When Brendan Shanahan announced the hiring of 28-year-old Kyle Dubas as Toronto’s assistant general manager on Tuesday, it was a rare moment in recent sports history.

When was the last time, after all, that “Maple Leafs” and “progressive” could be used in the same sentence?

The struggling NHLers, out of the playoffs eight of the past nine seasons, have lately carved out a reputation as clueless heirs to one of the game’s richest legacies. Armed with more money than brains, they’ve been living luxuriously off the avails of a long-ago glory they’ve done little to enhance.

But adding Dubas to the executive team marks a moment of convention-shaking self-realization. Dubas, who’s been making a name as the youngest general manager in the Ontario Hockey League the past few years, is a rare combination. Along with being a numbers-savvy whiz kid with an affinity for the advanced analytics hockey has been slow to embrace, he’s also got an impressive résumé that includes stints as a snowbank-scaling junior scout and a player agent.

On Tuesday, Shanahan talked about how there are members of the organization who are still “afraid” of giving credence to statistical measures beyond the traditional tallies of goals and assists and plus-minus (hello, head coach Randy Carlyle). Dubas, hailed by Shanahan as a great compiler and communicator of such information, is expected to help change that.

Said Shanahan in praise of Dubas: “He’s not tied to any old ideas.”

In a sport in which ex-playing greats like Shanahan so often surround themselves with former teammates to engage in like-minded group think, Shanahan, 45, expressed his desire to build a front office that challenges his preconceptions. To that end, the club announced that executives Dave Poulin, 55, and Claude Loiselle, 51 — both ex-players who’d expressed their suspicion about the value of Moneyball-style advanced statistics — had been fired.

In some ways, it was a status-quo move in Leafland. Tuesday’s story wasn’t about star players winning Stanley Cups — it was about two guys in ties. Shanahan and Dubas now qualify as the faces of the franchise, just like Brian Burke before them.

And as for the collection of athletes who wear the uniform and were among the NHL’s worst teams as measured by most of the prevailing analytical measures?

“We’re working on it,” Shanahan said quietly.

The move could be interpreted as a sign of ongoing dysfunction. Dave Nonis remains GM, but Shanahan clearly pulled the trigger on Dubas. Now Nonis will have a boss (in Shanahan) and a right-hand man (in Dubas) with zero experience running an NHL club; he’ll essentially be training them both.

If he’s an ambitious new-school operator, Dubas, a native of Sault Ste. Marie, Ont., is from an old-time hockey family. His grandfather, Walter, coached the Greyhounds in the 1960s, and Kyle began his apprenticeship at the rink as the Greyhounds’ locker room attendant. By age 20 he was the youngest player agent to be certified by the National Hockey League Players’ Association. Three years ago, at age 25, he was hand-picked by the Greyhounds to run their hockey operation to great results. He made it clear he’s not some attached-to-the-laptop computer geek. But he acknowledged that statistics played “a big part” in his methodology for building his team.

“I think every organization, rightly or wrongly, changes every day,” Dubas said. “I think everything changes always, even if that doesn’t look like the case. If you’re not changing, everything around you is. Thus, you’re going to change and in not a great way.”

Hockey’s executive ranks are an unapologetic old boys’ club — the approximate average age of the NHL’s 30 general managers is 54. Dubas, who won’t be 29 until November, amounts to a young boy, indeed. But he has an eye on the corner suite.

“I still have it written down that one of my goals was to become the youngest general manager in the history of the NHL,” he was quoted as saying earlier this year.

Dubas, if that’s the goal, is in a race against time and against Gord Stellick, who became the youngest GM in NHL history in April of 1988, this when he took over the title for the Maple Leafs about a month shy of his 31st birthday. If you do the math, Dubas has about two years and a few months to steal away Stellick’s title.

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Stellick, informed of Dubas’ stated intention, laughed over a phone connection on Monday. Now a broadcaster with Sportsnet, he joked about the prospect of knocking Dubas down a peg.

“Now I’m going to have to be critical of him,” Stellick said. “That’s my claim to fame, but he’s welcome to it. My other claim to fame is, 16 months after I got the job I was the youngest ex-general manager in the history of the NHL.”

Yuks aside, Stellick, a keen keeper of the club’s history, concurred when it was pointed out that Tuesday was a landmark moment. Asked to name the last time the Leafs were synonymous with cutting-edge thinking, Stellick thought for a moment. He had to go back four decades or so to pinpoint the era: it was the late 1970s, when head coach Roger Neilson pioneered the use of video analysis and other then-unconventional techniques and was shortly thereafter run out of town.

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