The Countdown: 4 Maple Leafs who deserve long-term contract extensions

The Toronto Maple Leafs are 16-6-6 through their first 28 games and are one of the hottest teams in the NHL. They recently blew out Kyle Dubas and the Pittsburgh Penguins and are heading into the NHL’s holiday roster freeze with firepower coming from all angles. General manager Brad Treliving has been busy since day one last summer and has completed some tidy orders of business, including re-signing Auston Matthews. Treliving still has a ton of work to be done navigating his cap space.

While Matthews re-upped for another four years, these four Maple Leafs also deserve long-term contract extensions:

After starting out as perhaps the hottest hockey player in the world this season, ‘contract year’ Nylander has slowed down a bit, but regardless, pen needs to hit paper here at some point this season. Nylander has shown off his complete game and isn’t the same player he was a couple of seasons ago when you’d get frustrated over his reluctance to go into the corners. Now, he’s going into the corners and coming out with the puck. #88 has an uncanny ability to be patient, poised and productive with the puck.

Nylander’s agent, Lewis Gross, and Treliving have spoken throughout the season and the Leafs GM made it loud and clear his priority is to get Nylander signed to a long-term deal. While Matthews only re-signed for four seasons, it could be an eight-year extension coming for #88. Both sides appear open to the option.

Through 28 games, Nylander leads the Leafs with 40 points and is doing it all over the ice and in all situations. He’s a massive part of this team, this franchise and the Swedish forward wants to leave a legacy in Toronto. It’s been a story book start to the season, including becoming the King of Stockholm for a week, and signing a contract extension early on in the new year would be the perfect start to 2024 for the Maple Leafs. Exactly what that AAV looks like? That’s a story for another day.

After Bertuzzi signed in Toronto he admitted to the media it was going to be a huge adjustment for him and he wasn’t exactly sure how things were going to play out. Well, he started quite slow on the production side of things, but of late, has managed to completely turn his game around and be a key cog for the Leafs.

One thing that keeps being said about ‘Bert’ from his new teammates in Toronto is just how crafty of a player he is, how much of an underrated passer he is and how he always seems to be around the puck. Bertuzzi isn’t the fastest skater, he doesn’t land the booming hits, he can’t clap it like Shea Weber, but he does all of the little things right and is a very good teammate. He’s always looking to make the ‘right’ play and the Sudbury, Ontario native battles each and every shift.

While his skate tongue and no-taped stick style are something that warrants a head shake, Bertuzzi sticking around Toronto should not. Certainly not an eight-year extension like Nylander may sign, but Treliving should be considering a three or four-year extension at around the same $5 million AAV he’s making this season, maybe even a little less with a longer term. Bertuzzi’s managed 5 goals and 12 points so far this season and should land somewhere around the 40-point mark after a very slow start to the year.

In one of the more underrated moves of the season, Noah Gregor has been exactly what the doctor ordered out of a bottom-six depth signing. He’s shown off his speed since day one in Toronto and head coach Sheldon Keefe loves his game, rewarding him multiple times by moving him up in the lineup, including a couple of games on the top line with Matthews and Nylander.

Gregor loves to shoot it, he loves to finish his checks and he loves flying by defencemen. Treliving should be very interested in keeping him in the fold, as the 25-year-old is quietly becoming a piece that could be very affordable and reliable among the Leafs bottom six. So far in 28 games, the Beaumont, Alberta native has sniped five goals and added two assists. He’s becoming a better penalty killer as the season goes along and is someone who remains a versatile option to move up and down the lineup should an injury occur.

Gregor appears to be enjoying his time in Toronto, so it would make sense he’s open to sticking around for the foreseeable future. With his speed and smarts, the game is there and he should be among the organization’s long-term plans, especially in a limited role among the bottom six. The fact that he’s a restricted free agent at 25 year old makes him that much more valuable, too – the Leafs will have first dibs at negotiating a new deal with him, and should take advantage of that opportunity when the summer rolls around.

Of the four players on this list, Domi’s probably the hardest to forecast. It wasn’t until recently, that he landed in a comfortable spot in the Leafs lineup, but he’s flourished as the third-line centre and continues to be a versatile option to move up, down and around the lineup.

Domi’s won 52% of his faceoffs, his offense has come on of late, and it looks like reuniting with ol’ junior buddy Mitch Marner could be something Keefe and the coaching staff explore more in 2024. While he hasn’t lit the lamp as much as he’d like, Domi has stepped up from a playmaking standpoint with 15 assists in 28 games. He’s turned many heads on the team with some of his sweet passing. Early on in the season the coaching staff was getting frustrated with his game because Domi wasn’t skating like he is now. He’s using his wheels to get into the right spots on the ice and that’s bode him well on both sides of the puck. Having a ‘Domi’ in Toronto just makes sense, and you can tell how much Max cares about creating his own legacy.

The Maple Leafs are currently projected to have over $33 million in cap space to work after this season and while Nylander is going to eat up roughly $10 million of it, the likes of Gregor, Bertuzzi and Domi should be getting some of the cake. All four players deserve to stick around and if the money is right, on a long-term basis.