6 Choices for Oilers on the future of Ken Holland

General Manager Ken Holland and Chairman Bob Nicholson of the Edmonton Oilers (Photo by Bruce Bennett/Getty Images)
General Manager Ken Holland and Chairman Bob Nicholson of the Edmonton Oilers (Photo by Bruce Bennett/Getty Images)
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TORONTO, ONTARIO – NOVEMBER 12: Ken Holland takes part in a press opportunity prior to his induction into the Hockey Hall of Fame at the Hockey Hall Of Fame on November 12, 2021 in Toronto, Ontario, Canada. (Photo by Bruce Bennett/Getty Images)
TORONTO, ONTARIO – NOVEMBER 12: Ken Holland takes part in a press opportunity prior to his induction into the Hockey Hall of Fame at the Hockey Hall Of Fame on November 12, 2021 in Toronto, Ontario, Canada. (Photo by Bruce Bennett/Getty Images) /

Ken Holland’s contract is expiring at the end of the season. There are several ways for this to go for the Oilers, but how will it end?

It’s no secret that Ken Holland’s contract with the Oilers is up after this season. We’ve heard many scenarios that could play out in terms of what he’s going to do afterwards. Publicly, Holland has remained tight-lipped as he said he doesn’t know exactly what he’s going to do, but word is he’s contemplating retirement. He is 68 years old after all, and he has children and grandchildren plus an off-season home in Vernon, BC, so I’m sure he would appreciate more time with his family in his senior years, as do many seniors.

That being said, for anyone who has had success in the NHL, they are a bit of a different breed. This is a sport that most involved in the game are so passionate about, it’s really in their blood and they crave the challenge, whether they are a player, executive, scout, etc. So for these folks while retirement may hold some appeal, they could foresee themselves being miserable in retirement after having walked away from the game of hockey.

I’m not Ken Holland and I don’t know him personally, so which of these types of people he is I can’t be sure, but one thing’s for sure, there’s a variety of places this could go.

Let’s investigate those now.

1) Oilers fire Holland 

IMO this would be an overly harsh way to treat the guy who has guided the Oilers to more success than almost all of his predecessors outside of Kevin Lowe and Glen Sather. Some of the more ignorant honey badger types amongst the Oilers fanbase were calling for Holland’s head during the losing streak and unsurprisingly those voices have been silenced now that the team is winning again.

It’s also important to note that Holland has now been GM of the Oilers for four full seasons, and they have made the playoffs all four seasons. Yes, they haven’t won a cup yet or even gotten to the finals, but they do have series wins to show for it, including an extra sweet one over the Calgary Flames, so there is a track record of success there. Then there are things like the historic power play they had last season that set new NHL records – even Sather never guided the Oilers to that during the dynasty years in the 1980s.

As for this season, that remains to be seen. Even if the Oilers don’t make the playoffs though, most teams would take four out of five seasons in the playoffs and multiple series wins from their GMs.

The Oilers aren’t even that far away from being in the mix either after Friday night’s win over the Wild, as they moved above the Kraken in the Western Conference standings. One more win from the Oilers and one more loss by the Flames and they would leapfrog over their rivals. (The Oilers would have one more win than the Flames, which would be the tiebreaker). At that point, they would potentially only be three points out of a wildcard spot and 10 out of a division spot, with more than 50 games remaining. The Oilers are also the hottest team in the league right now – no other NHL team is on a six-game winning streak. So honestly, I like our odds right now.

And that’s not even getting into Holland’s track record at the helm of the Detroit Red Wings – 20+ consecutive years of playoff appearances and multiple Cups. If you were calling for him to be fired during the losing streak, then you must have the integrity to give him credit when things are going well. At least be consistent in your emotional response.

Holland has a knack for being an NHL GM, and that’s not something you just throw away. That being said, it’s worth noting that since the man who hired him (Bob Nicholson) has faded away from Oilers chairman to an advisor and alternate governor position, the Oilers now have a guy at the top of the executive ladder – Jeff Jackson – who has a GM that is not his hire. That means Holland’s position is less secure than when he was hired, as it’s a well known fact that all NHL hockey operations people like to bring their own people with them.

Yes, not every move Holland’s made has worked out — I’m sure he’d like a mulligan on the Jack Campbell contract at this point — but when he was first hired he publicly said not every move he made would work out. To be fair, I don’t think any GM can claim that, but it’s safe to say his moves have worked out more often than not, which is what he set out to do.

(Photo by Jeff Vinnick/NHLI via Getty Images)
(Photo by Jeff Vinnick/NHLI via Getty Images) /

2) Holland’s contract is not renewed at season’s end

IMO this would be incredibly short-sighted as well, to even consider. As previously mentioned, Holland already ranks as a top three GM in team history, and with his track record between here and Detroit, he’s earned the right to control his destiny.

That being said, as also previously mentioned this is the perfect opportunity for new(ish) CEO Jackson to install his own guy at the top – and he probably won’t have that opportunity for many years to come unless his pick crashes and burns. When Jackson is deciding from the club’s perspective at the end of the season, this has got to give him pause.

That being said, if Jackson is as good a leader as his reputation says, he’s got the integrity to realize that perhaps what’s best for the team is to stick with the status quo, even if Holland was not his hire but Nicholson’s. Good leaders don’t let ego make decisions for them.

Just because Holland wasn’t Jackson’s hire, it doesn’t mean he should be automatically pushed out the door. It doesn’t mean he should automatically stay, either, but he shouldn’t be ushered out the door without serious thought as to what the club is giving up.

Here’s a variation on this:

3) Holland decides to voluntarily step aside and retire

At 68, Holland must see this as at least something to think about. By the end of his contract, he’ll have made $25 million from the Oilers alone, not including the wages from his days in Detroit.

Money is certainly no object, and unlike in his latter days in Detroit, he no longer has a meddling owner forcing him to keep the team at a certain place. Darryl Katz is well on board with whatever his people on the Oilers want to do. So we know from history that when this team’s window to win slams shut, Katz will support the team’s direction on the next rebuild and not be like the “old white guys” club that comprises Flames ownership, who are only worried about the bottom line and not the team’s success.

Only Holland knows if he’s ready for this or not – if the Oilers do end up winning the cup at the end of this season I could see this being Holland’s number one option, as he’ll have accomplished his goal of bringing the cup back to Edmonton. If the Oilers don’t win the Cup, I could see him being more inclined to come back.

On the other hand, maybe he’s not ready to retire regardless of team success.

(Photo by Bruce Bennett/Getty Images)
(Photo by Bruce Bennett/Getty Images) /

4) Holland changes roles

If Holland wants to continue on in hockey operations but is not ready to step away into retirement altogether, this would definitely be the next option for him. Nicholson has already done this, moving down from Oilers chairman to Special Advisor and Alternate Governor, Hockey Operations.

Would Holland be next to take more of a backseat? Detroit tried to promote Holland to the franchise’s president five years ago and he only lasted mere months in that role, before jumping ship to the Oilers as GM. Of course that was five years ago; times change, people change. Is Holland ready to ride off into the sunset with one foot into retirement?

Maybe. At this point, only he knows that. Perhaps stepping into a lesser role at his age would be beneficial to him in many ways, not the least of which is physically and mentally. But, I’ve seen others his age get insulted and offended when presented with this option, even when it seems like it’s something they might want.

Some people are not built for retirement, they have the energy and desire to keep working until they’re dead. Holland is not like Peter Chiarelli, he doesn’t withdraw into himself for no reason and stop taking advice from others. In fact, from what I’ve heard he actively seeks it from the rest of his management group.

Some people aren’t happy being in a lesser role, as they have to be the ones in charge. I can’t say for sure if Holland is this type or not.

5) Holland comes back but for a shorter contract

Perhaps retirement is on Holland’s radar but just not right now. Maybe he still wants to run the show, but not for five years again.

Maybe he signs on for only two or three seasons instead of five. This would probably be the most beneficial option for the Oilers from their perspective, as it would give them some time to groom a replacement for Holland. All we know at this point is it won’t be Steve Staios, since he’s jumped ship to Ottawa where he has history with the new ownership group there.

If this happens it’ll probably be Holland’s idea since, as I previously mentioned, he’s earned the right to determine his own fate to an extent.

And now for the most obvious choice……

(Photo by Bruce Bennett/Getty Images)
(Photo by Bruce Bennett/Getty Images) /

6) Holland comes back for another five years

Holland was at the helm when Detroit won three Stanley Cups, so he’s felt the high of winning the Cup as an executive. There are very few clubs where he has a better chance to do that than here in Edmonton, with the two best players on the planet signed and sealed.

If Holland is the energetic, go-go-go type that always needs to be active and in the thick of things, he might want to stick with the status quo despite being 68 years old. He clearly hasn’t lost his touch and even though his Oilers teams have experienced some success they still haven’t won the ultimate prize, and for some hockey people that’s the kind of thing that can really gnaw at you. Based on his experience in his last days in Detroit, I have to believe at least part of that is still present with his current self as GM with the Oilers. Maybe not, but I have a gut feeling it might still be.

Holland has never once struck me as a guy who’s sick of his job or overwhelmed by it. He always seems to relish the challenge of improving his team in any way possible, in improving the cap situation, in making the appropriate moves at the trade deadline and in the offseason.

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In the short term, he’ll have to undo his mistake on Campbell, whether that gets fixed with a trade or not. He would no doubt like to shake up the bottom six a little. Ryan Mcleod has really come on the last two games, but other than him by and large the bottom six hasn’t been able to consistently deliver offence the same way they did last season.

Then on D, there’s the question of what to do with Philip Broberg and the soap opera he and his agent have created.

I don’t know if a GM is ever really satisfied with his team, and Holland just strikes me as that guy who would have a lot of regret walking away from the job at the wrong time.

If he can deliver a cup, or two, or three between now and when his next contract is up, perhaps Holland may be ready to call it quits at that point, or maybe he won’t quit until Connor McDavid and Leon Draisaitl retire, and leave the job of a rebuild to someone else.

Next. Top 3 Oilers from comeback win over Wild. dark

If Holland can deliver three Cups to two different NHL franchises, he would most definitely go down as one of the most legendary GMs of all time. That’s got to hold some compelling sway for him. At any rate, we’ll see what happens after the season is up, as we’ll probably never really know until then.

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