How Kyle Dubas can channel Masai Ujiri to improve Maple Leafs this summer

TORONTO — This will be a difficult off-season to message, let alone manage.

Mere hours before puck drop on Montreal’s second-round series in Winnipeg, Kyle Dubas and Brendan Shanahan will log in to Zoom late this afternoon and attempt to explain why the Toronto Maple Leafs aren’t playing there instead.

We should also expect a few hints of what’s to come, as much as that can be known so soon after a faint-hearted Game 7 showing against the Canadiens.

Management has been left in a tough spot with the way a promising season came crashing down. It would be unwise for them to overreact to another first-round disappointment, as unseemly as it was, but facing a growing crisis of public confidence in the program they’ve built it’s not enough to come out and say, “We’re staying the course.”

Fans and media members don’t need to be as clear-headed as those steering the ship through a storm. Many will be demanding tangible change after a best-of-seven that turned partly on bad luck — starting with the freak accident that kept John Tavares from having any impact on the series and included an overtime period where Toronto registered the first 10 shots on goal and still lost.

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That’s raised not as an attempt to diminish Montreal’s victory, only to underscore how thin the potential range of outcomes is. Put another way: The Leafs just lost a series where they scored more total goals, took more shots and shot attempts, generated more scoring chances and saw their goaltender finish with the highest save percentage.

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Now there are only off-season games left to play, with an entry draft, expansion draft and free agency to navigate over the next eight weeks.

Those will come with some challenging decisions in Toronto, especially with Dubas into his fourth calendar year on the job and approaching his seven-year anniversary with the organization. He’s going to be making calls on trusted players that have been part of the franchise’s turnaround, rather than just the veterans he inherited from the Nonis/Burke era before it.

And he’s got some cards to play if he believes this group could benefit from a shakeup.

Dubas has close ties to the Toronto Raptors front office — where GM Bobby Webster is a contemporary and friend — and he had a behind-the-scenes view into the bold summer of 2018 where they fired NBA coach of the year Dwayne Casey and traded franchise icon DeMar DeRozan for Kawhi Leonard, ultimately paving the way for their 2019 championship.

Dubas has spoken in the past about admiring how tough the Raptors management group was. About how they stayed patient in the face of public criticism and believed in their operation enough to make major moves when required. During a January 2019 appearance with Webster at the Empire Club, he said: “Just watching the [Raptors] organization evolve, I’ve learned a lot from them.”

So how might the Leafs evolve before a return to the imposing Atlantic Division in the fall if he channels Masai Ujiri this summer?

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1. Everything starts with the Core Four.

Tavares, Auston Matthews, Mitch Marner and William Nylander were all signed to rich contracts under the assumption that those deals would become more manageable as the salary cap increased over time. But the pandemic has created a flat cap environment, with the ceiling likely to remain at or near $81.5-million for the duration of those deals.

What the Leafs need to determine is if they can reasonably build a contender each year while allocating nearly half of their available cap space to those four forwards. No matter where they fall on that fundamental question, they’ll also need to seek answers on why Matthews and Marner faded after delivering two of the best regular seasons in club history: Were they playing too much? Should they be deployed exclusively together on the same line? How significant was the mental block of past playoff losses on this performance?

Ultimately, it’s inconceivable to imagine any scenario where either gets traded — having two elite players is what separates the Leafs from basically 90 per cent of their opponents — and with Tavares holding a no-trade clause and serving as team captain he’ll remain in the fold, too.

That leaves the question of Nylander, their most productive performer in the series with Montreal. He’s delivering value on a $6.9-million cap hit but might be deemed a luxury item given the cap challenges at play. He was the team’s first draft selection after Shanahan became president and while parting with him wouldn’t be easy, it can’t be ruled out entirely because it would allow them to build out a bigger middle class among their forward group.

2. Next on the sentimental scale are Zach Hyman and Morgan Rielly, two heart-and-soul players that would be strong candidates to be lifetime Leafs in a world without a salary cap.

Hyman might simply have priced his way out of his hometown by scoring at a 28-goal pace across the last three seasons. He was a savvy Dubas acquisition in 2015 and became a core part of the team, but is in position to command a contract in the $6-million range as an unrestricted free agent.

While it’s not a foregone conclusion he’s leaving Toronto, it’ll probably take an adjoining move to keep him on a hometown discount. And entering his age 29 season, this looms as a big business decision for Hyman, too.

The decision on Rielly isn’t quite so pressing since he’s under contract for another year.

However, the Leafs are permitted to sign him to an extension starting July 28, and if they’re not comfortable giving him a significant raise on his current $5-million deal there’s a case for maximizing his value with a trade.

This would be akin to the Raptors move with DeRozan. Rielly is a highly valued member of the organization, a popular teammate in the dressing room and he delivered a strong performance in the Montreal series.

But he also saw some power-play minutes lost to Rasmus Sandin late in the season — Sandin has one year remaining on an entry-level contract — and would net a significant return in a trade.

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3. Revisit the coaching staff.

Sheldon Keefe was Mike Babcock’s hand-picked successor, delivered the best winning percentage through 100 games of any head coach in Leafs history and shares a long winning history with Dubas. The odds of him paying the price for the collapse against Montreal seem infinitesimally low, even if his own performance in the series invited scrutiny.

But it’s difficult to imagine his staff remaining intact after finding no answers for the struggling power play under first-year assistant Manny Malhotra. The Leafs were vastly improved defensively, which fell under the purview of assistant Dave Hakstol, but he’s a holdover from the Babcock era and could move on.

Veteran Paul MacLean just completed his first year as an eye-in-the-sky assistant who remained at home to observe the team from afar when it went on the road.