Make or break time for Ken Holland with the Edmonton Oilers

Ken Holland has enjoyed plenty of success as a general manager in the NHL, but time is running out for him to bring a long overdue Stanley Cup to Edmonton.

Ken Holland has a sterling reputation, which includes three Stanley Cups as general manager with the Detroit Red Wings and being inducted into the Hockey Hall of Fame as a builder. (He also won a Stanley Cup in Detroit as assistant GM.) And yet, he’s come to the crossroads of his tenure with the Edmonton Oilers.

There’s a lot on the line for Holland, as he enters the final season of his five-year, $25 million contract with the Oilers. Brought in to help the franchise return to Stanley Cup glory, he’s yet to succeed in his primary mission.

Yes, the Oilers have been to the playoffs in all four seasons the former goaltender has been general manager and president of hockey operations. However, the furthest the team has gone is the Conference Finals in 2021-22, where they were swept 4-0 by the eventual Stanley Cup champion Colorado Avalanche.

Interestingly, the Oilers were also knocked out by the eventual Stanley Cup champions this past season, with the Vegas Golden Knights winning 4-2 in the second round. It was especially frustrating for The City of Champions, as their hockey team held a lead in all six games.

Reaching the promised land

So what will it take, for the Oilers to finally reach the promised land and reclaim the holy grail of hockey? Well, this is where Holland has to earn his money, and prove he can replicate some of the success he enjoyed in Detroit.

Certainly, the 67-year-old needs to take advantage of the fact he has two of the very best players in the game, in Connor McDavid and Leon Draisaitl. Of course, no matter how good they are, you must still surround them with the right talent.

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Even though Holland has done a good job of building the roster, there’s still work to be done, including strengthening the blue line and the bottom six. The problem is, this is compromised by a salary cap which is essentially non-existent at this point.

However, this is why you pay Holland the big bucks, to work through situations like this. And – fair or not — the financial situation is one of his own doing.

Ken Holland not focused on himself

The Vernon, British Columbia native spoke to the media on the first day of Oilers training camp. As you’d expect he was asked about his future, but he’s not worried about himself.

Instead, Holland’s main concern is helping the Oilers go all the way in 2023-24. As per EdmontonOilers.com, he said:

"“I want to win a Stanley Cup. I mean, everybody in that room wants to win it. That’s my focus. I’ve been fortunate to have been part of four teams that won a Stanley Cup. There’s nothing like it for the city, for the players, for the organization.”"

We wouldn’t go so far as to suggest Holland’s legacy is on the line. He’s already achieved more than most GM’s could ever dream of, to have his reputation tarnished per se.

Will Ken Holland go out a winner?

Regardless, the 1975 Toronto Maple Leafs draft pick still faces immense pressure to win it all in Edmonton. To not accomplish this with the de facto best player in the game today in McDavid, would undoubtedly make for bad optics.

Holland happily joked about his age, but still believes he’s the right man for the job. He said:

"“I’ve got a lot of juice, I’ve got a lot of energy. I’m very motivated. I’m excited to work with (new CEO) Jeff Jackson. We’ve got great ownership, we’ve got a passionate fan base. I think we’ve got a really good team, and I’m really excited for this season.”"

The reality is this is likely Holland’s last season as GM in Edmonton, whether he helps the Oilers win the Stanley Cup or not. The fanbase understandably hopes it’s the former, so he can leave riding the high of success rather than slinking out under the low of failure.