Patrick Marleau

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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.

Examining the Ducks’ options with Corey Perry

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One way or another it appears as if Corey Perry‘s time with the Anaheim Ducks is coming to a close over the next few weeks. Over the weekend the Athletic’s Pierre LeBrun and Eric Stephens both reported extensively on the team’s willingness to move on from their long-time star winger and former league MVP in an effort to get younger.

It should be pretty obvious as to why the Ducks are looking to move on and make a change. The franchise as currently constructed has hit its ceiling with its current core, while Perry carries a substantial salary cap hit (more than $8.6 million per season over the next two seasons) for what has been steadily declining production over the past three seasons.

LeBrun reported that if the Ducks fail to find a taker in a trade they would consider buying him out during the league’s buyout window later this month. According to the buyout calculator over at Capfriendly, a buyout of Perry’s remaining contract would leave the Ducks on the hook for a $2 million salary cap hit in 2019-20, 2021-22 and 2022-23, with a $6 million cap hit in 2020-21. That would be a pretty drastic step to take with a franchise icon, but the Ducks aren’t currently getting $8.6 million worth of production out of Perry and it seems unlikely that he is ever going to return to that level.

He was limited to just 31 games this past season where he scored six goals and four assists. That came after a 2017-18 season where he managed 17 goals and 49 total points in 71 games, which came after a 19-goal, 53 point season the year before. For three years now his production has been cratering across the board, whether it’s his traditional box score numbers (goals, assists, points) or his underlying numbers that look at his possession and shot numbers. It is not just that he’s lost some of his fastball when it comes to his shot and ability to beat goalies, but he is also not able to generate anywhere near as many shots as he did when he was a consistent 35-40 goal scorer and one of the league’s elite power forwards.

To get a sense for just how far — and how quickly — his game has fallen off, just consider that since the start of the 2016-17 season he has the following league-wide ranks among forwards that have played at least 100 games (rankings are out of 405 forwards):

Goals per game: 147th
Points per game: 122nd
Shots per game: 87th
Even-strength goals: 188th
Corsi Percentage: 273rd

Compare that to where he was in the three years prior to that:

Goals per game: 4th
Points per game: 16th
Shots per game: 28th
Even-strength goals: 1st (tied with Alex Ovechkin)
Corsi Percentage: 126th

That is significant.

So, yeah, it is understandable as to why the Ducks would be looking to move on.

The Ducks have a significant chunk of money tied up in an aging core (including Perry, Ryan Getzlaf, and Ryan Kesler, whose career seems to be in serious jeopardy) that saw its run of six consecutive playoff appearances end this past season. Even though the franchise is just two years removed from a trip to the Western Conference Finals the team has rapidly declined over the past two seasons and looks to be several steps below the rest of the Stanley Cup contenders in the Western Conference. They looked overwhelmed in their 2017-18 Round 1 sweep at the hands of the San Jose Sharks, and despite getting an All-Star worthy performance from starting goalie John Gibson this past season the team was never really even close to being competitive. The potential for major changes existed even before the start of the season, and given how badly things went once the season began it is clear the time has come to turn the page.

For as great as Perry has been for the team during career, he is at this moment a natural starting point for those changes given the total package he provides (age, contract, production).

The problem is the Ducks probably do not have many good options when it comes to moving on.

Keeping him is not really ideal because they would still paying superstar money for a player that, when healthy, is probably giving them second-line (at best) production. For a team that is looking to get younger and does not always spend to the salary cap that is a tough contract to justify, especially when it is likely that the production is only going to keep declining over the next two years.

Even with that being said, buying him out should be an absolute last resort because even though there are some cap savings that come with that, they are still going to be on the hook for a significant portion of money over the next four years while getting nothing in return for it. And it is not like Perry is a zero value player. Somebody else could use him as he can still play and produce a little bit. It just not at an $8.6 million dollar level. That salary cap number is probably double what he would get on the open market right now as a free agent.

That leaves the trade market, which probably will not be easy or result in a satisfying return for Ducks fans (or Perry’s current Ducks teammates).

Given the size of his salary the next two years and the decline he is experiencing it might have the look of an unmovable contract, but there is really no such thing in the NHL. Every contract can be moved, you just have to find the right team that is willing to work with you. If the Ducks do find a trade partner the framework of a deal is probably going to look like another trade involving a similarly aging player where they either have to retain a significant portion of salary, and/or take on another team’s bad contract in return.

It is the same situation the Edmonton Oilers find themselves in with Milan Lucic and the same situation the Toronto Maple Leafs find themselves in with Patrick Marleau. It is the same situation the Los Angeles Kings found themselves in with Marian Gaborik a couple of years ago and the Ottawa Senators with Dion Phaneuf (who were eventually swapped for one another, while the Kings will ultimately find themselves in the same situation now that they have Phaneuf).

The problem with that option is it still leaves them in a situation where they are probably overpaying a declining player under the cap, which then forces them to ask the question: Why even make the trade? In that case it would depend on what else they can get in return. Perry would still probably be better and more valuable than whatever player the Ducks take on in return, which should result in additional assets thrown their way (a younger player, a decent draft pick, etc.).

The other option in a trade: Retain a significant chunk of salary over the next two years. They are still paying something under the cap for a player that isn’t playing for them, but if the Ducks are willing to eat some of that money it should — should being the key word — result in a better return. Perry may not have much value to another team at $8.6 million per season, but he might have some value at, hypothetically speaking, $5 or 6 million. It is cheaper long-term than a buyout, and it gives them something tangible in return to add to the organization.

None of this is an ideal way for the Ducks to part ways with a player that helped the team win a Stanley Cup, won an MVP award, and is one of the franchise’s all-time greats. It is simply the reality of playing in a salary cap league and spending significant money on players well beyond their 30th birthdays.

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.

 

PHT Morning Skate: Takeaways from combine; Boring Marchand

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Welcome to the PHT Morning Skate, a collection of links from around the hockey world. Have a link you want to submit? Email us at phtblog@nbcsports.com.

• A lot went wrong for the Anaheim Ducks in 2018-19, but Rotoworld.com’s Ryan Dadoun dug a little deeper. (Rotoworld)

• There’s just not slowing down Tuukka Rask in the 2019 Stanley Cup Playoffs. (The Hockey News)

• Here are 10 takeaways from the 2019 NHL Draft Combine. (Sportsnet)

• A specific moment in Game 3 showed another problem with offside reviews the NHL will have to look at. (Stanley Cup of Chowder)

• Has Brad Marchand become boring? (WEEI)

Marcus Johansson‘s price tag on his next contract just keeps on climbing. (NBC Sports Washington)

• Should the Flyers submit an offer sheet to restricted free agent Matthew Tkachuk? (Broad Street Hockey)

• Why aren’t the Lightning in the Stanley Cup Final? Here are five reasons. (Tampa Bay Times)

• Now that Nikita Zaitsev wants out of Toronto, what does that mean for the rest of the group? (Toronto Star)

• Find out why draft history isn’t on the side of Jack Hughes or the New Jersey Devils. (New York Post)

• It’s been a long time since the St. Louis Blues have hosted a game in the Stanley Cup Final. A lot has happened since then. (St. Louis Game-Time)

David Perron deserves to be made a healthy scratch, per Bleedin’ Blue blog. (Bleedin’ Blue)

• Craig Berube doesn’t agree with a lot of the calls made against his team in the Stanley Cup Final. (ESPN)

• Tuukka Rask has had some goofy interviews with Finnish media. (Sportsnet)

• The perfection line kicked into gear for the Bruins in Game 3 of the Stanley Cup Final. (NBC Sports Boston)

• The NHL Draft really starts when the Los Angeles Kings pick at no. 5. (The Score)

• Rick Bowness could be an intriguing option to be the next head coach for the Anaheim Ducks. (Anaheim Calling)

• The Maple Leafs and Kings have reportedly discussed a trade involving Patrick Marleau. (Leafs Nation)

• Here’s how a Punjabi hockey announcer is changing hockey. (Deadspin)

• The chance to be with a hockey team day-to-day was too much of a thrill for Dave Tippett to pass up. (Seattle Times)

• After leaving the Buffalo Sabres in December, Patrik Berglund says he’ll play hockey next year. (Yahoo)

Joey Alfieri is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @joeyalfieri.

Why rebuilding teams should trade for players like Marleau

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The Athletic’s Pierre LeBrun, Sportsnet’s Nick Kypreos, and others have discussed an intriguing possibility that the Los Angeles Kings might trade for Patrick Marleau from the cap-strapped Toronto Maple Leafs.

On its face, that seems like an ill-advised trade. Why would the already-old-as-dirt, expensive Kings seek out a near-40-year-old who carries a bloated $6.25 million cap hit?

Yet, in the cap era, it’s a deal that could make a ton of sense for both sides, if the right deal could be hashed out.

The Kings should go even bolder

While LeBrun discusses the Kings wanting to get rid of a different, cheaper problem contract to make the Marleau trade work (sub required), the real goal should be for both teams to acknowledge their situations. The Maple Leafs needs cap space; the Kings need to build up their farm system with picks and prospects.

Instead of trying to move, say, Dustin Brown or Ilya Kovalchuk, the Kings should instead find as creative ways as possible to bulk up on futures, while accepting the (admittedly grim) reality that they’ll suffer through 2019-20, if not 2020-21 and beyond.

In fact, if I were Kings GM Rob Blake, I’d pitch sending over Alec Martinez for Marleau, with the goal of really making it costly for the Maple Leafs. Imagine how appealing it would be for the Maple Leafs to move out Marleau’s contract and improve their defense, and imagine how much more of a ransom the Kings could demand if they’re absorbing all the immediate “losses” in such a trade? Could Los Angeles land yet another Maple Leafs first-rounder, say in 2020 or even 2021? Could such a deal be sweetened with, say, the rights to Andreas Johansson?

That trade might not work, but it’s a blueprint

The Los Angeles Times’ Helene Elliott believes that a deal probably won’t actually work out, and that’s understandable. There are a lot of ins and outs to a would-be trade that could send Marleau to L.A., particularly since Marleau would need to waive his no-trade clause to complete a trade.

But, really, this is just one example.

Rebuilding teams should apply similar logic to any number of other situations, while contenders can be forgiven for thinking more short-term.

Of course, a rebuilding team would also need to embrace the rebuilding reality, and not every team is past the denial stage.

Potential rebuilding teams

The Kings are in a decent position to absorb a tough year or two, what with being not that far removed from two Stanley Cup wins. The Ottawa Senators have already prepared fans for a rebuild, although they also need to avoid making things too brutal after an agonizing year. The Detroit Red Wings could be less resistant to rebuilding under Steve Yzerman than Ken Holland. Other teams should probably at least consider a short pulling off of the Band-Aid, too, with the Anaheim Ducks coming to mind.

What are some of the problem contracts that could be moved? Glad you (may have) asked.

Also, quick note: these mentions are based on my perception of the relative value of players, not necessarily how their teams view them.

Marleau-likes (challenging contracts ending after 2019-20)

  • Again, Marleau is about to turn 40, and his cap hit is $6.25M. His actual salary is just $4.25M, with Cap Friendly listing his salary bonus at $3M. Maybe the Maple Leafs could make his contract even more enticing to move if they eat the salary bonus, then trade him? If it’s not the Kings, someone should try hard to get Marleau, assuming he’d waive for at least a few situations.
  • Ryan Callahan: 34, $5.8M cap hit, $4.7M salary. Callahan to the Red Wings almost feels too obvious, as Yzerman can do his old team the Lightning a cap-related favor, get one of his beloved former Rangers, and land some much-needed pieces. Naturally, other rebuilders should seek this deal out, too, as the Bolts are in just as tough a spot with Brayden Point as the Maple Leafs are in trying to sign Mitch Marner.
  • Nathan Horton: 35, $5.3M cap hit, $3.6M salary. The Maple Leafs have been placing Horton on LTIR since acquiring his contract, but with his reduced actual salary, maybe a team would take that minor headache off of Toronto’s hands?
  • David Clarkson: 36, $5.25M cap hit, $3.25M salary. Basically Vegas’ version of the Horton situation.
  • Zach Bogosian: 29, $5.14M cap hit, $6M salary. Buffalo’s said the right things about liking Bogosian over the years, but with big spending coming up if they want to re-sign Jeff Skinner, not to mention get better … wouldn’t they be better served spending that money on someone who might move the needle?
  • Andrew MacDonald: 33, $5M cap hit, $5.75M salary. Like Bogosian, MacDonald’s salary actually exceeds his cap hit. Maybe you’d get a better return from Philly if you ate one year of his deal? Both the Flyers and Sabres have some added urgency to be better in 2019-20, after all.
  • Martin Hanzal: 33, $4.75M cap hit, $4M salary. The Stars already have a ton of cap space opening up while they made big strides during the 2019 Stanley Cup Playoffs. You’d think they’d be eager to get more room, earlier, and maybe make a run at someone bold like Artemi Panarin or Erik Karlsson? They were one of the top bidders for Karlsson last summer, apparently, but now they could conceivably add Karlsson without trading away a gem like Miro Heiskanen.
  • Dmitry Kulikov: 29, $4.33M cap hit and salary. Maybe the Jets could more easily keep Jacob Trouba along with Patrik Laine and Kyle Connor if they get rid of an underwhelming, expensive defenseman? Just a thought.

If you want to dig even deeper, Cap Friendly’s list is a great guide.

Two years left

Seeking contracts that expire after 2020-21 is a tougher sell, but maybe the rewards would be worth the risk of extended suffering?

  • Corey Perry: 36, $8.625M cap hit. $8M salary in 2019-20; $7M salary ($4M base; $3M salary bonus) in 2020-21. If you’re offering to take on Perry’s contract, you’d probably want a significant package in return. If the Ducks are in rebuild denial, then they’d get a fresher start if they managed to bribe someone to take Perry. Ryan Getzlaf‘s deal also expires after 2020-21 with similar parameters, though it’s less appealing to move him.
  • Kevin Shattenkirk: 32, $6.65 cap hit, cheaper salary in 2020-21. Marc Staal, 34, $5.7M cap hit, cheaper salary in 2020-21. The Rangers’ future is blurry now, as they could go from rebuild to trying to contender if they get Panarin. If they’re really gearing toward contending, maybe they’d want to get rid of some expensive, aging defensemen?
  • David Backes: 35, $6M cap hit, $4M salary each of the next two seasons. The bottom line is that Backes has been a pretty frequent healthy scratch, and the Bruins should funnel his cap hit toward trying to keep both Charlie McAvoy (RFA this offseason) and Torey Krug (UFA after 2020-21).
  • Alexander Steen: 37, $5.75M cap hit, cheaper in 2020-21. Paying this much for a guy who’s become a fourth-liner just isn’t tenable for a contender. He’s been great for the Blues over the years, yet if you want to stay in the mix, you sometimes need to have those tough conversations.
  • Lightning round: Brandon Dubinsky, Matt Niskanen, Artem Anisimov, and Jake Allen, among others. There are a lot of other, less-obvious “let’s take this off your hands” considerations. Check out Cap Friendly’s list if you want to dive down that rabbit hole.

***

As you can see, plenty of contenders have contracts they should try to get rid of, and rebuilding teams should capitalize on these situations.

Interestingly, there are fascinating ideas if rebuilders would take on even more than a year or two of baggage. Would it be worth it to ask for a lot for, say, James Neal, particularly if they think Neal might be at least a little better than his disastrous 2018-19 season indicated? Might someone extract a robust package while accepting Milan Lucic‘s positively odious contract?

It’s easier to sell the one or two-year commitments, which is why this post focuses on those more feasible scenarios. Nonetheless, it would be fun for the armchair GMs among us to see executives get truly creative.

Should your team seek these trades out? What level of risk is too much to stomach? Do tell in the comments.

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.

Leafs have big decisions to make this summer

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Another year, another first-round exit for the Toronto Maple Leafs in the Stanley Cup Playoffs. Since 2013, the Leafs have been knocked out by the Boston Bruins in Game 7 of the first round three times. Last year, Toronto had a 3-2 lead against Boston in the deciding game, but they let it slip away. So what did they do? They added John Tavares in free agency and Jake Muzzin before the trade deadline. Still, it wasn’t enough.

So now what?

General manager Kyle Dubas will have his work cut out for him this summer. The Leafs have three key players scheduled to become restricted free agents in Mitch Marner, Kasperi Kapanen and Andreas Johnsson. They also have two important blueliners set to hit the open market in Jake Gardiner and Ron Hainsey.

Let’s start with the defense because we know that’s where the Leafs need the most work.

Leafs fans like to pin blame on Gardiner because he tends to make silly decisions with the puck at times, but nobody can deny that their defense is better with him than without him. The 28-year-old was clearly banged up in the playoffs, and that definitely affected his play. You’d have to think that his services will be in high demand on July 1st because there won’t be too many puck-moving defenders available this summer.

As for Hainsey, he played over 20 minutes per game in the regular season and playoffs. But how much longer can the Leafs continue rolling out a 38-year-old player on their top pairing? They need to upgrade on defense, which means Hainsey doesn’t come back or he gets pushed further down the lineup.

Dubas already has $75.759 million committed to the cap next season, which means that he’ll likely have less than $8 million in cap space. Marner alone will command way more than $8 million per season, so the Leafs will have to get creative when it comes to opening up dollars to re-sign players and to bring in new bodies.

Both Johnsson and Kapanen scored 20 goals and both surpassed the 40-point mark this season, but Johnsson (43 points) averaged under 14 minutes per game, while Kapanen (44 points) played over 16:30 per game. Could one of those two guys be on the move? Will it be Kapanen?

But the five players with expiring contracts mentioned above aren’t part of that $75-plus million cap hit heading into next season. Players under contract will have to move, too. 39-year-old Patrick Marleau is on the books for $6.25 million for one more year and he clearly isn’t the same player he once was. Can they find a taker for him? Dubas might have to send Kapanen to a team that’s willing to eat Marleau’s contract.

Nazem Kadri has three years left on his current contract at a very reasonable cap hit of $4.5 million. There’s no denying that his five-game suspension against the Bruins effected the outcome of the series. Has he worn out his welcome in Toronto? He’s still an effective player, but the trust between he and the organization may be fractured at this point.

Nikita Zaitsev‘s contract ($4.5 million AAV per year) forces him into a top four role that he probably isn’t suited for over an 82-game season plus playoffs. Other teams won’t be lining up to trade for that contract.

Dubas was the big winner last offseason, as he found a way to bring Tavares home. He also made a solid trade with Los Angeles for Muzzin and he was able to get Auston Matthews to sign a long-term extension, but this is the first major challenge he’ll experience as GM of the Leafs.

How will he respond?

MORE:
In a series full of questions, Mike Babcock short on answers
Bruins win yet another Game 7 versus Maple Leafs

Joey Alfieri is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @joeyalfieri.