6 burning questions for the Maple Leafs entering the offseason

Where do we go from here?

If you’re a fan of the Toronto Maple Leafs or a journalist covering the team, this simple question may be ringing at high-volume on an otherwise pleasant Saturday afternoon. Toronto was eliminated in five games by the Florida Panthers and now the post-mortem begins.

We’re not going to waste your time with the preamble, so here are six burning questions the Maple Leafs need to answer this offseason.

Should the Maple Leafs fire Sheldon Keefe and/or Kyle Dubas?

In my season preview, I wrote that the 2022-23 Maple Leafs were created entirely in Dubas’ visage and that he couldn’t blame the failures of this group on previous regimes. Dubas aggressively improved the roster at the deadline, adding Ryan O’Reilly, Noel Acciari, Sam Lafferty, Luke Schenn, Jake McCabe and Erik Gustafsson, sending a message to his team’s best players that no avenue would be too ambitious in pursuit of a Stanley Cup.

From the press box, Dubas was often heard screaming about missed calls or demanding more from his best players, and this is a good quality to have, you want your general manager to be passionate. My opinion wavered over the course of the season — particularly after the deadline — believing that Dubas should be retained for his aggressive approach to improving the roster. His five-year contract has now expired and whether he remains with the Maple Leafs is a decision that will reverberate around the franchise for years to come.

Dubas is considered to be an attractive target for other teams — it feels like he could be swayed to elevate to a president of hockey operations role with the Flames or Penguins, if he receives an offer. It’s resoundingly clear that the 37-year-old wants to win with the Maple Leafs. You don’t need press access to see how badly he wants the team he built, for the club he grew up idolizing, to get a chance to party like it’s 1967. Unfortunately, there’s a built-in paradox as Dubas has built one of the NHL’s most talented rosters that constantly performs below expectations in the playoffs.

As for Keefe, he may be gone. Keefe is a players’ coach through and through; he defends his players from the criticism allayed from media and fans alike, and he’s acutely aware of the unique pressures of performing in a hockey-mad market. Keefe has a .678 winning percentage during his 267 regular season games with the Maple Leafs and a .433 winning percentage in his 30 postseason games. He has a tendency to overthink lineup combinations and then get upset with the media for showing curiosity with his experiments or anything that goes beyond the standard "pucks in deep" fare. Jon Cooper and Paul Maurice both said Keefe is an excellent coach following their series victories, but they also bested him quite comprehensively in consecutive series where the Maple Leafs had home-ice advantage.

If Keefe gets fired, I’m sure he’ll be picked up elsewhere in no time. He was the right man to take over for Mike Babcock, whose cruelty to his own players is well-documented. Toronto needs to find an aggressive tactician who won’t coddle the players, but will approach the playoffs with a less reactive, more proactive approach. And now we wait to see if the Maple Leafs run it back with their high-profile executive duo.

Will any of the Core Four get traded?

Mitch Marner, Auston Matthews, William Nylander and John Tavares are objectively as good as any quartet in the league, but they also account for 49% of the team’s salary cap and if you follow the Maple Leafs, you know what the definition of insanity is.

Marner balked at the idea that this would be the final year for the Core Four, plus longtime mainstay Morgan Rielly, who just completed the first year of an eight-year extension.

"We all have years on our contracts," Marner said following the Game 5 loss to the Panthers. "It's not up to us but we've got a lot of belief in this group and a lot of belief in that core. But, yeah it sucks right now, but we've got belief."

Marner is right. It does suck right now, but the Core Four are indeed under contract for one more year — Matthews and Nylander are free agents at the end of the 2023-24 season. It won’t appease the hurt of Maple Leafs fans, but next year is the Last Dance, not this year.

Without seeming like an apologist, it feels unlikely that the Maple Leafs would get anything close to fair return on value if they traded one of their top four. Matthews and Marner are firmly among the league’s best 15 players and we don’t anticipate a Matthew Tkachuk-type of blockbuster trade. Nylander’s contract, a shade under $7 million, is one of the best values in the league.

Tavares and his family are from the Greater Toronto Area and entering his age-33 season, it’s unlikely he would get traded for a player of equal value that fits the Maple Leafs’ win-now-or-else timeline. However, Tavares has a no-movement clause and it’ll be next to impossible to trade him without a long consultation. And though he’s envisioned lifting the cup with the Maple Leafs for the entirety of his hockey career, which has played out in public for two decades, he’s the odd man out if Toronto can find a top-line center who is younger and can approximate similar value.

Matthews and Nylander are eligible for extensions on July 1. Matthews didn’t record a goal during the five-game loss to the Panthers, and there’s reason to be frustrated that his superior underlying numbers didn’t translate into actual goals when the Maple Leafs needed him most, but it would be malpractice if the team decided to let their homegrown stars leave without a prolonged fight. One more year and then you can burn the building to the ground if you please.

Has Joseph Woll earned a permanent spot with the Maple Leafs?

Woll was never supposed to be the starting goaltender for the Maple Leafs during their final game of the year, but Ilya Samsonov and Matt Murray both picked up injuries and the 24-year-old performed admirably. He spent the majority of the season as one of the AHL’s best goaltenders and in a small sample, excelled for the Maple Leafs. It’s fair to say that he’s earned a promotion, while playing on a team-friendly $766,667 salary for the next two seasons.

The difference between an AHL and NHL goalie is often figuring out the mental side of the game, Woll is beloved by his Maple Leafs teammates, earning their respect for keeping them in the fight while thrust into emergency duty. He’s already a better option than Matt Murray and should be one of the two roster goalies next year.

Who will be the starting goaltender next season?

What a difference a year makes. Murray was supposed to be the nominal starter with Dubas betting on his playoff pedigree, while Ilya Samsonov joined the team on a show-me deal, failing to secure the starting job for the Capitals. Goaltending is the hardest element to predict year-over-year and the experiment largely worked, albeit in unforeseen ways.

Samsonov emerged as the starting goaltender and saved 18 goals above expected via MoneyPuck, the 10th-best mark in the league. He kept the Maple Leafs in games but he was also prone to allowing untimely, bad goals, a lesser-profile Frederik Andersen-type if you will. Murray started the year strong but injuries doomed his season and his form dipped completely after November ended.

Murray is owed $4.69 million for the upcoming season, while Samsonov is a restricted free agent. Although starting goaltenders are difficult to come by, it’s probably for the best if the Maple Leafs trade Murray to a team looking to meet the salary floor — Coyotes, Blue Jackets and Blackhawks, pick up the phone — while making room for Woll’s ascension and a small raise for Samsonov.

How many of the Maple Leafs’ unrestricted free agents will be retained?

Toronto’s all-in approach at the deadline resulted in a second-round exit, which can be attributed to but not excused by some poor shooting luck and sub-optimal coaching. So if the process resulted in a disappointing ending, should the Maple Leafs run it back?

Matthews, Marner, Nylander, Tavares, Rielly, Murray, Matthew Knies, Calle Jarnkrok, TJ Brodie, Mark Giordano, Timothy Liljegren, Nick Robertson and Conor Timmins are all under contract for next season. Deadline acquisitions Jake McCabe and Sam Lafferty are also signed through 2024, while Jake Muzzin’s contract could be placed on long-term injured reserve again, if he’s unfit to start the year with a cervical spine injury — he’s actively been around the team and despite the severity of the injury, hasn’t indicated that he’s going to retire soon.

CapFriendly listed the Maple Leafs’ free agents as the team has $8.3 million in cap space for the 2023-24 season with 17 players under contract. The first priority should be to sign Ryan O’Reilly to a short-term deal — with the allure of playing his hometown Maple Leafs as a factor — on a contract under $3 million per season. This may be wishful thinking of course, and if O’Reilly leaves, Michael Bunting should be the next priority. Bunting will need a large raise from his $950,000 salary, but he may be more valuable on the open market. Another team will certainly be able to offer him a longer-term contract than the Maple Leafs can.

Luke Schenn was outstanding during the playoffs and it’s rumoured that he will return to the Maple Leafs on a team-friendly deal, but it also may be the last time he’s up for a new contract during his lengthy career. Schenn should be back with the team. Noel Acciari should be a priority as well, as he stabilized the bottom-six upon joining the team.

Alexander Kerfoot is likely gone because he’ll be too expensive.

My guess is that the Maple Leafs retain O’Reilly, Acciari, Bunting, Schenn, Wayne Simmonds and Zach Aston-Reese, while Kerfoot, David Kampf, Justin Holl, Erik Gustafsson, Victor Mete and Pontus Holmberg are on their way out. This may read as too ambitious, but the Maple Leafs know how to use the LTIR to do some cap gymnastics.

Where does Matthew Knies slot in?

Knies was a revelation for the Maple Leafs during the playoffs and now he’s likely a fixture in the team’s top-six. This will allow Kerfoot to walk in the offseason, as Knies offers a high-end skill set with excellent puck support and physicality to excel in the NHL immediately. I’d imagine he starts the year with Tavares and Nylander as his most common linemates.