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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.

Trade: Flames get Lucic; Oilers receive Neal

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Call it a “change of scenery,” or probably most directly, trading problems. Either way, Alberta rivals the Calgary Flames and Edmonton Oilers made a truly resounding trade on Friday, with the main takeaway being that Milan Lucic goes to the Flames, while James Neal is bound for Edmonton.

Yeah, wow.

Multiple reporters indicate that it’s close to one-for-one, although there are a few minor tweaks to consider.

The Calgary Herald’s Kristen Anderson reports that the Oilers are retaining 12.5 percent of Milan Lucic’s salary, which translates to $750K, while Edmonton is also sending Calgary a conditional third-round pick in 2020. It’s not clear yet what those conditions are.

If Anderson and others are correct, that means the trade boils down to:

Flames receive: Lucic, 31, minus $750K per year. That puts Lucic at $5.25M, with his contract running through 2022-23. Calgary also receives Edmonton’s 2020 third-round pick, if conditions are met.

Oilers receive: Neal, 31, who has a $5.75M cap hit that runs through 2022-23.

As you can see, the two players remain very similar in both cap hit, term, and even age. The Flames save $500K in cap space, while the Oilers add $500K, as Puck Pedia confirms.

Of course, when you’re talking about contracts teams largely want to get away from, it’s often about more than just cap hits. There are some significant ins and outs to that side of the discussion, including Lucic’s deal being essentially “buyout proof.” Neal, meanwhile, would be easier for the Oilers to buy out, if they decide to do that after an audition with the team.

On Saturday, PHT will try to wade through the variety of paths the two teams could take, whether it means sticking with Lucic and Neal respectively, or going for a buyout or trade. For now, let’s consider where they are in their careers.

Lucic’s tough times

After a productive first season in Edmonton where Lucic scored 23 goals and 50 points in 2016-17, Lucic plummeted down the depth chart and in production. This past season was rock bottom, as Lucic scored just six goals and 20 points in 79 games.

The bet on Lucic, some might say in part leading to the dreadful Taylor Hall trade, stands as one of the landmark gaffes of Peter Chiarelli’s Era of Error in Edmonton. It was clear that both the player and team needed to part ways, so now there’s at least peace in that regard.

A bumpy path for Neal, and brutal times in Calgary

Whether you like Neal – a player who absolutely goes over the line at times, when he loses his cool – or not, it’s tough not to feel for him after the last several years.

He was traded from the Stars to the Penguins in 2011, scapegoated a bit out of Pittsburgh on his way to Nashville in 2014, then scooped up by Vegas in the 2017 expansion draft, only to sign with the Flames (possibly in a relatively lukewarm free agent market) last summer. Now this trade sends Neal to Edmonton, making this the 31-year-old’s sixth NHL team, and his fourth in his past four seasons. Players as productive as Neal – aside from last season’s meltdown – rarely become journeymen like this.

Honestly, should we just get his nameplate ready for the Seattle [Unfortunately Not Supersonics] right now?

Despite that upheaval, Neal had been a guy who could score goals nonetheless. He peaked with 40 during his best days with Malkin in Pittsburgh (an 81-point output in 2011-12), but he sniped in multiple climates, generating 20+ goals in 10 consecutive seasons.

And then this Calgary season happened.

Neal never clicked with Johnny Gaudreau and Sean Monahan, as Elias Lindholm instead took that plum gig. Neal slipped lower and lower in the lineup, sometimes becoming a healthy scratch, and ended 2018-19 with Lucic-like numbers (though in fewer games), as Neal managed only seven goals and 19 points. He was also an all-around disaster, as you can see from RAPM charts via Evolving Hockey that argue that, in some ways, Lucic was actually better last season, as Lucic at least wasn’t as much of a defensive disaster as Neal. Faint praise, but still:

Better times ahead, maybe?

Again, it’s easy to forget that both wingers are 31.

That’s not a great age to be when your contract looks inflated, but there’s also a chance that maybe both could turn things around, at least to some degree. With Neal closer to more productive seasons than Lucic, he’d seem to be a more likely candidate, especially if his rifle of a shot pairs nicely with Connor McDavid‘s all-world playmaking.

But both players have a shot at positive regression. Neal’s five percent shooting percentage from 2018-19 marked the only time in his career that he’s been below 10.4 percent, while Lucic shot at 6.8 in 2017-18 and 8.1 in 2018-19, compared to his career average of 13.5 percent.

Modest rebounds wouldn’t guarantee that either Neal or Lucic sticks around in their new climates. Improvements might just make each forward easier to trade, and more palatable to keep around while looking for trades. There’s simply a lot of room for “to be continued” elements to this move, from buyouts to trades and more.

***

As discussed above, there could still be twists and turns in these sagas, and some of those possibilities will be examined on Saturday. Yet, at this moment in time, this seems like the rare trade win for the Oilers. Maybe this is the start of a positive pattern now that Ken Holland is GM?

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.

Trouba gets seven-year, $56 million deal from Rangers

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The New York Rangers have locked up Jacob Trouba with a seven-year, $56 million contract.

Trouba saw his restricted free agent rights acquired by the Rangers last month from the Winnipeg Jets in exchange for defenseman Neal Pionk and 2019 first-round pick (Ville Heinola). General manager Jeff Gorton added up front by bringing Artemi Panarin to Broadway on July 1, so you knew that they were going to eventually come to an agreement to keep the 25-year-old defenseman in the fold following the June trade as they bulk up for a run in 2019-20.

“They’re building a winner tends to be the vibe I’ve gotten,” said Trouba following the trade to New York. “They treat the players first class. It’s very first-class organization. I mean, it’s New York so you’ve got a big stage and they expect a lot out of their team. We want to ultimately get to the Stanley Cup.”

 

Earlier this month Trouba had elected salary arbitration and had a July 25 date scheduled. But that was merely a formality to allow extra time for both sides to hammer out a deal.

According to PuckPedia, $22 million will be paid to Trouba over the next three seasons via signing bonuses and he has a no-move clause from 2020-21 to 2023-24 and a limited no-trade clause in the final two years of the deal.

[ProHockeyTalk’s 2019 NHL free agency tracker]

The ninth overall pick in the 2012 NHL Draft, Trouba has spent the last six seasons with the Jets, playing 408 games and recording 42 goals and 179 points. In 2018-19 he set a career high with 50 points, making him the ninth defenseman 25 or younger to hit that mark in the past three seasons.

Gorton still has work to do this summer in deciding whether to re-sign RFAs Pavel Buchnevich (July 29 arbitration hearing), Brendan Lemieux and Tony DeAngelo, while working around the salary cap, which after this signing puts them over the ceiling. This could end up leading to a trade of Chris Kreider, who’s entering the final year of this deal carrying a $4.625 million cap hit but owed $4 million in salary for the coming season. They also have a 48-hour buyout window later this summer as well even if they settle with Buchnevich before his hearing.

MORE: Jets were never going to get enough for Trouba

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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.

Key defensemen enter contract years, possible free agency

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Despite being the most exciting offseason since PHT started in 2010, the NHL will probably always lag behind the NBA when it comes to stars moving in free agency.

Rudely, players like Sidney Crosby and Connor McDavid don’t even flirt with drama, instead sticking with their teams by signing extensions, often almost at the first possible moment they legally can. Again, rude.

So, it’s important to get that disclaimer out of the way. Chances are, the fascinatingly robust list of pending free agent defensemen will narrow down, possibly starting before the 2019-20 season begins.

But, even so, it’s quite the list, and a lot of these defensemen will earn enormous, team-changing raises, whenever their next deals get signed.

And, hey, sticking with your team can still alter its course. Just look at how scary that Drew Doughty extension ($11 million AAV through 2026-27) seems today compared to when Doughty re-upped with the Kings in July 2018.

Let’s consider some of the most intriguing names, split by UFA and RFA designations. Cap Friendly’s listings were helpful in putting this together, and being that these lists aren’t comprehensive, you may enjoy digging deeper there to find even more.

Prominent UFAs

Alex Pietrangelo (Blues), Roman Josi (Predators), Tyson Barrie (Maple Leafs), Torey Krug (Bruins), Jared Spurgeon (Wild, more on them here), Justin Faulk (Hurricanes), Jake Muzzin (Maple Leafs), Justin Schultz (Penguins), Christopher Tanev (Canucks), T.J. Brodie (Flames), Sami Vatanen (Devils), Travis Hamonic (Flames).

The headliners of this list – particularly Pietrangelo and Josi – must have licked their chops when Erik Karlsson signed that mammoth eight year, $92M ($11.5M AAV) contract with the Sharks. Pietrangelo and Josi don’t boast multiple Norris Trophies, yet they might also be healthier than Karlsson when he signed his deal, so there could be interesting value debates.

Either way, Roman Josi’s borderline-insulting $4M won’t cut it after 2019-20.

The marquee names are the most intriguing, yet there are interesting situations as you go down a rung and more. And those are the players who are arguably more likely to sign with new teams.

[ProHockeyTalk’s 2019 NHL free agency tracker]

Would Toronto be able to bring back even one of Barrie or Muzzin after next season? Are the Hurricanes destined to move on from Faulk, or would they instead keep Faulk and move someone else, like Dougie Hamilton? Players like Faulk, Schultz, and Vatanen could see their value shift in big ways depending upon how well or poorly they perform in 2019-20. Will P.K. Subban‘s arrival hurt Vatanen, or will the former Ducks defenseman thrive in a more relaxed role next season for New Jersey?

There are a lot of intriguing situations to watch there.

Notable RFAs

Josh Morrissey (Jets), Thomas Chabot (Senators), Samuel Girard (Avalanche), Mikhail Sergachev (Lightning), Ryan Pulock (Islanders), Darnell Nurse (Oilers), Brandon Montour (Sabres), etc.

These players don’t have the same leverage as they’re restricted, but it should still be interesting if there’s a ripple effect when the Jets have to pay Morrissey, and how strenuous negotiations could be between Chabot and the penny-pinching Senators. Tampa Bay’s really brought Sergachev along slowly, and you wonder if they’d be wise to try to extend him before a potential breakthrough?

***

Again, extensions will kill some of the wildest daydreams by crossing names off the list long before July 2020. Don’t assume your team will happen upon a Pietrangelo or Spurgeon.

That said, there are certain “something has to give” situations. The Maple Leafs may know that they’re only getting Muzzin and Barrie for a limited time. The Bruins have a tight squeeze happening, especially with Charlie McAvoy still needing an RFA deal this summer.

Either way, teams should savor deals like Josi at $4M, because they won’t last much longer.

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.

Maple Leafs’ Marner mum on contract negotiations

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It’s not much, but for Toronto Maple Leafs fans willing to hang on anything said by still-unsigned restricted free agent Mitch Marner, it was at least something.

When Marner stepped in front of a crowd of reporters on Thursday, he did undoubtedly knowing what the first line of questioning would be. And the second, and the third.

When is he going to sign?

“Hopefully sooner than later,” Marner said. “I want to be there for the start of camp, so hoping something can get done then.”

From there, Marner steered those questions toward his agent as he threw on his best pair dancing shoes and showed he could sidestep with the best of them.

If you’re looking for a t-shirt slogan, “You have to ask my agent” is right up there with the best of them in Toronto these days.

 

“My agent and Kyle are doing it, and they’re going to figure something out,” Marner said.

One thing Marner made pretty clear is he wouldn’t be at training camp without a contract.

“Probably not,” he said. “There’s so much risk with that. It’s just something you don’t want to risk.”

What about an offer sheet?

[ProHockeyTalk’s 2019 NHL free agency tracker]

Marner whipped out the agent line once again, while saying he’s trying to stay out of all of that “stuff.”

So the uncertainty hasn’t affected you?

“None,” he said, before once again talking about his agent’s role in the negotiations.

What about fans’ concerns that you may not sign a contract with the Maple Leafs.

“I’m leaving all of that to my agent right now,” he said.

Those agents, man. Ruining Toronto’s summer for the second year in a row.

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Marner seemed unfazed by it all and appears to be enjoying his summer.

Why wouldn’t he? He’s about to get paid in a major way, but the Maple Leafs or any number of teams that would be willing to lavish cash upon him if given the chance.

Marner’s situation is one of several playing out this summer. He’s not the only big-ticket RFA without a deal so far.

Patrik Laine in Winnipeg, Brayden Point in Tampa Bay, Mikko Rantanen in Colorado are just a few others. It’s become commonplace for big names without arbitration rights on the RFA list to let negotiations span the summer, if not further.

Marner’s contract is only illuminated better because of where he plays. Dominating two national TV broadcasters on a daily basis in Canada.

And the fear in Leafs Nations is made only worse knowing all-too-well where this path can lead.

William Nylander‘s contract last summer dragged right into the regular season and Nylander and the Maple Leafs felt those effects throughout the season.

The same scenario with Marner would be worse, given he’s the team’s leading point-getter from last season.

A Toronto native, Marner said he’s well-accustomed to the media and said his phone has been shut off for much of the summer.

Like he said, his agent is running the show. Marner’s merely the main protagonist who has yet to be revealed in a complex script.

When he will is anyone’s guess.


Scott Billeck is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @scottbilleck