Leafs offseason outlook: Biggest questions, needs, free agent targets

It was always going to be a dramatic offseason for the Toronto Maple Leafs after flaming out to the Florida Panthers in five games during their second-round playoff series. It turns out the fireworks show commenced well before Canada Day.

Maple Leafs general manager Kyle Dubas was not retained after admitting during his end-of-year press conference that the pressure of his job took a toll on him and his family. President Brendan Shanahan brought in former Calgary Flames general manager Brad Treliving to replace Dubas. Treliving hired Shane Doan as his assistant, which could prove fortuitous in upcoming negotiations as the former Arizona Coyotes forward was Auston Matthews’ favourite player as a child.

Sheldon Keefe remains as the Maple Leafs’ head coach, evidently convincing Treliving that he’s still the man for the job. Keefe may eventually return to the chopping block if the Maple Leafs stumble out of the gate, as he’ll be overseeing the most crucial season in franchise history behind the bench.

And that’s just the front office. Toronto is still positioned as a leading contender, but the roster may look dramatically different than it did at the start of the 2022-23 campaign.

Roster outlook

Notable UFAs: Ryan O’Reilly, Michael Bunting, Alexander Kerfoot, Noel Acciari, Zach Aston-Reese, Wayne Simmonds, Luke Schenn, Justin Holl, Erik Gustafsson

Notable RFAs: Ilya Samsonov, Victor Mete

Projected salary cap space: $9.134M via CapFriendly

Toronto holds relatively limited cap space entering free agency but this is a slight misnomer as the club can manipulate long-term injured reserve (LTIR) to get under the budget before the season starts. Jake Muzzin, who is owed $5.625 million for the upcoming season, will likely spend a large portion of the season on LTIR, while Nick Robertson, who will have one final chance at making a prolonged imprint on the Maple Leafs, will be freed from the reserve.

Robertson and Matthew Knies should both be part of the Maple Leafs’ regular 12-forward format next season, along with Matthews, Mitch Marner, John Tavares, William Nylander, Calle Jarnkrok and Sam Lafferty.

It will be next to impossible for Treliving and his staff to retain the majority of Toronto’s free agent class, so we’ll work with what we know. Bunting, Kerfoot and Holl are reportedly on their way out, according to a June 16 report from NHL insider Chris Johnston. Bunting significantly outperformed his two-year, $1.9-million contract and is due for a massive raise on the open market, where he’s expected to have several suitors. Kerfoot was lauded for his leadership and defensive awareness, but he’s viewed as expendable and his production never met internal expectations when paired with Tavares and Nylander.

Holl is a different case. He’s one of Keefe’s favourite players, was Toronto’s most commonly-used penalty killer and ate plenty of minutes in a coveted, right-shot position. He also was a major defensive liability and was on the ice for 18 goals during the postseason. He earned $2 million for each of the past two seasons. There will be segments of the fan base who will balk at Holl returning under any circumstances because of his fatal defensive lapses but he has some real utility at an absorbable price tag.

O’Reilly seems unlikely to return as well. St. Louis took on 50% of O’Reilly’s salary upon being traded, while Minnesota took on 25% of O’Reilly’s 2023 cap hit. Although he showed signs of slight decline, O’Reilly is still a very useful forward. He provides secondary scoring, is an elite faceoff man, can play on the wing, and is another stellar, veteran presence for a team that routinely underperforms in the playoffs. Although O’Reilly excelled in the Greater Toronto Hockey League as a teenager, a hometown discount seems unlikely.

It’s also unclear whether Scarborough-raised Simmonds would be willing to accept a diminished role for a second consecutive year. Aston-Reese made the team on a player tryout option and was particularly strong at zone exits, so if the Maple Leafs can retain him on a sub-$1M deal, it will help shape the fourth line.

Acciari was also added in the O’Reilly trade, bringing toughness and secondary scoring touch that the bottom-six sorely needed. If he can warrant a contract greater than $2-million average annual value, the 31-year-old may be gone.

Schenn was a godsend for the Maple Leafs, stabilizing the team’s top defensive pairing alongside Morgan Rielly during the playoffs. His family is settled in Toronto and Schenn spoke constantly about how much it means to him to play a major role for the Maple Leafs at this stage of his career. If Toronto can sign him to a one-year deal under $2 million, it will be a major win. Gustafsson was traded for Rasmus Sandin but his skills were largely redundant as a power-play quarterback who was a defensive liability at 5-on-5. Will the 31-year-old get rewarded for his offensive outburst during the first half of the 2022-23 campaign?

Samsonov is a top priority for the Maple Leafs. He was signed last summer to a one-year, $1.8-million contract — essentially a prove-it deal. The 26-year-old emerged as Toronto’s starter and saved 18 goals above expected per MoneyPuck, the 10th-best mark in the NHL. Although he was stellar during the regular season, Samsonov’s durability issues flared up during the playoffs and Joseph Woll started the final two games of Toronto’s postseason run. How much should a 26-year-old who was on the fringes of being considered a top-10 goalie get paid, largely based on his athleticism and a one-year sample?

Biggest needs

Third-line centre

Matthews and Tavares form one of the best centre combinations in the NHL but the Maple Leafs need to replenish their depth with O’Reilly hitting the open market, even with David Kampf re-signing on a four-year deal. Toronto could always shift Nylander to centre if need be, but the reality is it needs two permanent options with no imminent replacement coming up from the AHL’s Marlies.

We’ve factored the Maple Leafs’ delicate cap scenario into their pursuits here and aside from the unlikely option of retaining O’Reilly, J.T. Compher is the next best option. Compher is excellent defensively and can provide the secondary scoring Toronto needs, but in a relatively weak class, he may be too expensive.

Jonathan Toews isn’t the player he used to be and there are concerns about whether he’ll be healthy enough to labour through another season, but at this stage, he’s a cost-effective veteran who is still elite in the faceoff circle. He’s also won three Stanley Cups and is impervious to the stress the Maple Leafs often wilt under come playoff time. Sam Gagner could be another cost-effective fourth-line option. He produces minimal offence but doesn’t put his team in tough spots. He’s best friends with Tavares and he’s one of the most well-liked players in the NHL.

Second-pair defenceman

Toronto currently carries six defencemen under contract but Mark Giordano may retire and Holl is reportedly not coming back. This creates a void and assuming the Maple Leafs re-sign Schenn, they still need to round out the rest of their corps, as it’s unlikely that top prospect Topi Niemela will crack the opening-night roster. I love Carson Soucy as an option here. He’s a gigantic presence who can play either side of the ice. He can replace Holl on the penalty kill, he doesn’t create a ton of offence and he’s due for an expanded role.

Scott Mayfield also fits this profile and he’s an upgrade on Holl as a right-shot defenceman with less offensive ability, but he’s far more reliable defensively. Mayfield can log heavy minutes and his game took a quiet, subtle leap last season, particularly as a secondary shot creator.

Ryan Graves is also another option. He’s played in 78 games in each of the past two seasons, provides secondary offence and is a great skater who would be an ideal fit for Keefe’s system.

Free agent targets:

J.T. Compher, Jonathan Toews, Sam Gagner, Matthew Phillips, Carson Soucy, Ryan Graves, Scott Mayfield, Joonas Korpisalo

Biggest questions

Will Auston Matthews and William Nylander sign extensions?

Matthews and Nylander both have one year left on their remaining contracts and are eligible for extensions. Treliving outlined during his introductory press conference that his top priority was re-signing Matthews.

During his media availability in Nashville on Tuesday, Treliving doubled down, stating that he’s confident he can get Matthews and Nylander signed.

Matthews and Dubas built a strong professional relationship during their shared tenures and while the former Hart Trophy winner stated that his intention is to remain with the Maple Leafs, many believe he’ll sign a short-term deal rather than a seven-year pact.

Although he’s been subject to rampant trade speculation, it's hard to envision any scenario where the Maple Leafs willingly give up their cornerstone player, unless he wavers from his current stance. We'll project a three-year, $39-million deal.

Nylander wryly told reporters on May 15 that there’s still a year left on his current deal and he’s not too worried about an extension. Sportsnet’s Elliotte Friedman reported Monday that there’s still plenty of work to be done before both parties reach an extension, while Daily Faceoff’s Frank Seravalli said Treliving is accelerating his approach.

It’s been rumoured that Nylander is looking for a deal worth $9 million annually or greater. Treliving was brought in as Dubas’ replacement ostensibly because he was a deft negotiator when it came to contracts and considering that Nylander has stated on-record that he also wants to remain with the Maple Leafs, we’re projecting an eight-year extension worth $72 million.

Will Mitch Marner get traded?

Marner was the Maple Leafs’ MVP last season. He was a Selke finalist and with two years remaining on his contract, he’s an unlikely trade candidate as well. Matthews will have a full no-movement clause as of July 1, Tavares has balked at any suggestion of being traded and Nylander is working towards an extension, rendering Marner as the odd man out. Marner’s full no-move clause activates on July 1 as well, so will Treliving trade one of his superstars before free agency kicks in? It’ll be next to impossible to make a major trade otherwise.

Marner detests the idea of leaving his boyhood club and would be an unwilling trade candidate if asked to move beyond Canada Day. If Treliving wants to take a home run swing, the clock is ticking.

Can the Maple Leafs trade Matt Murray and does a buyout make sense?

Murray was projected to be the No. 1 goalie last season and by year’s end, he was No. 3 on the depth chart. Samsonov is the target here and if the Maple Leafs can sign the RFA to a new deal, Murray is once again relegated to high-paid backup status, while Woll will invariably get some more games in part due to his entry-level contract. Murray is on the books for $4,687,500 before his current deal expires.

Toronto would absorb a $687,500 hit next season and a $2 million hit in 2024-25 if it bought out Murray. Murray could also be placed on long-term injured reserve — genuinely, as he’s been prone to injury throughout his career — providing the Maple Leafs with some more cap flexibility. It’s also entirely possible Murray could be an option for teams trying to meet the salary floor (Blackhawks, Coyotes) but would the return be worth it? In any event, it looks like the Maple Leafs are trying to avoid a scenario where Murray plays a major role.