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Kevin Lowe in 2008, when he was the Edmonton Oilers' general manager.Ian Jackson/The Canadian Press

Throughout his 40-year involvement with professional hockey, one often-underappreciated trait has served Kevin Lowe as well as any other in his Hall-of-Fame career: an impeccable sense of timing.

It famously served him well as a player, from his 1979 selection as the first NHL draft pick of the Edmonton Oilers, joining Wayne Gretzky to help usher in the last of hockey’s true dynasties, to joining the New York Rangers in time to end their 54-year Stanley Cup drought. And it served him equally well in the front office, teaming with Gretzky again to assemble the roster that enabled Canada to capture a first Olympic men’s hockey gold in 50 years.

Now he’s hoping to bring that sense of timing to his newest gig, sitting on the board of directors of Play On! Canada. As the organizer of mass-participation street-hockey festivals across Canada, Play On! is returning after a two-year pandemic-related hiatus with eight city stops this summer.

Of particular interest to Lowe is the sixth stop on the tour, scheduled for Sept. 10 and 11 in the ICE District outside of Rogers Place, the current home of the Edmonton Oilers. With the team just eight wins away from capturing its first Stanley Cup since Lowe was one of the team’s alternate captains in 1990, the hope is that the event in the Albertan capital might even have a special guest of honour.

But as somebody who has been lucky enough to spend quality time with Stanley on six occasions over the years, he knows that summer is always the busiest time for hockey royalty.

“I’m not sure whether we could even do that or not,” said Lowe, who credits playing street hockey over the potholes of his native Quebec for helping his skill development as a youth. “I know that it has a tight schedule. So I’d have to try to … I won’t even go there. But yeah, it’d be nice to have.

“It’s a great event anyway, but let’s put it this way, any time the Stanley Cup is around, it’s amazing, the allure and the attraction that that thing has.”

Hockey’s greatest antique is currently the object of fancy for two of the sport’s current stars, with Edmonton’s Connor McDavid and his Colorado Avalanche rival Nathan MacKinnon – who both played in Play On! street hockey festivals growing up – leading their teams to within touching distance of the cherished chalice.

For Lowe, currently an alternate governor of the team’s parent, Oilers Entertainment Group, the final four of this year’s Stanley Cup playoffs, between Edmonton and Colorado in the West and the Tampa Bay Lightning and New York Rangers in the East, offers him a unique perspective.

“When I look at the two teams, I think there’s no reason why the Oilers can’t or shouldn’t advance,” he said before Thursday’s Game 2. “And then, you know, obviously if they get to the finals, and it’s kind of the same reaction.

“I mean, circuitously, it’d be really cool if it was Rangers-Oilers in the finals, because there’s seven of us who played on the last Oilers Cup as well as the last Ranger Cup. So that’d be, you know, pretty cool in itself, but I don’t want to [put] undue pressure on the team.”

Given the 32-year NHL championship drought in Edmonton, it’s probably safe to say that no one dressed in orange and blue will be complaining whichever opponent the team might end up facing. Given the 2-0 hole the Oilers find themselves in, just getting to the final for the first time since the heartbreaking seven-game loss to Carolina in 2006 – when Lowe was the team’s general manager – would be a major breakthrough.

Even if the season ends without a parade, however, Lowe is optimistic that the former City of Champions – the highway signs that advertised it as such were taken down in 2015 – can live up to its outdated moniker again.

“I think everyone’s confident enough that if they don’t win this year, they’ll be in a position to win in the years to come ... because their stars are still well before their prime,” he said.

For a guy who played the majority of his 15 years in an Oilers uniform alongside Mark Messier, Jari Kurri, Paul Coffey and Gretzky – Hall of Famers all – Lowe also says that the fans can take heart from the inner drive possessed by the likes of McDavid and Leon Draisaitl. Both have accumulated multiple individual awards, but that won’t be enough for either.

He says it reminds him of his former captain.

“What Wayne Gretzky told me years ago is that he had won a bunch of scoring championships and he was MVP and all these things,” Lowe said. “But he said that none of this is ever going to matter unless we win some Cups if you really want to cement your place in history.”

Though McDavid, Draisaitl and the rest of the Oilers were shut out in Game 2 – just the second time Edmonton has been shut out since head coach Jay Woodcroft was hired on Feb. 10 – the pair of former Hart Trophy winners are putting up points at a rate hardly seen since Gretzky and Mario Lemieux were in their primes.

It’s surprised Lowe, who thought he’d never see players averaging more than two points a game this late into the postseason.

“No, I really didn’t,” he said, “and really what is very cool for me and I think for hockey fans in general is even the mere fact that Alex Ovechkin is potentially threatening Wayne’s goal-scoring record is, I would have said, that’s never going to happen.”

But as much as the superstars are dominating the scoring race – with McDavid and Draisaitl one-two on 29 and 28 points, respectively – Lowe points to the transformation of the team’s blueline in recent years as key to the current playoff run. The arrival of Cody Ceci, Tyson Barrie and Duncan Keith, along with the maturation of Evan Bouchard, have all helped in the Oilers’ turnaround this season, with many providing key playoff goals along the way.

One of the lessons that Lowe learned as a player is you have to give players a chance to succeed, and he points to the departure of Coffey in 1987 as an opportunity for other defencemen to step up, with the team winning another two championships in the three seasons after the Hall-of-Fame blueliner departed.

“My point is, you just never know, given the opportunity, how players will perform,” he said. “The Oilers have exceeded I think everyone’s expectations to be in the semi-finals right now.”