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.

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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.

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