Twenty-seven years after that defining, singular, magical night in a legendary temple of the sport, the old Montreal Forum, Hakan Loob, now 56, has decided to retire from hockey.
Over the past two decades, he's served as GM, president and, finally, sporting director of Färjestad, the club he grew up in.
His impact on the development of and contribution to the '89 Flames' Cup team remains immeasurable.
He's won wherever he's been, domestically or internationally, as a player or executive.
"Hey,'' Loob is teasing, long-distance from Sweden. "You got a job for me? I'm available in a few months."
When the slight but sturdy right winger arrived here in the fall of 1983, chosen 181st choice overall the Flames in the '81 NHL Entry Draft, he quickly became the greatest Swedish import since Abba or Ikea.
A dynamic, hugely underrated player. A natural leader. And, most memorably, simply an outstanding person.
Leaving six years later for family reasons, just as he'd promised - determined that his young son Henrik be brought up on home shores - Loob exited a Stanley Cup champion.
His value in Calgary over that span goes galaxies beyond the 429 points, 193 goals and all-star team selection.
"If life would've turned out a little different, maybe I'd have had regrets,'' he says now.
"But when you think about it, what a way to go. On top of the mountain.
"Then, after I got home, I played in years that coincided with an acceleration of development for our club (Färjestad).
"It's been a good life back home. I had great success. My family grew, then all of a sudden you're in management. So I never really had time to dwell on what might have been.
"I guess there was the odd time thinking back, wondering 'What kind of contract could I have signed, 28 years old, Stanley Cup, 50 goals, 100 points, blah, blah, blah …'
"That's human nature.
"But I've always said: Money has never been the major issue with me. I knew I was coming back to a situation, to a league, where people weren't throwing money around all over the place, driving the greatest cars, owning huge houses.
"You realize pretty quick you don't need that much money. If I'd gone for the wallet, I never, ever would've signed for Färjestad."
As a Cup winner and a national icon as the first (and still only) Swede to net 50 goals in an NHL season, when news leaked that Loob would definitively be decamping for home, offers flooded in.
One Swedish club in search of a title told Loob they'd sign the cheque, he could fill in the number, and they'd also buy his house in Karlstad for twice what it was worth.
"Unbelievable offer. But I'd already decided Färjestad was my team, where I began, and I was definitely going back there. I didn't think twice."
Rejoining his old club, he'd go on to win back-to-back Guldhjalmen awards, signifying Swedish hockey's MVP as selected by his fellow players, still holds franchise records for goals and points in a season and over a career and holds the league record for most total goals.
Three days after retiring as a player in 1996, he was elevated to the club's GM role.
Since then, he's been a part of six additional league titles.
Occasionally over the course of his executive career in Sweden, rumours would begin circulating that he might be in line for this post or that position within an NHL organization. Smart, determined and well known in North American circles, he always seemed a forward-thinking, ideal fit.
"It just never happened,'' Loob says. "Regret? You can't really regret something you've never been asked to do.
"I never thought I could go high in management anywhere in North America, but you know what - if I'd got a call asking if I'd work in an organization, maybe not at the top, but to learn the ropes, I probably would've said yes to that."
Prior to the opening of this current campaign, the Färjestad board was informed by Loob that the club's all-time greatest sportsman would be stepping away for good at its conclusion.
The official announcement was made Monday.
So what lies ahead?
"The last while, I've become so interested in the NHL again,'' Loob confesses. "I have all the channels. I watch as many games as I can.
"So I wouldn't mind being a Swedish colour commentator on those games.
"Do … games from a Swedish control room in Stockholm and get the chance to travel over there from time to time."
When the Flames and Tampa Bay Lightning collided in the 2004 Stanley Cup final, Loob had to turn down an offer to commentate due to prior commitments.
"I'd love an opportunity like that again. I'd really like to really get to know the teams, do research," Loob says.
"What I'll miss is being around the players, being able to reach out and offer advice, or criticize when I had to. I think I'm a fairly social guy, so the relations between people, that's what I'll miss.
"But hockey's been too big a part of my life. It'd be hard to say, well, let's go fishing or play golf or just travel all the time.
"That's not me."
And even now, as the close to a brilliant career draws ever nearer, Loob continues to glance back to May 25, 1989 as his crowning achievement.
"You could put all the other titles together,'' he repeats, "and it wouldn't be the Stanley Cup.
"We had such a great group of guys … Lanny, Nieuwy, Robs, Pep, Vernie, all of them. You go through so much together.
"I remember being in the dressing room in Montreal that night and a Swedish reporter coming in. We're all hyped up, you know, got the Stanley Cup caps on, celebrating, and he asked, in Swedish: 'Doesn't it feel like you're the best player in the world now?'
"And I said, you know, cocky as hell: 'That's what I am!'
"I knew it wasn't true, wasn't close, but that's how winning the Stanley Cup - especially doing it the way did, those years building the team, then beating the Oilers, then winning right in Montreal - makes you feel.
"The adrenalin. The euphoria.
"You feel … unbeatable.
"It's the greatest feeling imaginable. Always will be."