Jay Woodcroft at risk if Oilers don’t win Stanley Cup in 2023-24

It’s not officially now or never for Jay Woodcroft, but his job as Oilers head coach will be on shaky ground if he doesn’t win the Stanley Cup this season.

When Jay Woodcroft replaced Dave Tippett as interim head coach in early February of 2022, the Oilers were in a desperate situation. On a dismal run of 7-13-3, they were five points out of the second wild card spot in the Western Conference.

What followed was quite simply inspiring, as Woodcroft galvanized the team. The Oilers went 26-9-3 over the remainder of the regular season, to secure second place in the Pacific Division.

In the playoffs, the Oilers advanced to the Western Conference final for the first time since 2005-06. And even though they were swept by the eventual Stanley Cup champion Avalanche, the future looked promising.

As a result, Woodcroft was rewarded with a three-year deal. However, with increasingly high expectations in Edmonton, his job security is arguably already looking uncertain.

Is Jay Woodcroft REALLY on uneven ground?

In some respects, this claim admittedly seems ludicrous. After all, the 47-year-old continued to get a lot right during his first full season in charge of the Oilers.

This included the team leading the NHL in goals scored. They also had the best power-play percentage in history, since the league started recorded this particular statistic in 1977.

The Oilers finished just two points off first place in the Western Conference, with their first 50-win regular season since 1986-87. However, they ultimately lost in the second round to the Golden Knights, who like the Avalanche a year earlier went on the win the Stanley Cup.

This led to Woodcroft receiving a lot of criticism, including looking out of his depth at key moments in the playoffs. As a result, his second full season in charge of the Oilers is a crucial one.

The Oilers have a talented roster; in fact one which is projected to be even better overall than last season. This is due to factors such as the addition of Connor Brown, a full season (hopefully) of Mattias Ekholm, Evander Kane fully recovered from injury and Jack Campbell looking more like his old self during preseason.

The best of the best

Of course, it also helps that the Oilers have discovered the cheat code in hockey. They have both the best player in the game and one who is arguably the second-best.

With a generational talent such as Connor McDavid alongside someone of Leon Draisaitl’s stature, Woodcroft doesn’t really have many (any) excuses not to win it all. Adding to the pressure, the Oilers only have two guaranteed seasons left of the duo, with Draisaitl set to become an unrestricted free agent at the conclusion of the 2024-25 campaign.

Of course we appreciate Hockey is a team game which requires everyone to do their part, combining trust, hard work and talent. In addition, luck can often play a role in the outcome of games, series and seasons.

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Regardless, any head coach would be salivating at the thought of being in charge of the Oilers roster. Heck, they probably still would be even if it was just McDavid and Draisaitl with sacks of potatoes as the rest of their teammates, but you get the idea.

The point is, Woodcroft is in an extremely fortunate position, with everything setup for him to succeed. He would become the toast of Edmonton and forever remembered in the annals of Oilers history, if he can help them win their first Stanley Cup since 1990.

However, if the Toronto native fails to do so this season, the pressure and criticism will only become more intense. And if he’s not careful, he might not even get to stick around to complete the final year of his contract.

It’s not now or never per se for Woodcroft, at least not as things stand. However, his coaching in the coming months will go a long way towards determining his future in Edmonton.