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Dave Feschuk: The headaches might just be beginning for Leafs president Brendan Shanahan

To begin, a prediction: There’ll come a day soon when Brendan Shanahan will look back wistfully on the era that ended in May 2018 and say to himself, “Yikes. Remember when life at the office was easy?”

Until this month, after all, Shanahan occupied one of the most attractive gigs in pro sports. As team president of his hometown Toronto Maple Leafs, he was getting plenty of credit for a recent competitive renaissance. And yet Shanahan was also gifted with layers of self-installed, headache-reducing insulation. GM Lou Lamoriello, the ultimate in self-driven, big-presence team runners, was taking care of most of the details. Head coach Mike Babcock did most of the public messaging. And the roster, young and up-and-coming, mostly satisfied even the oft-delusional expectations of the sport’s most rabid fan base. When things went well, it was all part of the Shana-plan. And when they didn’t — well, trust the Shana-plan. It was the best of times. But those times are over.

When 32-year-old Kyle Dubas was named the 17th general manager in club history Friday, Shanahan’s work life got a lot more complicated. Suddenly he’s not just the team president. He’s also the in-office referee.

There are NHL lifers, after all, who believe Dubas’s biggest impending challenge isn’t negotiating contracts for Auston Matthews et al, nor plugging the gaping holes at centre and right defence. Dubas’s biggest impending challenge is managing Babcock. It’s expected Shanahan will soon enough find himself mediating disputes between the newly installed GM and the 55-year-old coach. Though born decades apart, the GM and coach share in common an ageless self-assurance and occasionally disparate views of the definition of a good-looking lineup.

Said one NHL source, imagining the outcome of the interplay: “(Babcock) is going to run roughshod over Dubas.”

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That might be an exaggeration for effect. But it’s not a stretch to suggest the Dubas-Babcock relationship could require a complicated bit of management from Shanahan. Just three years into an eight-year deal that pays an annual average salary of $ 6.25 million, Babcock isn’t some disposable coach, even if he has lost seven of his past eight playoff series. So it’s far from a coincidence that Shanahan gave Dubas a five-year contract, matching the remaining term on Babcock’s deal. Babcock, one source said, occasionally lorded his deal over Lamoriello, who was on a three-year term as GM.

Perhaps that’s part of the reason why even the 75-year-old Lamoriello, with his controlling tendencies, was occasionally swayed by Babcock’s persistent lobbying for roster changes. The 2016 free-agent signing of Matt Martin was in part a product of the coach’s ceaseless insistences, according to multiple league sources. Now it’s up to Dubas to figure out what to do with Martin, who can’t get into a game despite two years pending at a cap hit of $ 2.5 million a season. Still, if not for Lamoriello’s hockey-godfather steadfastness, it’s assumed Babcock would have attempted to exert even more control.

None of which is to say Dubas isn’t equipped to push back. The NHL is overdue for fresh blood in the executive ranks. And Dubas is as much a rink rat as anyone, having begun working for the Sault Ste. Marie Greyhounds at age 11 before climbing the ladder to scout at 17 and GM at 25.

Still, there are some around the league reading Dubas’s ascension as Shanahan wanting too badly for a protege to succeed despite red flags. Toronto’s succession plan, in theory, made sense. Hire Dubas. Bring in Lamoriello to mentor Dubas. Elevate Dubas. But unless “mentor” is a synonym for “marginalize,” a key step in Dubas’s development was essentially skipped. Running the AHL Marlies, Dubas’s Lamoriello-imposed gig before this one, isn’t exactly ideal training for running the Leafs. But being Lou’s right hand wasn’t an option. Assistant GM Mark Hunter got closer to Lamoriello than Dubas. But Hunter fell short in his push for GM and has not responded to requests for comment.

You can make a case the Leafs are repeating a mistake of their not-so-distant past by hiring a 30-something rookie GM. Former Maple Leaf Sports and Entertainment CEO Richard Peddie appointed a 36-year-old named John Ferguson Jr. in 2003 and lived to regret it.

“Yeah, (Toronto) is not a great place to start,” Peddie said, speaking over the phone this week.

Peddie, who cited the crushing weight of expectation as the No. 1 impediment to success in Leafland, seemed at least slightly amused to see history repeating itself. But the ex-CEO pointed out key differences. For one, Peddie figured it’s significant that Dubas is an internal hire (as opposed to Ferguson, who came from away).

“If they did go outside, it would cause serious issues inside,” Peddie said.

For another: “Ferguson never had a Shanahan.”

Indeed, while Peddie had hoped Ferguson would benefit from the worldly mentorship of Pat Quinn, the Leafs coach, that relationship never developed. Quinn, it turned out, harboured hard feelings about being stripped of the GM’s gig to make way for Ferguson. How was a CEO to know?

In any event, as Peddie can attest, those coach-GM conflicts were counterproductive, and evidently murder on the on-ice record. Not long after Ferguson arrived, the Leafs missed the playoffs 10 years out of 11.

Today’s Leafs are positioned far better than they were upon Ferguson’s arrival. So maybe it all works out. Maybe Hunter’s feelings won’t matter. Maybe Shanahan will be proven right and Dubas will figure out ingenious ways to placate Babcock’s ego. Those are maybes. What we can say with more certainty is that it probably won’t be long until the man behind the Shana-plan finds himself pining for the Shana-past. The team president’s job just got harder.

TORONTO STAR