers points to Bowman trying to move a depth defenseman such as Brandon Manning or Jan Rutta merely to open up a modicum of space … but that honestly might be thinking too small.

Right now, the Chicago Blackhawks are on a six-game losing streak. They’re not technically in last place in the West with 23 points, yet they’re sagging with 30 games played already, so they’re awfully close to that mark. Maybe playing five of their next six games at home will help them save a little face, but just about every projection should hammer a painful reality home: the 2018-19 season is as good as shot for Chicago.

With that in mind, the Blackhawks should begin preparing for the future, and that means acknowledging – not continuing to ignore – the elephant in the room: it’s time to strip away significant portions of this core group.

It’s tough to imagine the Blackhawks parting ways with the $21 million duo of Jonathan Toews and Patrick Kane, and in all honesty, those two could still conceivably help a team contend.

Instead, it’s time for Bowman to hit the “reset” button on an ailing defense, and he’d be foolish not to explore every avenue in doing so. Yes, that means doing whatever he can to a) convince Duncan Keith and Brent Seabrook to waive no-movement clauses and b) finding trade partners for one or both of those defensemen.

The risks that come with keeping Keith

At 35, Keith isn’t at that Norris Trophy level any longer.

Defensemen aren’t always sniping machines, yet it’s troubling that he’s failed to score a goal in 2018-19, and only has two over his last 112 games. He’s not quite the source of offense he once was, and while his possession stats are respectable, they won’t knock your socks off.

Keith is still a very useful defenseman, however, and one can bet that he still enjoys a high standing in the NHL … for now.

Let’s face it; as times go on and Keith’s team declines further from past successes, his stature is likely to tumble. It doesn’t help that his average ice time is down considerably this season (22:36), and last season’s 23:50 TOI average was already a significant step down from his workhorse, 25+ minute days.

The Blackhawks need to be weary of Keith’s $5.54M cap hit, which lasts through 2022-23. Yes, it carries the scent of obvious cap circumvention, as Cap Friendly lists his salary diving from $4.5M to $3.5M next, and so on until it sinks all the way to $1.5M in 2022-23. In my opinion, Chicago would get a much better return for Keith if they traded him before he became, essentially, Marian Hossa-like contract fodder.

(Sure, the Blackhawks moved Hossa’s deal, but they had to give up a helpful, affordable, and not-yet-optimized player in Vinnie Hinostroza.)

If the Blackhawks wait too long, they might be stuck bribing a team to take the last, empty cap years of Keith’s deal, rather than getting assets that can truly help them in the future. That’s not exactly an ideal scenario for a franchise that sorely needs to restock its prospect cupboard beyond Adam Boqvist.

Finding a taker for Brent Seabrook

While Keith could conceivably fetch an interesting offer, it’s difficult to picture GMs lining up to land Seabrook, a 33-year-old with a horrendous $6.875M cap hit that doesn’t expire until after 2023-24.

On the other hand, we’ve seen some surprising trades over the years that force you to never say never.

The Habs didn’t just absorb a nightmare Scott Gomez contract, they also sent Ryan McDonagh to the Rangers. A contract Roberto Luongo despised didn’t keep him in Vancouver forever. Chris Pronger eventually drew checks from the Coyotes.

Seabrook will be easier to move in time, as his total salary goes from $9M in the first three seasons (ending in 2018-19) to $7.5M next year, and lower as the years pass. That’s a comforting thought, but are we totally certain that Bowman has been practicing due diligence to get rid of that deal as soon as possible? You never know if an old-school team might want to take Seabrook off of Chicago’s hands sooner.

All it takes is one GM/front office to think that they’re seeing something no one else understands. Unfortunately, it’s fair to wonder if Bowman is too close to the situation, and thus overrates his own players to his own detriment.

One to keep

If there’s one defenseman I wouldn’t take many trade calls about, it would be rookie Henri Jokiharju. The 19-year-old is already showing serious promise, and maybe just as importantly for the cap-challenged Blackhawks, he’s only in the first season of his three-year, entry-level, rookie deal.

Which brings us to some optimism:

If they can only stomach a short rebuild …

Normally, I’d refer to this idea as a “soft rebuild,” but let’s be frank: it won’t be easy for Bowman to swallow his pride and, ideally, trade Keith and/or Seabrook. Management probably wouldn’t even enjoy moving a more obvious cap-filler like forward Artem Anisimov.

Could there be some light at the end of the tunnel, though?

It certainly stings that Chicago lost some quality, affordable players in recent years because of the cap crunch and some general errors (Hinostroza, Ryan Hartman, Teuvo Teravainen, Nick Schmaltz, etc.).

They still might have some help thanks to certain cheaper options. As mentioned, Jokiharju could be part of a solution. Rising star Alex DeBrincat‘s rookie contract won’t expire until after next season. If Dylan Strome can at least bring more pros than cons, then he’s another guy who is cheap through at least 2019-20. Depending upon how he develops, Boqvist might be able to add to that group of cheap, competitive players.

According to Cap Friendly, the Blackhawks currently have 15 players carrying $62.21M in cap commitments heading into 2019-20. If Chicago moved Keith or Seabrook for futures and/or expiring contracts, they could push that number closer to $56M or so (considering overages and other cap quirks).

Suddenly, things could look more interesting with a salary cap estimated around $83M.

Perhaps the Blackhawks could right a wrong by bringing back Artemi Panarin, giving them more of a chance to outscore their problems? Maybe they could lure Erik Karlsson away from San Jose and other suitors? They could also target mid-level free agents in pursuit of depth, or extend their rebuild window by taking on some contracts from other teams (maybe they should “help out” the Maple Leafs?).

Things can start to change quickly once you gain some flexibility, with some ideas being wiser than others. Most of the bolder ideas sure beat sitting idly by, risking waiting too long to make much-needed changes.

For the sake of Blackhawks fans, here’s hoping Bowman agrees, even if it means painfully saying goodbye to some of the icons of a fading era.

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.

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.

***

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.