State of the Stanley Cup drought: How close are Oilers to winning with McDavid?

The Edmonton Oilers are hoping Connor McDavid can help them win their first title since Mark Messier was their leading scorer.

This is Part 3 of a 10-part series examining the longest Stanley Cup droughts in the NHL, and how close teams are to breaking through for their first championship in decades — or ever.

Previous articles: Senators, Sharks

There's no doubt that the Edmonton Oilers have iced some of the best teams in NHL history. Unfortunately for the storied franchise, it hasn't claimed a great deal of success since its last title in 1989-90.

Since that season, Edmonton's point percentage (.495) ranks 28th in the league — and only two teams have more total losses than the 1,291 the Oilers have accumulated. The period between 2006-07 and 2018-19 was particularly grim, as the club made just one playoff appearance, bowing out in the second round.

Amongst the trials and tribulations, there have been a few notable highlights and the emergence of Connor McDavid as the NHL's best player — and Leon Draisaitl as a true superstar — has given the team a solid chance of bringing the Cup back to Edmonton.

Here's a look at the state of Edmonton's Stanley Cup drought:

Connor McDavid can keep the Oilers' championship window open as long as he's in Edmonton. (Ric Tapia/Icon Sportswire via Getty Images)
Connor McDavid can keep the Oilers' championship window open as long as he's in Edmonton. (Ric Tapia/Icon Sportswire via Getty Images)

How long has it been?

The Oilers have not won the Stanley Cup in 32 seasons.

How close have the Oilers come?

Although Edmonton's overall record over the course of their drought is rough, the Oilers have come closer to winning a championship that many other teams that have been waiting 30-plus years for a Cup.

The headliner among the team's close calls was 2005-06, when Edmonton lost to the Carolina Hurricanes in a seven-game Stanley Cup Final series. The Oilers crawled back from a 3-1 deficit to even things up, but ultimately couldn't close it out.

Perhaps the greatest what-if associated with the Oilers-Hurricanes battle is whether Edmonton could've prevailed if Dwayne Roloson hadn't gotten injured in Game 1. The veteran netminder had been on a roll during the postseason and Edmonton was forced to turn to Jussi Markkanen, who posted a .880 save percentage during the regular season and managed a middling .905 in the series.

The absence of Dwayne Roloson may have swung the 2005-06 Stanley Cup Final. (Andre Ringuette/NHLI via Getty Images)
The absence of Dwayne Roloson may have swung the 2005-06 Stanley Cup Final. (Andre Ringuette/NHLI via Getty Images)

The Oilers outshot Carolina 200-163 over seven games, and better goaltending may have put them over the top. Both goals Markkanen gave up in Game 7 were slap shots from defencemen who'd never topped seven markers in a season, and it's not easy to envision Roloson stopping one or both.

Following 2005-06, superstar defenceman Chris Pronger requested a trade, the team's top three forwards — Aleš Hemsky, Shawn Horcoff, and Ryan Smyth — took a step back, and the championship window closed.

Edmonton reached the Conference finals on three other occasions during its drought, but it didn't come close to playing for the Cup on any of those occasions. In those three series, the Oilers went a combined 1-12, with their only win coming against a Minnesota North Stars squad on a magical run despite going 27-39-41 during the regular season.

Outside of a lopsided Game 2 win for Edmonton, the heavy underdogs outscored the defending champs 18-6.

During the McDavid era, the Oilers have been thought to have teams capable of winning the Cup at times, but without a win past the second round, it'd be hard to say they've been knocking on the door.

How does Edmonton's championship prognosis look now?

Edmonton will enter the 2023-24 season as one of the Stanley Cup favourites, as McDavid and Draisaitl can be counted on to drive one of the NHL's best offences, and the blue line looks stronger than it did at the outset of 2022-23 thanks to last season's addition of Mattias Ekholm.

A relatively inflexible cap sheet made it difficult for the Oilers to make big moves during the offseason, but bringing versatile winger Connor Brown aboard could pay dividends if he stays healthy.

While the supporting cast around McDavid and Draisaitl has been shaky at times over the past few years, it looks solid now. The biggest question is in net, where Stuart Skinner is unproven with just 61 NHL starts under his belt and Jack Campbell has been well below-average since midway through the 2021-22 season.

As long as McDavid and Draisaitl are on the Oilers this team has a legitimate shot to win it all, and they've assembled a quality squad ahead of the 2023-24 campaign. In the short term, Edmonton looks like a real threat to end their Cup drought.

The future is a touch murky for this club. Drasaitl is only under contract for two more seasons and he's due a gargantuan raise on his current $8.5 million cap hit. The McDavid clock is ticking as well, as he's signed for three more years.

If Edmonton is unable to extend one or both of its superstars, then their championship window could evaporate in short order. Signing both to the kind of deals they'll command would likely create some more cap difficulties in the years to come.

Fitting two of the best players in the NHL under the cap is a worry most teams would love to have, but even though both McDavid and Draisaitl are relatively young, their contract situations makes it difficult to project that this team is sure to compete deep into the 2020s.

That may well be the case, but there are more unknowns to contend with here than there are with other teams that have their young core locked up — like the New Jersey Devils, for instance.

Because Edmonton has been relatively successful during McDavid's tenure, the team hasn't had many high picks and its prospect pool is considered to be below-average. There's no obvious home-grown stars that look like a next wave for this franchise, even if guys like Dylan Holloway and Philip Broberg could be on the brink of playing bigger roles.

The Oilers are locked into what they've got now. That's a fine place to be, but it's possible that Edmonton's best chance to break through for the foreseeable future is right now.