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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.

Devils should go bold, and not just to keep Taylor Hall

Winning an NHL Draft Lottery should attach a rocket to your team’s hopes, especially when you land that top overall pick even though you don’t have the best odds.

Yet, Taylor Hall‘s been here plenty of times before, so forgive him for not looking at a draft lottery win as a cure-all. Instead, through his time seeing the Edmonton Oilers, and now the New Jersey Devils, landing unexpected No. 1 overall picks, Hall’s name has been associated more with memes (also: “the trade is one for one”) than with being one of the best wingers in the NHL.

The one-time Hart Trophy winner couldn’t help but lean into the jokes himself after the Devils landed the top pick of the 2019 NHL Draft:

No rush on extension

The Fourth Period’s Dave Pagnotta created a stir with a report that mentioned that “as of now,” Hall isn’t interested in signing a contract extension with the Devils, which he would be able to do by July.

Hall, 27, addressed the rumblings, telling The Athletic’s Arpon Basu (sub required) that he’s confused that it would be such big news that he’s simply not in a rush to sign an extension. Hall’s agent and Devils GM Ray Shero made the same general points about there being no real rush to NHL.com’s Mike Morreale.

“We never really looked at July 1 as a deadline and Ray hasn’t looked at it like that either,” Hall said to Basu.

One key point people emphasized from Pagnotta’s report, either way, is the phrasing “as of now.”

In a way, you almost wonder if a light bulb was going off over Taylor Hall’s head as he watched Kawhi Leonard’s situation play out with the Toronto Raptors. Despite being an excellent scorer and player basically since his first NHL game, Hall’s only been to the playoffs once, and that was thanks to his Herculean Hart season where he dragged the Devils into the 2018-19 postseason. Why shouldn’t Hall wait and see if the Devils can actually contend before signing away his rights to hit the open market? As Hall’s agent Darren Ferris mentioned, some players only get one chance to truly sign the contract they want with the team they want to play for – without the artificial bindings of RFA status, and without the aging curve limiting their demands. Hall deserves to explore his options as much as just about anyone else, so it only makes sense that the Devils would need to be really convincing to lock him up for what would could be the rest of his prime.

Got to be smart to take advantage of being lucky

The thing is … the Devils should be aggressive to improve, even if Hall’s $6M cap hit wasn’t expiring after 2019-20.

While Hall’s Oilers blundered despite winning multiple draft lotteries, the Devils should view Jack Hughes’ or Kaapo Kakko’s rookie deal as a window of sorts. You can compete beyond that potential three-year entry-level contract, but you’ll never enjoy savings like these again with whoever the Devils pick first overall on June 21.

Consider that:

  • The Penguins won their first Stanley Cup of their current era (in 2008-09) when Evgeni Malkin and Jordan Staal were in the final year of their rookie contracts, and made it to the previous Stanley Cup Final in the last year of Sidney Crosby‘s rookie deal.
  • The Blackhawks won their first Stanley Cup of their run (in 2009-10) during the final year of rookie contracts for both Patrick Kane and Jonathan Toews.

The Toronto Maple Leafs could still compete for years thanks to the bounty of talent they’ve accrued, yet the 2018-19 stings a bit extra because it represents the end of those rookie contracts for Auston Matthews and Mitch Marner.

So, really, the Devils have two directives to get aggressive during this offseason. First, adding more talent can show Taylor Hall that they’re serious about competing, after Shero’s (wisely) taken the slow-and-steady approach before. Secondly, with Jack Hughes/Kaapo Kakko, the Devils could have a difference-maker on a limited contract for three seasons.

A ton of cap space for Devils

While the Devils have a lot to work on – this post from January lays out big issues for their rebuild, including goaltending – Ray Shero has plenty of ammo to use if he wants to be bold. Which, again, the Devils should be, what with that top overall pick and the need to woo Hall.

As you can see from their Cap Friendly page, the Devils have a ton of cap space to work with, as they have an estimated $35.6M in space with 14 roster spots covered. Will Butcher is really the only truly prominent free agent to deal with, although Devils fans might interject with a Stefan Noesen or two.

Yes, Shero must be cognizant of future decisions. Along with Hall being up after 2019-20, Nico Hischier only has one year remaining on his entry-level contract, Sami Vatanen is also entering a contract year, and Kyle Palmieri‘s bargain $4.65M cap hit expires after 2020-21.

But, for the most part, the Devils boast as close to a clean slate as you can hope for in the modern salary cap era, and now is the time to really start taking advantage.

Trades, free agency … offer sheets?

While the free agent route is fascinating and more straightforward (is Newark close enough to New York for Artemi Panarin?), Shero can also get creative.

The Devils have three second-rounders and two third-rounders to go with their normal choices in the 2019 NHL Draft, so Shero could use those picks to swing trades for roster players or try to move up in the draft.

Maybe just as tantalizingly, the Devils’ bounty of 2019 NHL Draft picks could also make them more comfortable with the idea of forking over picks to go the offer sheet route. What if the Devils presented Hall with the opportunity to play with, say, Hughes/Kaakko, Hischier, and Mitch Marner or Brayden Point in the future?

Admittedly, offer sheets are a “believe it when you see it” proposition in the risk-averse NHL. Still, the Devils are one of the teams that are best situated to make such a move, as they have the cap space, the urgency to improve, and the requisite picks to hand over a challenging offer sheet.

(All About the Jersey’s CJ Turturo has a fantastic deep dive on offer sheets and how they relate to the Devils, which also understandably emphasizes that it’s an unlikely route.)

***

Don’t get me wrong; it makes sense that Devils fans might feel a little frightened here. There’s the nightmare scenario where Hall leaves the Devils for nothing, much like what happened with John Tavares and the Devils’ buddies on Long Island.

But, really, this situation should give the Devils another push to be aggressive – and maybe even creative – to get better, fast. Even if Hall isn’t a part of the longer solution, the Devils were gifted with the No. 1 pick, and should take advantage of the significant competitive advantage you can enjoy in competing while key players are on entry-level contracts.

If that aggressiveness impresses Hall enough to stay, then it’s all gravy … or sauce.

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 extend Shanahan’s contract through 2024-25

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The Toronto Maple Leafs announced an important contract extension on Tuesday, but no, it’s not for Mitch Marner.

Instead, it’s for the man behind the plan to bring in players like Marner. The Maple Leafs handed Brendan Shanahan a six-year extension as team president (and alternate governor), which means that extension runs through 2024-25.

It’s easy to get lost in the particulars of the contract squabbles involving Marner and William Nylander, and two straight postseason defeats to the Boston Bruins, and forget that the Maple Leafs have come a long way since bringing in Shanahan in April 2014. The team’s press release does a nice job of quickly summarizing that success:

The 50-year-old native of Mimico, Ontario first joined the club in April 2014. Since then, the Maple Leafs have earned three consecutive playoff berths (2016-17 through to 2018-19), while recording their most points in a single season (105 in 2017-18) and consecutive 100-point seasons (2017-18 and 2018-19) for the first time in franchise history.

The “Shanaplan” involved bringing in Mike Babcock as head coach and convincing Lou Lamoriello to come aboard, and then eventually pass the torch as GM to Kyle Dubas. During that time, the Maple Leafs have made some significant moves, most notably landing John Tavares in free agency.

Of course, the biggest tests lie ahead.

The Maple Leafs must solve the riddle of the Marner contract situation, and the salary cap crunch that is likely to result. Who will they trade to make room for the bigger names, or will this situation demand that the Maple Leafs trade a big name to make it work? Dubas likely carries the heaviest burden in making all of that work, but Shanahan’s almost certain to have some say, even if it’s more of a big picture outlook.

Dubas did what he could to squash rumblings about Babcock’s future, explaining that the Maple Leafs “are all in on Mike, and Mike is all in on us.” Still, the perception is out there that the head coach and GM diverge on some key matters when it comes to running a hockey team, and those rumblings will grow louder during every inevitable rough patch in 2019-20, and possibly beyond.

[Babcock did what he could to clear the air during a volatile time in March.]

Toronto Marlies head coach Sheldon Keefe also hovers in the background, in part because he might buy into Dubas’ vision more than Babcock, but also because other NHL teams might try to snatch him up as their next head coach.

So, basically, Shanahan faces difficult challenges both on the ice with cap management and behind the scenes with managing people. This has largely been a success when it comes to rebuilding a lump of clay (or worse) into a consistent playoff team, yet it’s arguably even more difficult to make the leap from “good” to “great.”

There could be many more growing pains along the way, but overall, it’s easy to see why the Maple Leafs have so much faith in Shanahan, and the Shanaplan.

(We might be getting to the point where it’s time to retire Shanaplan, though, as great as that word splice is.)

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.

Tavares injures side and will miss worlds for Canada

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TORONTO (AP) — Maple Leafs center John Tavares injured his side while practicing with the Canadian team and will miss the upcoming world championships in Slovakia.

Hockey Canada said Thursday it contacted the Maple Leafs and it was agreed it was best for him to return to Toronto for further evaluation of his oblique.

Such injuries usually require at least a few weeks of recovery. It wasn’t immediately clear how the 28-year-old star was hurt.

The news on Tavares came shortly before the Maple Leafs said defenseman Travis Dermott will have shoulder surgery and miss at least six months. He won’t be available until mid-November at the earliest.

Dermott had four goals and 13 assists in 64 games this season, plus a goal and two assists in seven playoff games.

Tavares was one of the few stars on Canada’s roster. He had a career-high 47 goals with 41 assists in 82 games during the regular season. He added two goals and three assists in the playoffs.

Tavares has played on three previous world championship teams. He was on Canada’s championship team at the 2014 Olympics, where he injured his left knee and missed the rest of that NHL season.

Canada opens world championship play against Finland on Friday.

No punishment for Bruins’ Marchand, who doesn’t ‘regret’ cheap shot

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Boston Bruins star-miscreant Brad Marchand isn’t expected to face supplemental discipline for his very Brad Marchand sucker-punch of Blue Jackets defenseman Scott Harrington, according to The Athletic’s Aaron Portzline.

If you’re hoping that Marchand might have “learned” something from this experience, well, you haven’t been paying much attention, have you?

Marchand admitted to The Boston Globe’s Matt Porter that his punch to the back of Harrington’s head (while Harrington’s back was turned, and he was off his feet), was “unnecessary,” … but Marchand also said that he doesn’t regret doing it, explaining it away as “playoff hockey.” Then cue some whataboutism, in regard to Columbus apparently roughing up Jake DeBrusk.

To Harrington’s credit, he’s not throwing gas on the fire. Instead, he called it a “hockey play” and emphasized that the Blue Jackets are moving on, as NBC Sports Boston’s Joe Haggerty reports. (This article has even more on Harrington brushing it off.)

Allowing Marchand to be his own worst enemy?

You may chalk this up as “living well is the best revenge.”

The Blue Jackets have won two consecutive games to snare a 2-1 series lead against the Bruins in Round 2, including Tuesday’s strong Game 2 effort.

Bottling up Marchand, Patrice Bergeron, and David Pastrnak has been a big part of Columbus’ success. Marchand specifically is on a four-game pointless streak, stretching back to Game 7 of Round 1 against the Maple Leafs, and he must be getting frustrated being that he’s failed to score a goal despite generating nine shots on goal against Sergei Bobrovsky over three games.

While going without a point, Marchand’s taken two penalties, and both resulted in power-play goals for the Blue Jackets. Sportsnet’s Chris Johnston reports that the Bruins are planning on having a talk with Marchand about discipline.

Honestly, it’s hard not to chuckle at the thought of the Bruins having what must be the billionth “talk” with Marchand about his antics.

Years ago, even stretching back to the later days of the Peter Chiarelli era in 2014, there were rumblings about Marchand being traded, in large part because of his sometimes self-destructive tendencies. Marchand’s ascent from a very good player to a full-fledged superstar has been aided by a better balance of scoring versus shenanigans, yet it sure seems like it’s too much to argue that he’s fully reformed.

(Granted, his playoff lick count appears to be at zero, unless we’ve missed some sneaky snacking.)

All things considered, the Blue Jackets are being pretty smart here. Sure, some of John Tortorella’s no-comment approach is to avoid fines for officiating, but if this side stuff gets Marchand off of his game and into the penalty box, that could be the sort of factor that helps Columbus win a Round 2 series that’s been very extremely close so far.

In other words, the Blue Jackets may profit off of a “don’t feed the troll” approach.

Teaching moment

Onlookers have been quick to voice their disapproval, however.

USA Today’s Kevin Allen believes that a suspension is warranted, considering Marchand’s history. Even those who argue that it wasn’t suspension-worthy also called it “greasy” or even “a greasy rat play.”

The “it is what it is” feeling spreads when you realize that sneaky punches do happen quite often during these scuffles. The Blue Jackets experienced this before when Steven Stamkos snuck a shot in on Nick Foligno (note Foligno’s death stare), and plenty was made of Zdeno Chara landing a punch on John Tavares.

“These things happen” makes it tough to suspend Marchand, yet maybe this moment could inspire some broader change? What if the NHL decides during the off-season to ramp up punishments for these types of moments, particularly involving punches to the head, especially as we gain more awareness of the dangers of head injuries? Would other players – not just recidivists like Marchand – really take the chance to throw unnecessary punches like those if there was a more credible threat of a suspension?

***

Whether he’s getting under the Blue Jackets’ skin, scoring goals, or having a meltdown while failing to accomplish either task, it should be fascinating to watch Marchand in Game 4 and as this series goes along. Just don’t expect some big change of heart from one of the most prolific pests of the playoffs.

Game 4 goes at 7:30 p.m. ET on Thursday on NBCSN (Stream live).

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.