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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.

PHT Morning Skate: Bolts need Vasilevskiy; Isles should be buyers

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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.

• The Flyers are rallying behind Oskar Lindblom after his Ewing’s sarcoma diagnosis. (NBC Sports Philadelphia)

• The Bolts need Andrei Vasilevskiy to play like he’s one of the best in the world again. (Tampa Times)

• Coaches have been getting fired for reasons both known and unknown. (Los Angeles Times)

• The Blackhawks keep finding ways to hit new lows this season. (NBC Sports Chicago)

• Jim Benning was looking to trade Sven Baertschi, but he was forced to put him on waivers. (Vancouver Sun)

• A London Knights physiotherapist helped save Tucker Tynan’s life. (CTV News)

Tom Wilson has become a new-age power forward. (Sportsnet)

• Four players from the Professional Women’s Hockey Players Association will play in the ECHL All-Star classic. (The Ice Garden)

• If good teams don’t go on long losing streaks, what does that mean for the Edmonton Oilers? (Edmonton Journal)

• Referee Tim Peel is likely done for the season after suffering a broken leg. (RMNB)

• Islanders GM Lou Lamorielllo should dip into the rental market this season. (GothamSN)

• Alexis Lafreniere is hoping to become the next future first overall pick to turn in an incredible performance at the World Juniors. (Featurd)

• It’s still too early to say that Jack Eichel is among the greatest players. (Rotoworld)

• It’s time for the Anaheim Ducks to rebuild. (Spector’s Hockey)

• Former Lightning head coach Steve Ludzik needs a liver transplant. (Tampa Times)

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.

The Buzzer: Kane’s hat trick; Staal’s milestone night

Patrick Kane #88 of the Chicago Blackhawks celebrates with Jonathan Toews
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Three Stars

1) Patrick Kane, Chicago Blackhawks

Kane surpassed Sidney Crosby for the scoring lead this decade with 16 days left in the 2010s. Since Jan. 1, 2010, Kane has 791 points (311G, 480A), while Crosby has 788 points (296G, 492A). No. 88 recorded his sixth NHL hat trick in Chicago’s 5-3 victory over Minnesota. The Blackhawks have a long way to go if they want to have a realistic shot at the Stanley Cup Playoffs, but a victory against a surging division rival is a good place to start.

2) Mark Scheifele, Winnipeg Jets

On a football Sunday, the Jets scored a touchdown in their 7-3 victory over the Philadelphia Flyers. Scheifele played a huge part with his three-point performance featuring a goal and two assists as he extended his individual point streak to six games. Neal Pionk added three assists, including two power-play helpers. The top four teams in the Western Conference (Blues, Avalanche, Jets, Stars) currently reside in the Central Division and playoff positioning will be crucial as each team eyes a lengthy postseason run.

3) Eric Staal, Minnesota Wild

Staal became the 89th player in NHL history to have 1,000 career points when he tallied a power-play goal against Chicago Sunday. After a dreadful 4-9 start to the season, the Wild have climbed up the standings with a 12-4-5 record in their past 21 games. The alternate captain leads Minnesota with 26 points, including four goals in the previous three games.

Other notable performances from Sunday:

  • Anze Kopitar’s two-goal performance in the Kings’ 4-2 victory against the Red Wings helped him surpass the iconic Wayne Gretzky for fourth place on the franchise’s all-time scoring list. Kopitar picked up his 918th and 919th point in his 1038th game.
  • Blake Wheeler finished with three points, including a goal and an assist during a four-goal barrage spanning 4:17.

Highlights of the Night

Staal etched his name in the NHL record books with this one-time blast

William Karlsson won an important foot race before Reilly Smith slid a cross-ice pass over to Jonathan Marchessault

Factoids

  • A total of 33 goals were scored across four contests Sunday for an average of 8.25 per game [NHL PR].
  • The Jets scored four goals in a span of five minutes or less for the fourth time in franchise history [NHL PR].
  • The Jets’ four goals in a span of 4:17 are their second-fastest scored in a game in franchise history, behind the mark of 3:50 set on Nov. 18, 2017 [NHL PR].
  • Canucks’ Bo Horvat has won an NHL-high 414 faceoffs this season [Sportsnet Stats].

NHL Scores

Winnipeg Jets 7, Philadelphia Flyers 3

Chicago Blackhawks 5, Minnesota Wild 3

Los Angeles Kings 4, Detroit Red Wings 2

Vegas Golden Knights 6, Vancouver Canucks 3

Sabres demote under-performing center Mittelstadt to minors

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BUFFALO, N.Y. — The Buffalo Sabres have assigned under-performing second-year center Casey Mittelstadt to the minors.

The demotion to Rochester of the AHL was made Sunday, coming a day following a 3-2 overtime loss at the New York Islanders in which Mittelstadt was a healthy scratch for the third time in four games.

The 21-year-old has four goals and five assists in 31 games this season, and limited to just a goal and an assist in his past 21. Buffalo selected the play-making center with the eighth pick in the 2017 draft following his senior year in high school.

He then signed with Buffalo and jumped directly to the NHL in making his Sabres debut immediately following his freshman college season at Minnesota.

Mittelstadt has failed to play up to early projections of developing into Buffalo’s second-line center. He has 17 goals and 22 assists for 39 points in 114 career NHL games.

Players hope U.S.-Canada rivalry game helps spawn pro league

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HARTFORD, Conn. — The United States women’s hockey team beat Canada 4-1 on Saturday night, with players hoping the first in a series of five games between the international rivals will help kindle the public’s interest in both their sport and their fight off the ice for better professional opportunities.

Canada’s Victoria Bach and the Megan Keller of the U.S. traded power-play goals in the first period, before Amanda Kessel put the U.S. on top for good with a player advantage in the second. Abbe Roque’s backhand in the period gave the US a 3-1 lead and Alex Carpenter beat Genevieve Lacasse for the final goal 1:15 seconds later.

More than 7,000 fans showed up for the international competition, which comes after more than 200 members of what has since become the Professional Women’s Hockey Players’ Association announced in May they would not play professionally in North America during the 2019-2020 season.

“I think it’s important for people to watch us play and see the level of talent and entertainment that’s out there,” Kessel said. “It’s getting that understanding that we need to help get us a place to play year-round so that people can see us more than five times a year.”

The women are seeking a professional league that provides a living wage, health insurance, infrastructure and support for training. The Canadian Women’s Hockey League shut down in the spring after 12 years of operation, leaving only the five-team National Women’s Hockey League, where most players make less than $10,000 a season.

“The product is there,” Kessel said. “The people to watch it are there. We just need a structure set in place.”

Sarah Nurse, a forward for Team Canada, whose cousin Kia Nurse plays for New York in the WNBA, said players are hoping to get support from the NHL, which has, so far, expressed little interest in investing in a women’s league.

“We can look at (the WNBA) and see that women’s sports have value and they have a place in this world,” said Nurse, who made $2,000 last season playing in the CWHL. “That is definitely a model that we look to.”

The rivalry series was created after the Four Nations Cup in Sweden was canceled when top Swedish players pulled out of national team events due to concerns over their salary and working conditions.

Without a viable pro league, players who are out of college have been training on their own at random rinks across North America in between gatherings of the national teams or training sessions and exhibitions sponsored by the players association.

Canada won two of those over the US in Pittsburgh last month.

But the lack of consistent competition can stunt the players’ development, especially when it comes to be being prepared for world and Olympic competitions, the players said.

“It’s very unfortunate,” Nurse said. “Games are when we truly get better and test out our skills, so it’s unfortunate that we don’t have more games to play.”

Cayla Barnes, who plays defense for the U.S. team and Boston College, said she and the other college players on the national teams understand what is going on and appreciate what the older players are doing.

“They are putting so much on the line for the younger generations,” she said. “Not just for us college kids who are coming up, but for U-8, U-10 girls who are coming up so they have opportunities later on. So I think all of us who are younger are trying to support them in whatever way we can.”

Hundreds of girls wearing their youth hockey jerseys attended the game, chanting “U-S-A” as the final seconds ticked off the clock.

“I want to be like them, like in the Olympics when I get older,” said 14-year-old Leila Espirito Santo, of Glastonbury “I started playing when I was in fourth grade and I wasn’t the best, but watching them play made me want to be better. It showed me I could do it.”

The teams will meet again on Tuesday in Moncton, New Brunswick. Other games part of the 2019-20 Rivalry Series are slated for Feb. 3 and Feb. 5 in Vancouver, British Columbia, and Feb. 8 in Anaheim, California.