How years as an underdog, then a laughingstock, led the Oilers to this defining moment (2024)

SUNRISE, Fla. — The Connor McDavid-led Edmonton Oilers were always supposed to be here, one win away from a Stanley Cup championship.

That it’s taken this long to get back to this spot is another thing entirely, though.

“It’s been a heck of a ride,” veteran defenseman Darnell Nurse said. “I’ve enjoyed the highs, the lows — everything that’s come along with it. It’s allowed me to grow, not only as a player but as a person.”

It’s been nine years since McDavid was drafted. And it’s been twice that long since the 2006 Oilers came up a victory short of winning it all.

The journey has been a winding one for the franchise — full of stops, wrong turns and near-calamitous mishaps.

“It’s been a long road to get to this point,” McDavid said. “It’s been a lot of ups and downs. A lot of lessons along the way — a lot of lessons. But it takes a lot. It really does.”

The Oilers are now on the verge of perhaps the greatest story in NHL history as they try to complete a 3-0 series comeback over the Florida Panthers.

But, as the saying goes, Rome wasn’t built in a day. And in this case, it was built and rebuilt several agonizing times.

From the moment Wayne Gretzky was sold to the Los Angeles Kings in 1988, the Oilers transitioned into a farm team for the rest of the NHL. Even after winning the last of their five Stanley Cup titles — so far — without him in 1990, that decision indicated they couldn’t keep up with the big spenders around the league.

A new decade reinforced the notion that they would trade players they could no longer afford. Then the same thing would happen with the young players they had acquired in those trades. For instance, Doug Weight, the return in the Esa Tikkanen trade in 1993, became a star and the team’s captain but was eventually dealt to St. Louis when his value got too high.

The team was owned by a group of local business people just trying to make ends meet amid a low Canadian dollar. What eventually helped, for a time anyway, was the implementation of a salary cap to go along with a 24 percent rollback in player salaries after the 2004-05 lockout.

The Oilers didn’t have many commitments on their books and they acquired respected veterans Chris Pronger and Michael Peca ahead of the 2005-06 campaign.

“We wanted to put our money where our mouth was,” GM Kevin Lowe said.

Lowe felt Pronger took 15 or 20 games to get his footing. Peca struggled during the regular season, too. But the moves signified the Oilers were players around the league again. On the ice, the Oilers were inconsistent until the trade deadline. The reason was obvious.

“We’d outshoot teams 18-2 and be down 1-0 after the first period,” coach Craig MacTavish said.

“We’d all talk about it,” Lowe said. “If you have to ask the question, you probably know the answer. We needed a goalie.”

Minnesota Wild GM Doug Risebrough was up for dealing one of his two starting-caliber netminders, Dwayne Roloson or Manny Fernandez, and wanted a second-round pick. The Oilers targeted Roloson. Lowe jumped the market by offering a first-rounder ahead of the trade deadline.

Lowe also picked up defenseman Jaroslav Spacek and winger Sergei Samsonov. Roloson was the difference-maker.

The Oilers squeaked into the playoffs and played the top-seeded Detroit Red Wings, who finished 29 points ahead of them in the regular season.

“Nobody thought we could win,” said winger Fernando Pisani, who had 14 goals in the 2006 playoffs.

MacTavish felt there were large stretches, and full games even, where the Red Wings were the better team. It came down to Roloson outplaying counterpart Manny Legace.

“It was no contest,” MacTavish said.

The Oilers beat San Jose and Anaheim in the next two rounds to face the Carolina Hurricanes in the Stanley Cup Final.

Roloson sustained a series-ending knee injury in a Game 1 loss where the Oilers blew a three-goal lead. They trailed 3-1 in the series, but Pisani scored a short-handed breakaway goal in overtime of Game 5 and the Oilers demolished the Hurricanes 4-0 in Game 6.

However, MacTavish felt they came out flat in Game 7 and never recovered. They lost 3-1 in Raleigh, N.C.

“Sometimes the great story doesn’t end the way it’s supposed to,” captain Jason Smith said.

“It’s something that never leaves you,” Pisani said.

“I feel worse about it now than after the game,” MacTavish said. “It’s really stinging to this day that we didn’t win that game.”

MacTavish felt terrible for longtime Oilers like Smith, Ryan Smyth, Ethan Moreau and Shawn Horcoff who just missed out on the Cup after suffering through so much with the organization.

The familiar pain was about to return.

The Decade of Darkness began when Pronger’s trade demand was made public in the days following the Game 7 loss and Lowe acquiesced, moving the hulking blueliner and future Hall of Famerto the Anaheim Ducks. Spacek and Samsonov proved to be nothing more than rentals and signed elsewhere. The team started crumbling.

“You lose a guy like Pronger and that hurts,” Pisani said. “He was one of the best defensem*n in the league for a long time.”

Lowe said he wished he had never traded Pronger, who wanted out because of family reasons. He’s come to realize that stars of Pronger’s magnitude are vital to a team’s success.

“I would have done things a lot differently,” Lowe said. “I probably wouldn’t have traded him and just let him sit.”

The Oilers won just 32 games the next season and the turnover intensified. Smith, who had just matched Gretzky as the longest-serving captain in team history, was dealt to Philadelphia that summer.

“There were players, including myself, that didn’t have as good a year as we wanted to have,” said Smith, who was “disappointed and shocked” when he got the news he had been traded.

“I can honestly say we went out and played that next year as hard as we could every night. We just didn’t have success. We didn’t have the year we hoped after the run we had the year before.”

Lowe tried to augment the team in free agency to “stay in that 2006 mode” of being competitive enough to make playoff runs. He said he made substantial offers to Chris Drury, Scott Gomez and Daniel Briere — the three highest-profile players on the market in 2007. In some cases, he never even heard back from their representatives.

Edmonton wasn’t a desirable location, especially with the team losing, to some of the best players in the game.

So, Lowe went a different route that summer by signing restricted free agents Thomas Vanek and Dustin Penner to lucrative offer sheets. Buffalo matched Vanek’s offer, whereas Anaheim didn’t with Penner.

The next offseason, Lowe wanted to sign Marian Hossa and even made a pitch to pry Jaromir Jagr out of Russia. His successor, Steve Tambellini, had a deal in the works to acquire disgruntled winger Dany Heatley from Ottawa, but he wouldn’t waive his no-movement clause to come to Edmonton.

“We legitimately couldn’t get players here,” Lowe said.

The Oilers bottomed out with a 27-win season under Pat Quinn in 2009-10, which commenced a stretch of three straight seasons where they were awarded the No. 1 pick in the draft. Lowe said they tried to accumulate top prospects through the draft for a few years.

“It was tough to transition to the years that happened after (the Cup Final),” said Pisani, who spent his last NHL season with Chicago in 2010-11. “It was frustrating. You get so close. You hope to have another opportunity to achieve that.”

“There was no sense staying in the middle,” MacTavish said.

However, not all drafts are created equal.

The Oilers selected two solid players, Taylor Hall and Ryan Nugent-Hopkins, in consecutive years. The former won the 2018 Hart Trophy in New Jersey, and the latter has been a pillar of the franchise. However, neither is destined for the Hockey Hall of Fame.

The last of those three top picks, Nail Yakupov, has spent the last six seasons in the KHL. Yakupov headlined a weak draft class; the only player from the top five still in the NHL is No. 5 selection Morgan Rielly.

“The problem with that decision to follow the Pittsburgh-and-Chicago model is that you’ve got to draft (Sidney) Crosby or (Evgeni) Malkin or (Jonathan) Toews or (Patrick) Kane,” Lowe said. “Nuge is a good player. Taylor Hall is a good player. But they’re not superstars. They’re not the type of guys who can put you over the top. If you don’t get those (top) guys, you stay an average team at best.

“But it’s like planting a new crop. You’ve got to let it grow and see what it is. You don’t even know if you’re going up or going down for a few years.”

The Oilers drafted Darnell Nurse seventh in 2013. It turns out it wasn’t until they scored by selecting Leon Draisaitl at No. 3 in 2014 that they finally landed that franchise player. Draisaitl was the player MacTavish, now GM, badly wanted, though even he admits the decision to draft him over Sam Bennett — now with Florida — panned out better than expected.

“It’s hard to predict a guy who’s iconic like that,” MacTavish said. “The scouts were pretty firm about Leon over Bennett. He didn’t have the same skill set that Leon did.”

The ultimate fortune came when they won the 2015 draft lottery, giving them the right to draft McDavid, who had long been touted as the next generational star.

“The other (top picks) were good players, but they weren’t that animal that Connor is,” MacTavish said.

“Connor really helped,” Nugent-Hopkins said, laughing. “You get a guy like that, and Leo, and Nursey. You can really build a team around guys like that. We’ve gone from there.”

In 2017, McDavid’s second season, he won his first scoring title and helped the Oilers return to the playoffs. It was their first postseason appearance since the run to the Final in 2006.

But the Oilers, under GM Peter Chiarelli, were already in a tailspin of shortsighted moves. The Oilers needed help on defense, and he acquired the sturdy Adam Larsson the previous summer but dealt Hall straight up to do so. He also signed Milan Lucic to a gargantuan contract.

Chiarelli then sold low on winger Jordan Eberle after a subpar playoff performance. Lucic was a shell of the player they thought they were getting by his second season.

The Oilers missed the playoffs and got off to a slow start the following season, then coach Todd McLellan was fired.

Ken Hitchco*ck came in and steadied the ship for a bit. But the Oilers lost Oscar Klefbom and Kris Russell, two top-four defensem*n, in the same December game in Colorado due to injury. Hitchco*ck said he knew they were doomed then, even though a win improved them to 17-12-2.

“The team was rather limited,” Hitchco*ck said. “We just didn’t have the depth to remain competitive.

“We were scrambling.”

In a desperate attempt to save the season, Chiarelli soon acquired Brandon Manning and Alex Petrovic — both of whom barely played when the defense corps returned to full health. Chiarelli was fired in January of that season.

In May 2019, the Oilers hired Ken Holland out of Detroit as Chiarelli’s replacement — Keith Gretzky briefly held the interim duties — and he had a mess to clean up.

While Chiarreli’s drafts yielded current players Evan Bouchard, Stuart Skinner, Ryan McLeod and Vincent Desharnais, and he signed Draisaitl to what’s turned out to be a bargain contract, the roster Holland assumed was bereft of the depth needed to complement McDavid and Draisaitl.

With little cap space, Holland spent the offseason signing the likes of Riley Sheahan, Josh Archibald, Joakim Nygard, Gaetan Haas and Tomas Jurco to create what he called “tryouts” under new coach Dave Tippett.

“I wanted to sign lots of players and create competition,” Holland said.

It worked. The goal was to play meaningful games in March. The Oilers had a playoff spot nearly locked up when the league shut down on March 12 because of the pandemic.

A turning point toward what Holland termed “continuity” came in the 2021 offseason when he bought out James Neal — a player he took on to rid himself of Lucic’s buyout-proof contract — and put the savings toward signing Zach Hyman.

Holland felt the Oilers were too reliant on the rush and wanted to get better off the cycle, on the forecheck and in the blue paint. The scouts identified Hyman and Warren Foegele for those areas. Holland also replaced Klefbom, who had essentially been forced to retire because of a shoulder injury, with Duncan Keith and later Mattias Ekholm.

Holland has augmented the depth annually and overhauled the roster. To illustrate that, only McDavid, Draisaitl, Nugent-Hopkins and Nurse were regulars before Holland joined the organization. (Sam Gagner, a 2007 first-round pick, was traded by Holland before the 2020 deadline but returned this season for a third tour of duty and is now a black ace.)

It’s been a slow build — perhaps slower than some would have liked.

“I knew the team had a good core,” Holland said. “But, based on my time in Detroit, I understood the importance of depth. Those are key pieces, too. Every piece is hard to find.

“This team has always had Connor and Leon. We had to build around them.”

Holland is the first person to note that not all his moves have worked out. But the Oilers have made it to Game 7 of the Stanley Cup Final with a chance to complete a truly remarkable comeback.

“They’ve earned their way to a championship,” Hitchco*ck said.

It took a long time to get to this point. Nugent-Hopkins, the longest-tenured Oiler at 13 seasons, gets that more than anyone. He’s played for 10 coaches in Edmonton,including MacTavish as an interim in 2014-15.

“Most guys have to go through some hardships,” he said. “It’s not easy to just be on a good team every single season if you’re going to play a long career. I went through it my first few years, but I always believed that we had the core and could find a way out of it.”

Lowe and MacTavish are both confident in the Oilers’ chances on Monday — mainly because of the difference in quality between the 2024 outfit and the one they led.

“I don’t compare this year’s team to ’06 at all,” Lowe said. “This year’s team is a better team.

“We couldn’t score the way these Oilers can score.”

The one thing these Oilers can’t do is make the same mistake the previous group did in Game 7 of the Cup Final. It’s the one bit of guidance offered by MacTavish.

“Don’t assume that it’s just going to be Period 4 of Game 6,” MacTavish said. “They’re going to have to play their best game of the series to win.”

You can bet that advice isn’t being taken for granted given what it’s taken the organization and the veteran players to get here.

“We’ve had a few cracks at long playoff runs,” Nurse said. “But there’s been no satisfaction — and there’s no satisfaction now. There’s still one more to go.”

(Photo of Connor McDavid: Codie McLachlan / Getty Images)