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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.

The Buzzer: McDavid filets Flyers; Kane raises Sharks

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Three Stars

1. Connor McDavid, Edmonton Oilers

Look, this is Connor McDavid. He’s at the point where it’s tough to surprise us.

… Yet, I have to admit, he’s begun 2019-20 on an even hotter streak than I imagined, and for all that Edmonton might improve under Dave Tippett, it’s difficult not to chalk most of it up to McDavid, alongside Leon Draisaitl.

McDavid was outrageous on Wednesday, generating a very pretty goal and four assists for five points. Those four assists represent a career-high for McDavid.

Despite that great night, I was leaning toward giving the top star to Evander Kane until I saw this stat, which admittedly steps on the factoids section a bit:

Unless you get really obscure with a stat, it’s usually a great sign when you do something that hasn’t been done since Mario Lemieux and Wayne Gretzky were still lacing up their skates …

2. Evander Kane, San Jose Sharks

After sitting out the first three games of the 2019-20 season thanks to a suspension, Kane generated one goal and one assist in three contests. Wednesday represented an eruption for his fourth game, then, as Kane generated a hat trick during the first period of the Sharks’ 5-2 win against the Hurricanes.

Kane also assisted on a Tomas Hertl goal, giving him a hat trick plus a helper for a four-point night.

If you think Kane deserves the nod over McDavid, I understand.

That said, three stars aren’t just a great opportunity to spotlight one wonderful performance, but also a time where it’s that much more pressing to point out a hot streak and great season. Which is why we pivot to someone whose great start might slip under the radar.

3. John Carlson, Washington Capitals

When the Caps signed Carlson to an eight-year, $64 million contract, it felt like a necessary evil. We’ve seen plenty of players age poorly, and Carlson blew away his previous career totals when he generated 15 goals and 68 points in 2017-18, helping Washington win that coveted Stanley Cup.

And then Carlson put together an even better 2018-19, scoring a resounding 70 points in 80 games.

At some point he has to slow down, right?

Maybe, but so far, it doesn’t feel like that time will be at age 29. Carlson produced three points (one goal, two assists) in Washington’s win against Toronto on Thursday, giving him an eyebrow-raising 14 points in eight games.

Those 14 points leave Carlson in third place behind McDavid and Leon Draisaitl — not just among defensemen. Suddenly, that $8M AAV starts to look like a bargain for the Capitals.

The runner-up to the runner-up for Highlight of the Night

Wednesdays aren’t usually the busiest NHL days, yet this one was ripe with great moments.

The moments have been great enough that Sidney Crosby‘s bedazzling backhander already got its own post, while Sonny Milano provided ample competition with his downright silly goal for the Blue Jackets.

The bronze medal provides gold of its own, though, as Connor McDavid reminded the world why it’s pretty easy to look like a dominant team when you can basically just lob the puck up blindly and assume that it might end up becoming a goal for 97:

Factoids

Scores

PIT 3 – COL 2 (OT)
WSH 4 – TOR 3
CBJ 3 – DAL 2
EDM 6 – PHI 3
ANA 5 – BUF 2
SJS 5 – CAR 2

MORE:
• Pro Hockey Talk’s Stanley Cup picks.
• Your 2019-20 NHL on NBC TV schedule

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.

Oilers keep on rolling with win over Flyers

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Talent has never been the question in Edmonton, it was always a matter of systems and execution.

Todd McLellan and Ken Hitchcock each saw glimpses in recent years, but Dave Tippett might have unlocked the secret formula for the Oilers to have long-lasting success.

With six wins in the team’s first seven games, including a 6-3 victory against the Philadelphia Flyers on Wednesday Night Hockey, Edmonton is starting to believe that it has what it takes to become a serious contender in the Western Conference.

Jakub Voracek had two goals and an assist for Philadelphia while Carter Hart was pulled after allowing four goals on 14 shots in his first start near his hometown Sherwood Park, Alberta, as the Flyers concluded a three-game road trip through Western Canada where they went 0-2-1. Oskar Lindblom also scored.

Connor McDavid led the way offensively with five points (one goal and four assists), while Leon Draisaitl added two goals of his own as the Oilers bounced back after their first loss of the season against the Chicago Blackhawks earlier this week. Mikko Koskinen stopped 49 shots and picked up his third victory of the season.

The Oilers recorded four consecutive goals, including three in the second that broke the game wide open. McDavid or Draisaitl’s ability to break a game open has rarely been an issue, but slowing down the opposition has been problematic. But through seven games this season, the team has allowed only 17 goals thanks to improved goaltending and more importantly, better team defense.

Last season the Oilers allowed 271 goals, good for seventh worst throughout the NHL. It’s the sole reason Tippett was brought in, to limit the damage in their own end of the ice, and allow their superstars to flourish offensively without ignoring their defensive responsibility.

Tippett has opted to play McDavid and Draisaitl together for most of the season, which has always been a delicate situation. Should a coach load up to form a powerful top line, or spread the wealth throughout the lineup so a high-end player is on the ice for the majority of the game?

The Avalanche have had great success keeping Nathan MacKinnon and Mikko Rantanen on the ice as a pairing almost exclusively and the Oilers have been trending in that direction.

Ryan Nugent-Hopkins and James Neal provide options in the middle of the lineup but neither have the top-end talent equivalent to McDavid and Draisaitl.

However, if the Oilers are able to have a prolific first line, combined with strong structure throughout the neutral zone and in front of their goaltender, they will quickly become an elite team that could be a force to be reckoned with.

MORE: Your 2019-20 NHL on NBC TV Schedule

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

McKenzie on Penguins injuries, Avs contracts … spider bites?

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When Alex Galchenyuk was traded to the Pittsburgh Penguins, he likely breathed deep as he readied for a new coach, team, city, and system for the second straight season. Maybe there’s some fear about looking like a pale imitation of Phil Kessel, the other major part of that trade.

But did he factor in arachnophobia?

During a Wednesday appearance on NBCSN during the Penguins’ eventual 3-2 overtime win against the Colorado Avalanche, Bob McKenzie reported that Galchenyuk has been dealing with what could be a groin injury (or otherwise a soft tissue issue), which many surmised. What people didn’t realize is that Galchenyuk took a detour on his road to recovery because of a spider bite.

McKenzie reports that Galchenyuk had a significant allergic reaction to the bite, which seems a lot less fun than being able to climb on walls, swing on webs, and sense danger before it’s coming. (Theory: Brad Marchand may have “spider sense.” Although we’d probably need to brand it differently. “Pest-pathy?”)

Anyway, McKenzie reports that Galchenyuk is back on that road to recovery, although his precise window of recovery is unclear.

Via McKenzie, Galchenyuk, Nick Bjugstad, and Bryan Rust are essentially week-to-week still, as their windows seem to be two or three weeks. McKenzie reports that Evgeni Malkin‘s injury remains fuzzier.

Speaking of fuzziness, it sounds like the Colorado Avalanche are keeping things opaque when it comes to players on expiring contracts. So, we might need to wait-and-see with Andre Burakovsky and Nikita Zadorov.

That’s … understandable, especially with Burakovsky, who’s still making early impressions. Colorado might be wise to pick and choose with this stuff in the future, though. Could the Avalanche have signed Mikko Rantanen for less than a $9.25M AAV if they were more proactive? We can only speculate …

But hey, at least no one got bit by a spider.

*shudders*

MORE:
• Pro Hockey Talk’s Stanley Cup picks.
• Your 2019-20 NHL on NBC TV schedule

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.

Penguins remain hot with win vs. Avalanche

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Brandon Tanev notched a shorthanded goal in overtime to lead the Pittsburgh Penguins to a 3-2 victory over the Colorado Avalanche.

Sidney Crosby and Jake Guentzel also scored as Pittsburgh recorded its fourth straight victory. Matt Murray added 26 saves.

Matt Calvert and Nathan MacKinnon found the back of the net for the Avalanche but their six-game point streak to open the season came to an end.

Crosby continues to dazzle

The Penguins captain has clearly moved on from a disappointing playoff run last year, which ended in a first-round sweep at the hands of the Islanders. Instead, Crosby is off to a tremendous start, recording points in each of Pittsburgh’s seven games and leading the club on the ice to a 5-2-0 record.

Crosby netted a highlight-reel backhander to tie the game late in the first period and then assisted on a Jake Guentzel tally in the second.

The superstar center craftily tipped the puck around Erik Johnson, played the puck with his glove, and then somehow had the wherewithal to outlast goaltender Philipp Grubauer until an opening appeared for him to slide a backhander into the net.

Early in the second period, Crosby intercepted a pass at the blueline, then set up Guentzel to help the Penguins grab a 2-1 lead.

While several notable players remain sidelined, Crosby will be expected to lead the Penguins on the ice, and continue to improve the players around him. Pittsburgh will need Crosby to play at the top of his game until reinforcements return over the next few weeks.

Avalanche upcoming free agents

After the Mikko Rantanen contract issue this past summer, the Avalanche have several pending RFA’s for next summer.

Colorado is expected to be a legit Stanley Cup Contender with a great mix of dynamic playmakers, infusion of youth and seasoned veterans capable of leading the way during turbulent stretches.

However, Bob McKenzie offered that general manager Joe Sakic wants to see how the first part of the season plays out before engaging in contract talks.

Andre Burakovsky, Tyson Jost and Nikita Zadorov headline the pending RFA class and all presumably have a role to fill moving forward.

Is Lafferty here to stay?

The Penguins have been bitten by the injury bug early and have been forced to rely on their organizational depth to stay afloat during a challenging stretch.

During their Stanley Cup-winning years, the Penguins have always been able to call up a role player to fill a specific need. Is Sam Lafferty the next player to seamlessly fit in?

Lafferty was close to making the team out of training camp according to Bob McKenzie, but fell victim to the numbers game of a roster. However, injuries to five impact forwards — Evgeni Malkin, Nick Bjugstad, Alex Galchenyuk, Bryan Rust and Jared McCann — created a roster spot for him to slide in.

“We always felt like Sam was close coming into this training camp this year. But I think he has a whole lot more confidence in himself that he belongs here,” Penguins coach Mike Sullivan told the Pittsburgh Post-Gazette. “And that’s great for him, and that’s great for us.”

The 24-year-old originally from Hollidaysburg, Pennsylvania, about two hours outside of Pittsburgh, Lafferty has taken advantage of the opportunity recording five points over the previous three games.

“He’s earned his playing time. He’s just playing terrific hockey,” Sullivan said. “He made a difference every game he’s been in. As a result, he’s getting more ice time. He’s a very good penalty-killer. I think he really understands his role and is taking pride in it. You can see it every shift. He’s gaining more confidence.”

The Penguins have done an excellent job in sliding players into appropriate roles, and Lafferty is just the latest example. Does the kid have what it takes to stick around for a full season and continue to make a difference? We will find out as the season goes on.

MORE: Your 2019-20 NHL on NBC TV Schedule

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