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, 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.
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 dolike 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.
It was nearly four years to the day that the Edmonton Oilers organization was in a nearly identical position as the one it found itself in on Tuesday, where a recently hired general manager — a highly regarded, Stanley Cup winning general manager — was holding a press conference to announce the hiring of a veteran head coach with a strong track record of success in the NHL.
In 2015, the cast of characters included Peter Chiarelli introducing Todd McLellan, a duo that was supposed to lead a perennial dumpster fire of an organization out of the ashes by providing some much-needed stability and building something around the NHL’s next great superstar (Connor McDavid) that fell into their laps.
Obviously, things did not go anywhere as planned and the organization was forced to smash the reset button once again over the past year. That reset process continued on Tuesday when Ken Holland introduced Dave Tippett as the 16th coach in franchise history, and the eighth in just the past 10 years.
The job for these two is a significant one as they attempt to build something out of an organization that has missed the playoffs in 12 of the past 13 seasons, including a 2018-19 team that wasn’t even a close to a playoff spot in a watered down Western Conference despite having two of the league’s top-five scorers (McDavid and Leon Draisaitl) on its roster. It takes a special kind of failure to miss the playoffs under those circumstances, but this team managed it.
At the introductory press conference on Tuesday Tippett and Holland hit all of the usual buzzwords new coaches and managers love to use in these situations, including stability, communication, and structure. Holland praised Tippett’s experience and talked about him being one of his leading candidates throughout the entire process.
Tippett also expressed optimism that the situation isn’t as bleak as it seems from the outside, saying “everyone talks about McDavid and Draisaitl, but there are more pieces here than McDavid and Draisaitl. There is a lot here to build on.”
From a hockey standpoint, Tippett at least sounded like someone that has his finger on the pulse of the current NHL and what it takes to win.
He spoke of needing scoring depth including a fourth-line that can provide offense.
He talked about the necessity of a five-man attack on the forecheck and having defenders that can not only move the puck out of the defensive zone and through the middle of the ice, but also get involved in the offensive zone.
He also fought back at the suggestion that he is a “defensive-minded coach” and talked about finding out what his players do best, putting them in a position to succeed, and maximizing their potential. In other words: He’s not planning on going to Edmonton and trying to force his roster into a set system, but rather build a system around the roster he has.
“I laugh at that all the time,” said Tippett in response to a question about his reputation as a defensive coach. “My first [head coaching] job in the NHL, I got from Doug Armstrong in Dallas because I was an offensive coach and they hired me because they thought I could bring some new ideas. We had some pretty good offensive teams in Dallas, but when I got to Arizona we had to figure out how to win without those guys. I don’t look at myself as a defensive coach or an offensive coach, I look at myself as a coach that tries to win with what I have.”
So what does he have to work with in Edmonton?
For starters he has a McDavid-Draisaitl duo that dominated their ice-time together last season. When asked whether he would prefer to see them as a duo on the same line or separated where they each center their own line, he spoke glowingly of their ability to feed off of each other and seemed to indicate that he sees them on a line together. And that is probably the right move because there was almost no other duo in the league that did more last season than those two.
Assuming he keeps those two together he still has Ryan Nugent-Hopkins (barring an offseason trade, which would be a bad idea for the Oilers) as a more than suitable No. 2 center.
After that? There is a significant drop in talent and will probably take him back to his early days in Arizona where he had to figure out a way to win with a patchwork roster.
The defense is severely lacking in the type of players he talked about when it comes to joining the rush and moving the puck.
The scoring depth beyond the top-three forwards rapidly falls off a cliff, as shown by the fact McDavid, Draisaitl, and Nugent-Hopkins combined to score 52 percent of the team’s goals during the 2018-19 season. The depth was so bad that when none of those three were on the ice during 5-on-5 play the Oilers were outscored by a 45-26 margin. They were not just bad, they were not even competitive.
There is only so much a coach can do to remedy that, and while Tippett had some early initial success in Arizona, making the playoffs in three consecutive years including a stunning trip to the 2011-12 Western Conference Final, the lack of talent at his disposal eventually caught up to him in the latter years of his tenure when the Coyotes missed the playoffs in his final five seasons with the team.
And that brings us to the key point here with the Oilers — their success or failure probably isn’t going to be determined by what Tippett does or does not do as a coach. There is very good reason to believe that he is a good coach. HIs approach seems sound. He has had success in two different cities, won more than 550 regular season games as a head coach, and taken teams deep into the playoffs on more than one occasion.
But the Oilers have had successful coaches come through and fail before him.
Todd McLellan’s resume before his time in Edmonton was a strong one, but he couldn’t win with the Oilers.
Neither could Pat Quinn, Tom Renney, Ralph Krueger, or Dallas Eakins. Not all of them were bad coaches or bad hires. Sometimes it’s more than the coach, and when this many coaches come through one organization in such a short period of time and all experience the same fate it is probably a good sign that the problems start much higher than behind the bench.
As much as Tippett — or any coach — likes to pride themselves on coaching up players and “just finding ways to win” it is still a talent driven business, and the Oilers as presently constructed just do not have anywhere near enough of it. That puts almost all of the pressure not necessarily on Tippett, but right back on Holland to build something out of this team and give his new coach enough to work with around the McDavid, Draisaitl, and Nugent-Hopkins trio.
If Holland can do that, Tippett might very well be the right coach for the Oilers and one that can succeed where so many before him have failed.
If Holland can not do that, we will probably find ourselves doing the exact same thing in another couple of years where another freshly hired, big-name general manager is introducing the next highly respected veteran coach.
New Edmonton Oilers general manager Ken Holland has found his head coach and has hired Dave Tippett to help turn the franchise around.
“Dave brings a wealth of experience and knowledge to the organization,” said Holland in a statement. “He is a great communicator and has consistently led teams known for their level of compete. I look forward to seeing Dave guide the Oilers this fall and we are all excited to have him on board.”
Tippett, who gets a three-year deal with the Oilers, had been working with the NHL Seattle expansion group as a senior advisor since June 2018. Before that, he worked for 14 straight seasons as a head coach with the Arizona Coyotes and Dallas Stars. He won the 2010 Jack Adams Award in his first season with Coyotes, helping to snap the franchise’s six-year playoff drought and managed to get a lot of out a roster that didn’t exactly have the highest budget.
In speaking with The Athletic’s Craig Morgan earlier this month, Tippett, who reportedly interviewed for the head coaching job with the Buffalo Sabres, didn’t close the door on a return behind the bench. It’s a long wait until the 2021-22 season, which will be Seattle’s first in the NHL.
“I don’t think that coaching fire ever goes out, but we’ll have to see how things play out,” said Tippett, who will become the Oilers’ eighth head coach in the last 12 seasons. “If an opportunity comes along, it’s like anything in life. You look at that opportunity. It’s just like this opportunity in Seattle. I looked at it and it looked pretty good.”
Big on structure, Tippett’s Coyotes teams were known for being strong defensively early on in his tenure. The Oilers employing Connor McDavid and Leon Draisaitl are two good offensive pieces to start with up front. The work on the back end is something that needs improving in Edmonton, but much of that change will fall in Holland’s lap as he tries to get the team in better shape salary cap-wise.
But if you’re Oilers CEO Bob Nicholson and your goal is to make a rebuild into a quick transition back into a playoff team, is Holland the right choice? He has four Stanley Cups on his resume while running the Red Wings, sure. But once the franchise’s golden generation reached their golden years in the NHL, that success came to an end, and there were no younger reinforcements coming through the Red Wings’ system to sustain those years of winning, at least not immediately.
One of the things Holland was known for during his time in Detroit was allowing prospects to develop properly in the AHL, even if some thought those players were well-beyond ready for the NHL.
Three of the Red Wings’ top five scorers this past season probably could have been up earlier in the NHL considering the franchise was and remains in a transition phase after the end of their 25-season playoff streak. Andreas Athanasiou spent parts of three seasons in the AHL before becoming a full-time NHLer. Anthony Mantha needed extra time to find the scoring touch that served him well in junior and has posted back-to-back 20-goal seasons. Tyler Bertuzzi broke out this past season with 21 goals after finding his way through 137 games in Grand Rapids.
Jesse Puljujarvi had a roller coaster of a 2018-19 season. Kailer Yamamoto got in 17 games with the Oilers. Caleb Jones and Cooper Marody have accumulated good experience with the Bakersfield Condors. Evan Bouchard is coming soon. Those are the prospects the Oilers need to get right if they’re going to have any impact at the NHL level. Letting them overripe in the AHL would serve them well as opposed to yo-yo’ing them between levels, messing with their development.
But while prospect development could be looked at as a positive, some of the contracts Holland has handed out has ended up handcuffing him while attempting to maintain their status as a playoff team. Justin Abdelkader, Frans Nielsen, Darren Helm, Trevor Daley, and Jonathan Ericcson are some of the term-heavy, cap-eating deals that have helped put the Red Wings in the position they currently reside.
That track record can be improved if Holland surrounds himself with smart people. Pat Verbeek, who was a pro scout with the Red Wings under Holland, is leaving his role as assistant GM in Tampa to return to Detroit in the same position under Yzerman. But will the same be said for Tyler Wright, who currently works as the Red Wings’ director of amateur scouting?
Then you have the question of the head coach now that Ken Hitchcock will not be back and possibly moving into an advisor role. Dave Tippett seems itching to return behind a bench and doesn’t want to wait for Seattle’s NHL entry. Dan Bylsma was an assistant in Detroit this past season. Jay Woodcroft has done a great job in his first season with the Oilers’ AHL affiliate in Bakersfield.
There will be plenty of options available to replace Hitchcock.
Nicholson and Oilers owner Daryl Katz feel Holland is ready for a successful second act as an NHL GM. They are, of course, also desperate to ensure time isn’t wasted while McDavid is still posting 100-point seasons. There’s plenty of work ahead for Holland to make that a reality, and this move cannot fail and set the franchise back any longer.