Breaking down Brad Treliving's top priorities as Leafs GM

Brad Treliving was announced as the next general manager of the Toronto Maple Leafs on Wednesday and the 53-year-old is inheriting a team on the cusp of its boiling point.

Treliving, best known for his tenure as the Calgary Flames' general manager (2014-23), is now tasked with driving the NHL’s most visible team, where the expectations are not only to win now, but win several playoff rounds in order to appease seven consecutive years of stark disappointment.

Here’s a list of priorities for Treliving to get started on right away:

Re-establish trust with Auston Matthews and William Nylander, then sign them to extensions

Auston Matthews is eligible for a long-term extension on July 1 and reestablishing a strong relationship with the former Hart Trophy winner is Treliving’s top priority. Matthews is a top-six player in the NHL at minimum, he’s entering the apex of his career, and he has stated repeatedly that he wants to remain with the Maple Leafs. There’s no point in even building a franchise if you can’t secure a player of Matthews’ caliber to a contract that sees him enter his mid-30s.

“My intention is to be here,” Matthews said on May 15. “I think I've reciprocated that before, how much I enjoy playing here and what it means to me, the organization, my teammates and how much I just enjoy being here."

Matthews and former Maple Leafs general manager Kyle Dubas were very close — there’s only a 12-year age gap between the executive and superstar. This dynamic may change with Treliving, a 53-year-old who is the prototypical Hockey Man personified. It’s been reported that Matthews’ agent, Judd Moldaver, is on good terms with Treliving and this shouldn’t be a major impediment.

If Treliving wants to get his critics off his back, his first order of business needs to be a seven-year contract and upwards of $12 million annually for Matthews, who is not only one of the NHL’s premier scorers but now one of the NHL’s best defensive forwards as well.

Nylander also has one year remaining on his existing contract, which is one of the most team-friendly deals in the NHL, as he’s scheduled to earn $6.92 million for the 2023-24 season. If he’s on the roster as of July 1 — and barring a drastic move ahead of the NHL Draft in June, he absolutely should be — Nylander’s 10-team no-move clause will kick in. In an identical fashion to Matthews, Nylander clearly wants to remain with the Maple Leafs and told reporters matter-of-factly that he still has a year left on his current pact.

The 27-year-old is coming off a career season in which he scored 40 goals and 87 points while playing in all 82 regular-season games. He then registered just under a point per game in the playoffs, tallying four goals and 10 points in 11 contests.

Nylander is one of the best offensive weapons and individual drivers of play in the NHL and it would be a massive mistake to trade him for the sake of making a move. Treliving should understand this and needs to get to work on building strong relationships with two of the team’s core pillars.

Make a long-term decision on Sheldon Keefe

At the time of this filing, Sheldon Keefe is still the Maple Leafs’ head coach. Treliving will need to meet with Keefe immediately and assess whether the 42-year-old is still the person to lead the Maple Leafs into a breakthrough era of prosperity. Sportsnet’s Elliotte Friedman reported Treliving is open to keeping Keefe and Shanahan has offered a vote of confidence.

Shanahan previously told reporters on May 19 that Keefe’s fate would almost certainly be decided by the new general manager. Keefe’s contract is scheduled to expire at the end of the 2023-24 season and it’ll be compelling to see if the Shanahan-Treliving tandem view the incumbent as a stop-gap option, the bench boss of the next era, or an untenable choice going forward.

Keefe is an interesting prism to view the Maple Leafs as a whole. During his four seasons as head coach, he’s posted a .678 winning percentage in 267 games — the ninth-best percentage in NHL history, and that takes into account coaches who managed fewer than five contests. It’s a historically strong record. And yet Keefe’s .433 postseason winning percentage is what damns him. Can you make the argument that he’s maximized the strengths of a hyper-talented team when the Maple Leafs repeatedly crash into a wall in the spring?

It seems unlikely Treliving would bring back former Flames head coach Darryl Sutter, whose demeanour and tactics are in direct opposition with the ethos of the Maple Leafs’ superstar players. After a seemingly non-exhaustive search for Toronto’s next general manager, the Maple Leafs’ new management regime may be wise to cast a large net if Keefe isn’t returning.

Cautiously approach the idea of asking John Tavares to waive his no-trade clause

There’s a clear dilemma enveloping the Maple Leafs: in order to make the roster more flexible, they will have to trade one of their Core Four — Matthews, Nylander, Mitch Marner or John Tavares.

None of the four players want to leave. Matthews, Marner and Tavares will all have no-movement clauses by July 1, Nylander will have a 10-team clause and there has been no indication that any of them are willing to change their mind.

Tavares is the most logical of the four to be moved. He’s entering his age-33 season, could still extract some real value on the trade market in the form of a few younger, secondary contributors, and he’s one of the NHL’s premier faceoff men, winning at a 58.3 percent clip in all situations. Tavares is a cool and collected person by his very nature but he balked at the idea of waiving his no-movement clause earlier this month.

"I love it here. Obviously I made a commitment here for seven years to be a Leaf and I want to be here,” Tavares said. “That's how I feel. I love being captain and take that responsibility very seriously and feel really fortunate and still feel there's a tremendous opportunity for our team here in the near future and in the long run."

Tavares signed on Canada Day 2018 to great fanfare and he still has two years left on his existing contract at $11 million per season. The annual average value may be a non-starter for some teams but he’s still an attractive candidate to a contender with some cap flexibility, and still posted 36 goals and 80 points in 80 games this season. When you consider the human elements though, this becomes a lot more difficult.

In many ways, since he was a teenage prodigy, Tavares’ destiny has been to lead the Maple Leafs to their first Stanley Cup since 1967. He scored the most important goal of the past two decades, sending the Maple Leafs to the second round for the first time since 2004. His young family is settled in the tony High Park neighbourhood of Toronto’s west end. Asking him to waive his no-movement clause is akin to the sacrifice Mats Sundin was asked to make for the betterment of the Maple Leafs in 2008.

Sundin was asked by Maple Leafs management in February 2008 to waive his no-trade clause in order to facilitate a rebuild while allowing the Hall of Fame forward to join a team with genuine ambitions of winning a Stanley Cup. Toronto's star centre refused the request and his ensuing free agency took such a toll on him that he held out for part of the 2008-09 season before joining the Canucks. One of the most beloved players in franchise history, Sundin has rarely taken part in events with the Maple Leafs after retiring.

If this request fails in a similar way with Tavares, you run the risk of alienating a star player with two years remaining on his deal.

Matthews, Nylander and Marner simply can’t be moved. Matthews is too young and too good, Nylander’s contract — at least for one season — is a steal and Marner is entering his prime, he’s the team’s most valuable player, best penalty killer and defensive forward and like Tavares, grew up idolizing the Maple Leafs.

Treliving is known to take massive swings but he’s facing an uphill battle. Don’t expect a Jonathan Huberdeau-Matthew Tkachuk blockbuster trade just yet.

Explore all options to trade Matt Murray

Goaltender Matt Murray is a holdover from Dubas’s regime and the experiment didn’t work out. Murray started out the year as the nominal starter, then injuries ruined his season and by year’s end, he was the No. 3 goalie behind Ilya Samsonov and Joseph Woll, who was thrust into playoff action due to an injury suffered by Samsonov in the second round.

Murray is simply too expensive, carrying a $6.25-million cap hit and a 10-team no-trade clause. Goaltending is subject to random variation year-over-year and optimistically, you could argue that Murray was a solid starter for the Maple Leafs when he was healthy. That’s a major caveat, however, and if the Maple Leafs retain Samsonov, a restricted free agent, Murray is the odd man out.

Playing on a team with 49 percent of the salary cap tied to four players, the Maple Leafs need to sell Murray on joining a team where he would get increased playing time.

Attempt to get impending UFAs to take hometown discounts

Not all markets are created equal and the Maple Leafs can use their institutional power — or more accurately, prime location — to get players to take hometown discounts. It’s worth assessing whether Ryan O’Reilly or Michael Bunting would take below-market deals to remain as Maple Leafs.

O’Reilly was traded to the Maple Leafs at the deadline, with the Blues retaining 50 percent of his salary and the Wild incurring 25 percent so he played at a $1.875 million rate for the remainder of the season. He’s going to earn a lot more money as a free agent and Treliving will have to sell him on the idea of running it back, with an increased and further defined role in 2023-24.

Bunting is a difficult case as well. He’s due for a massive upgrade on his $950,000 salary after carving out a role as a fixture on the top line with Matthews and Marner. He led the NHL in penalties drawn at 5-on-5 and could be shifted throughout the lineup. Did he fumble his bag a bit when he earned a three-game suspension for a hit on Tampa Bay’s Erik Cernak in the first round? In all honesty, probably not.

Bunting was one of the team’s best players after returning from sanction and selling the Scarborough, Ont., native on becoming a long-term part of the Maple Leafs’ future should be one of Treliving’s top goals.