Have the Oilers done enough to get Connor McDavid and Leon Draisaitl a Stanley Cup?

DALLAS — Everything about Dylan Holloway and Darnell Nurse sitting next to each other on an elevated dais at the Western Conference finals said quite a bit before either one of them answered a single question.

Between them, they represent so much of what the Edmonton Oilers have done to build around their generational superstars, Leon Draisaitl and Connor McDavid.

It’s important to have homegrown talent in today’s NHL, and the Oilers have that. They selected Nurse with the No. 7 pick in 2013 — a year before Draisaitl and two years before McDavid — which shows how long the Oilers have been trying to build through the draft. Holloway, who went 14th in 2020, is a more recent example of Edmonton remaining committed to that approach while simultaneously trying to win in the present.

“It’s cool to come in to a team with such phenomenal players,” Holloway said. “Darnell, Leo, Connor. I want to learn from those guys. They kind of paved the way here. Our team’s this good right now because of them.”

But while nine of the players in the Oilers’ Game 1 lineup were drafted and developed by the franchise, they had to build the rest of the team with intent. They acquired Warren Foegele and Zach Hyman because they needed forwards who could forecheck and score. They added Cody Ceci, Mattias Ekholm and Brett Kulak because they needed to strengthen a defense that was in a consistent state of flux.

The natural inclination could be that having superstars who have yet to hit 30, such as Draisaitl and McDavid, should guarantee a title at some point. But there are no guarantees in the Stanley Cup playoffs.

The Tampa Bay Lightning won consecutive Stanley Cups because they hit on first-rounders Victor Hedman, Steven Stamkos and Andrei Vasilevskiy while striking it rich with later-round picks Nikita Kucherov and Brayden Point. The Colorado Avalanche won their title because they were able to build around first-round picks Gabriel Landeskog, Nathan MacKinnon, Cale Makar and Mikko Rantanen.

Other teams, such as the Toronto Maple Leafs, show how building around a core of stars can come with many challenges. Despite having Auston Matthews and Mitch Marner, the Leafs have been beyond the first round only once since 2016, and there is no guarantee they’re going to win a championship with their current core.

Somewhere in the middle are the Oilers.

Since McDavid and Draisaitl first played together in 2015-16, winning the Stanley Cup has been the expectation. That only intensified once Draisaitl, who was drafted third in 2014, exploded for 50 goals and 105 points in his fourth season. His surge showed the Oilers truly had a pair of generational talents, and not just one in McDavid.

The Oilers have reached the postseason in five consecutive seasons. Altogether, they’ve missed the playoffs only twice in the McDavid-Draisaitl era. Until recently, the biggest highlight of those postseason runs came in 2022, when the Oilers reached the Western Conference finals for the first time since 2006.

If reaching the conference final in 2022 was a lesson, what they’ve done this year could determine if they’re ready to pass the final test by winning that elusive Stanley Cup.

But if they fall short, they may be a step closer toward being the latest cautionary tale of a franchise that built one of the most talented rosters of its generation and failed to win a championship.

“The organization as a whole, especially from when we first got here, has grown and grown,” Nurse said. ” At some points, when you first got here, it was like, ‘Are we ever going to even play in the playoffs?’ And now over the last few years, being a team that’s competing at this time of year is just a testament to ownership and management of where they wanted this team to grow and get to.”

The conversation about how this championship-caliber team was built starts with Oilers general manager Ken Holland bringing up two names from the team’s not-so-distant past.

The 2019-20 season was Holland’s first with the Oilers. The Oilers had several young players, with nine who were drafted by the franchise appearing in more than 20 games during that campaign. The tesm included Oscar Klefbom and Adam Larsson, who arrived in the Taylor Hall trade with the New Jersey Devils. But as Holland quickly noted, the departures of those two defensemen were the first metaphorical dominos to fall when it came to making the necessary adjustments to keep the Oilers competitive.

“Klefbom’s career was over because of his shoulder, and Adam Larsson, for personal reasons, made a decision that he didn’t want to be in Edmonton anymore,” Holland recalled. “Those are two massive pieces to try to replace. You just peck away.”

Draisaitl, McDavid, Nurse and Ryan Nugent-Hopkins are the only holdovers from that 2019-20 roster. Sam Gagner, who was drafted by the Oilers in 2007, played 36 games that season in his second stint with the club before he was traded to the Detroit Red Wings. Gagner returned for a third tour this season.

So how did Holland and his staff build out the roster? They constructed their current top defensive pairing by using the team’s 2018 first-round draft pick on Evan Bouchard, and then trading for Mattias Ekholm in 2023. It was a deal that saw them part with prospect forward Reid Schafer along with a 2023 first-round pick, a 2024 fourth-round pick and blueliner Tyson Barrie.

Holland’s 34 years with the Detroit Red Wings as an amateur scouting director, assistant GM and GM allowed him to learn something vital from former Wings GM Jim Devellano and coach Scotty Bowman: the importance of having depth players who can check, kill penalties and be trusted to play on either special teams.

“These are all the things that over 82 games are important, but over seven games are really important,” Holland said. “One miscue can change a game and change a series.”

Between Edmonton’s amateur and professional scouting staffs, Holland & Co. were able to identify the set of current NHL players who could fill those needs.

The Oilers’ professional scouting staff identified proven players who could address key needs for the club, such as Cody Ceci, Evander Kane, Brett Kulak, Derek Ryan, Foegele and Hyman, among others.

“I’ve been pretty fortunate throughout my whole career to make the playoffs, and there are some guys who’ve played a lot of games and not made the playoffs,” said Foegele, who arrived via trade in 2021. “It’s understanding that you don’t always get this opportunity. Obviously, the moves that Kenny has made — you understand what’s at stake and that everyone’s here to win.”

The prospects who became full-time roster players — such as Vincent Desharnais, Ryan McLeod, Stuart Skinner and Bouchard — were already in the system when Holland arrived, while Holloway was a pick made during Holland’s tenure.

“I think since being drafted and coming in here, they’ve kind of wanted to engrave a winning mindset,” Bouchard said. “They’ve had a lot of years prior when they didn’t have success. I think the guys here have learned from that, have built from that. They want guys coming in to know that this is a winning organization.”

As with many teams, the trick is finding the balance of using picks to build their system while knowing when to trade them to gain a useful veteran to help win right now.

The Oilers drafted 18 players in Holland’s first three years. Since then, they’ve traded away more than 20 picks and have drafted only seven players.

For example, the Ekholm trade means they don’t have Schaefer, their first-round pick in 2022, along with their 2023 first-rounder (which the Predators used to select defenseman Tanner Molendyk). They also don’t have their 2024 first-round pick because it was used in the three-team trade that brought in Sam Carrick and Adam Henrique at the trade deadline.

Past Oiler trades resulted in other teams cashing in well: The Minnesota Wild landed star defenseman Brock Faber, and the Montreal Canadiens secured defenseman Lane Hutson.

“Some have worked, some don’t … so we’ve traded away lots of futures looking at ‘this is the window,'” Holland said. “So what’s the window? You look at Connor, Leon, Darnell, Ryan. The players that were here, these are their prime years and trying to build a supporting team around them that can make us better.”

Holland said the Oilers felt good about their team. But their 2-9-1 start to this season led to the firing of coach Jay Woodcroft, who was replaced by Kris Knoblauch. The work done by Knoblauch and his staff — which includes Hall of Fame defenseman Paul Coffey — saw the Oilers go from near the bottom of the NHL standings to second in the Pacific Division by finishing 46-18-5 in their final 69 games.

That gave the Oilers the best record in the NHL since Nov. 12, 2023, when they announced they hired Knoblauch. Winning games, however, is only part of the equation. The Oilers returned to being the sort of prolific team that was averaging 3.72 goals per game, with a power play that was operating at 26.9% under Knoblauch.

They also found a way to establish a connection between their defensive structure and goaltending that hadn’t consistently been there in years past. The Oilers allowed 2.68 goals per game after Knoblauch took over, which was the fifth fewest in the NHL. Their penalty kill had a 81.7% success rate, good for seventh, while the 28 shots per game they allowed was also fifth fewest in the league.

“Everyone has had different roads to get to what our team looks like today,” Skinner said. “I think just combining all that experience and we’ve been able to grow with each other this season as well. Looking back on it, we’ve been through a lot obviously as a group. I think being able to go through what we have had to go through has brought us as a team a lot closer and we have a solid brotherhood now.”

All of their success led to a number of questions, the most significant being: Can the Oilers’ translate their regular-season success under Knoblauch to playoff success?

Beating the Los Angeles Kings in five games in the first round while fending off elimination twice to beat the Vancouver Canucks in the second round has helped answer that question. Holland said the key is having that mix of core players starting to hit their prime, with young players carving out their place alongside established veterans.

“But we also know we are in the final four, and these are the four teams that have performed the best to get to this point,” Holland said. “You’re playing the best teams in the world now. One’s going to advance, and one’s going to get shuffled to the sideline.”

The manner in which the Oilers won Game 1 of the Western Conference finals was emblematic of how they’ve tried to build a team around McDavid and Draisaitl.

Contrarians will point out that Draisaitl still scored the Oilers’ first goal, and McDavid scored the winning goal in double overtime. Those who have closely watched the Oilers will point out that the Game 1 win was a group effort.

Edmonton’s current setup meant it could rely upon a penalty kill led by Desharnais, Ekholm, Nugent-Hopkins and Ryan, among others, to blank Dallas on five attempts. Their most notable kill came just 17 seconds into overtime, when McDavid was assessed a high-sticking double minor. The Oilers’ short-handed unit took away time and space en route to running its streak of consecutive kills to 21 entering Game 3.

“I think it’s just about confidence,” said McLeod, who is part of the Oilers’ PK setup. “We’ve been tweaking it all year and we’ve found something that’s been working. It’s confidence and that everyone’s in the right spots and being aggressive, and it’s been working.”

While Bouchard and Ekholm played more than 31 minutes in Game 1, the Oilers have been able to find a balance with their six defensemen. They all played more than 20 minutes that contest, while the Stars have largely relied on five defensemen this postseason.

Prior to Game 6 against the Canucks, Skinner had a 4.63 goals-against average and a .790 save percentage this postseason. Since then, he has a 1.64 GAA and a .918 save percentage in four starts.

This postseason also shows how the Oilers are more comfortable playing in one-goal games. They’ve won six out of their 10 one-goal games, with nine of their past 11 games being decided by a single goal.

Contrast that to the prior two years, which saw the Oilers go a combined 3-6 in one-goal games. Last postseason, they had just one one-goal game in their second-round series against the Golden Knights, while having a lone one-goal game versus the Avs in the conference finals in 2022.

“You’ve got to win tight games,” McDavid said following Game 1. “We’re down to the final four teams and you don’t get to the final four without being a great team. All four teams are solid. Dallas is a great team and it’s going to be tight hockey and we’re comfortable in these games. We’re comfortable in this environment, and I thought we did a great job truthfully all game.”

Winning Game 1 of the Western Conference finals has technically made this the most successful campaign in the McDavid-Draisaitl era, considering that they were swept the last time they were at this stage in 2022.

They’re seven victories away from winning the organization’s first Stanley Cup since 1990. Only five players on the current roster were alive when Mark Messier raised the Cup that spring. In fact, Ekholm was born on the exact day when the Oilers won their last Cup which was May 24, 1990.

Capturing the Western Conference crown and then winning the Stanley Cup would bring an end to all the questions surrounding the Oilers’ strategy in building around Draisaitl and McDavid. From there, the discussion would shift to whether they could win at least one more.

Falling short of the Cup would lead to more questions in what could be an offseason of change.

The Oilers have a 10-player unrestricted free agent class. It’s a group that includes Foegele, Henrique and Desharnais. Decisions will need to be made about how to strengthen the Oilers with what CapFriendly projects to be less than $10 million in cap space.

Even that comes with questions about who would be the one charged with improving the roster; Holland is in the last year of his contract.

And if all of that isn’t enough, Draisaitl will be entering the final season of his contract, too. Whatever he decides to do will have a significant ripple effect throughout the NHL.

“Once you’ve built your team, every year is the year,” Holland said. “You’ve always got to have a look to the future. Then when the year’s over, and you haven’t won the Stanley Cup, you’re gutted. There’s an empty hole in the pit of your stomach. That’s where you have to take the summer whether you’re a player, a coach or manager and you’ve got to regroup and rebuild and play your way back into another opportunity. I think that’s certainly what we’ve done.”