The Toronto Maple Leafs are looking to take another giant step forward next season. One first-round series win in almost 20 years isn’t cutting it and general manager Brad Treliving is going to do whatever he can to get his team over the hump.

At this point, there’s still many questions which need answering but of course, Rome wasn’t built in a day and it’s going to take time to piece everything together in Leafs land. Here’s three burning Maple Leaf questions heading into the 2023-24 season:

There’s a sense that Auston Matthews’ contract extension will be announced sometime in August, meanwhile the vibe isn’t the same with William Nylander. He’s already been through a tough negotiation with the organization and even though Kyle Dubas was then leading the charge, it’s likely left a bit of a sour taste in the skilled winger’s mouth.

Nylander is reportedly looking for between $9.5-10 million but it will be hard to get this type of contract the way the Leafs cap is currently structured. The NHL’s salary cap is expected to rise significantly over the next year or two so this won’t solve all the issues but it certainly helps.

With the media in Toronto and the sometimes ruthless approach, if Nylander isn’t signed before the start of the season, there’s going to be a ton of questions. If he doesn’t get off to a good start, I can already see him getting pestered by reporters after the game asking if not having a contract for next season is why he didn’t score against the Nashville Predators on a random Tuesday night in November.

I’d expect to see Treliving, Nylander or his agent come out before opening night and make a statement regarding the looming contract extension. Don’t be surprised if a deal isn’t complete, for Nylander to nip things in the butt off the jump and inform the media he won’t be fielding questions about it in season.

Matthews on the other hand, the sense is the fine details are being worked on and there is not any worries about him sticking around Toronto long term.

Besides Nylander and Matthews, don’t forget about newcomers Tyler Bertuzzi, Max Domi, and John Klingberg. They all signed one-year deals and if they get off to good starts next season, it could complicate long-term talks and make things more expensive for Treliving moving forward. What a catch-22. Don’t play too too well because we don’t want to pay you a ton of money because of our cap situation.

Add in Ilya Samsonov to this question as well, as he signed a one-year $3.55-million recently. He’s a pending unrestricted free agent and after a fine first season in Toronto, could be set up for a huge season as the team’s number one goalie in 2023-24. Needless to say, Treliving and company will be keeping a close watch on a few Leafs this season.

While personally I don’t feel there should be much concern, there’s been a lot of chatter about the long-term position of captain Tavares will the Leafs. He showed last season that he’s willing and able to do anything for the team to win as he slid over to the wing for Ryan O’Reilly at times.

This season there isn’t the same luxury as the Leafs are much thinner down the middle. Tavares will be counted on as the team’s second-line centre and this will be a developing storyline to watch heading into the early parts of next season.

While some think he’s slowing down a ton, that simply isn’t the case. Yes, his foot speed has never been his strongest attribute, but the level of concern from parts of Leafs Nation are almost laughable.

Expect to see a very motivated Tavares when the season starts as he’s healthier than ever and ready for another big year. He’ll be coming off a season where he put up a point-a-game and expect much of the same level of production and perhaps even more in 2023-24.

If things go south in a hurry next season, options include moving Nylander to down the middle or acquiring another veteran to help burden the load. The only issue is, the trade assets cupboard is very thin on inventory.

With Bertuzzi, Domi, Klingberg and Ryan Reaves joining forces with the Leafs, there’s going to be a new identity next season in Toronto. This team is going to be much tougher to play against because of the playing styles of Bertuzzi and Domi and yes, having Reavo as a security guard for the entire roster will ensure the likes of Matthew Knies won’t be getting ragged-dolled anymore.

The issue here is chemistry. Will Klingberg be able to produce again from the back end and find his ‘rover’ type game where he can jump into the rush at will and contribute? Will he mesh with Jake McCabe, as it looks like the two could be paired together next season.

As far as Bertuzzi and Domi go, they will be given every chance to succeed on the Maple Leafs. Both are expected to be in the conversation for the top two lines, with Domi a candidate to play third-line centre, depending of course how well Pontus Holmberg shows during training cap. If Holmberg is an option for the fourth line, it could move David Kampf up to the third line and allow for Domi to play the wing.

Bertuzzi is going to likely start next season with Matthews and Mitch Marner and should have himself a monster season. He will compliment those two nicely and drag them into the fight, much like Michael Bunting has done the past couple of seasons. 75 points isn’t out of the question here. Likely 40-50 for Domi and potentially another 50-points from Klingberg, should he get loads of power-play time.

Reaves won’t play much but he’ll have a huge impact with his physical presence and dressing room leadership. His contract isn’t great and he’s not the best skater, but expect a solid 10 minutes from him every game and his intimidation factor will play a role throughout the entire season and into the Stanley Cup Playoffs.

Admittedly, there are a ton of questions surrounding the Leafs so it was tough just to zone in on three. These feel like some of the burning matters to consider heading into next season. A season which the Maple Leafs are expecting to compete for a Stanley Cup.