The Leafs will enter the 2024-25 with a cleaner slate than the past few years, but not everything has completely been erased. The move to Craig Berube behind the bench is a chance for a fresh start for any player in need of one and the possibility to grab a role previously unattainable under Sheldon Keefe could be there. That said, Brad Treliving is coming at the Leafs with a year’s worth of watching the team and a baseline of expectations for each player. The combination of new leadership in key hockey operations positions likely indicates several Leafs entering make-it-or-break-it seasons.

Here are five key players to watch out for:

It’s hard not to start with Liljegren. Timothy has spent his entire professional career under Sheldon Keefe and seems to have stalled at spot duty in the Top-4. Liljegren ran into injury issues in 2023-24 that stunted some of his success early in the year and by the time the season closed, it started becoming questionable whether Liljegren would play or be healthy scratched.

On paper, there is a lot to like about Liljegren as his numbers show the puck moving up the ice and chances not being as abundant with him on the ice, but there is a juxtaposition between that and eye tests which frequently accuse Liljegren of making poor coverage decisions and throwing some questionable stretch passes across the center of the ice that have come back to bite him. There is also a lot that needs to be considered when looking at Liljegren’s numbers knowing that some sheltering has occurred and when he has played up in the lineup, he had a stronger partner to support him. The numbers warrant Liljegren getting more of a look, but they are not a guarantee of future success.

At 25, Liljegren’s entering the prime of his career and he has been around the league long enough that the patience for the learning curve has likely eroded. The fact that Liljegren is a sought after right shot has likely bought him some additional leeway, but it seems that Timothy will be a player the Leafs make a decision on rather quickly into Berube’s time in Toronto.

If Liljegren looks like a fit for Berube, great. Even if in a 5D role, Liljegren is likely a better alternative than a potential post training camp replacement. If Liljegren isn’t a fit under Berube, Liljegren is a moveable asset and while creating a hole on the Leafs blueline, the potential cap savings that come with moving on from a bad fit is a reasonable consolation prize.

Liljegren also has to keep an eye on what is happening behind him on the depth chart. Philippe Myers is a sheltered bottom pairing role can do some of what the Leafs have asked of Liljegren, and if Topi Niemela has progressed since last season he too can make a case for filling a similar role at a friendly price. And of course there is also whether or not Conor Timmins’ puck movement in a bottom pairing role eliminates the need for Liljegren. Others like Cade Webber and the still possible addition of Jani Hakanpaa will also require Liljegren to have a strong training camp.

It remains to be seen whether or not Robertson will be a part of the Leafs this season. He hasn’t signed. He has requested a trade. It seems pretty clear he hasn’t had a great time in Toronto.

Craig Berube is obviously a chance at a fresh start and while Robertson’s game might not be one that screams “Craig Berube hockey,” the Leafs aren’t in a situation where they can ignore their secondary scoring options.

Assuming Robertson signs and is willing to stay in Toronto, it is clear he wants playing time and an end to the healthy scratching. That’s still an uphill battle for him. Robertson needs to find a way of adding value away from the puck. Elite shooting is a great dimension to have but he’s proving it can’t be your only thing, or at least not your only thing on the way the Leafs are constructed. He’s a great outlet for top six talent, but the Leafs can’t take the drop off in defensive play, size, and puck control that comes with having Robertson out there in key minutes. The Leafs bottom six options create question marks and perhaps Robertson’s fate as a Leaf will be dependent on him clicking with either Pontus Holmberg or Fraser Minten.

If the Leafs felt they could get a return for Robertson in trade, it seems like the team would have already moved on but reality is they need to manage Robertson as an asset. If Robertson makes it, the Leafs might ultimately decide it is in their best interest to address his trade request and recoup an asset at time when the team could use futures. The Leafs have reasonable options to replace him if that happens or if he “breaks it”. Alex Nylander, Easton Cowan, Fraser Minten, and Alex Steeves are all options after Robertson, but I’m sure the Leafs would rather sell Robertson as a potential second line winger that can put up 20 goals than his status as a player who struggled to make the lineup even now that his injury woes are behind him.

With David Kampf’s best hockey potentially in the rearview mirror and some positive reviews on Holmberg from players like Auston Matthews, it is a great time for Pontus to careve out a significant role for himself on the Leafs. He’s coming into camp with experience and a likely spot in the Leafs top 13 forwards. His versatility has shown that he can fill a bottom six centre role but also play up in the lineup if required on the wing. In the spirit of Calle Jarnkrok and Alex Kerfoot, Holmberg is the next Swiss Army knife and the Leafs have always seen value in that. At least under Sheldon Keefe.

Holmberg’s situation with Craig Berube is going to be interesting. He clearly took positive steps last season but doesn’t have the body of work or draft pedigree that it wouldn’t be possible that Holmberg could once again find himself starting back on the Marlies.

Holmberg, like Robertson, will have his role heavily defined by the status of Easton Cowan and Fraser Minten. If both rookies are ready to contribute to the Maple Leafs, Holmberg will find himself competing for depth spots on the Leafs rather than the coveted middle six roles he’ll be trying for.

Holmberg’s contract expires after this season which only adds to the make or break feel to the season for him. And while the Leafs do have other options they can move onto if Holmberg doesn’t pan out, there should be some interest in exploring his upside rather than relying on middling veteran alternatives like Kampf or Jarnkrok.

Yeah, Conor Timmins really is in make it or break it territory and with a completely buriable cap hit, there is a possibility that the Leafs might like $1.1M being sent to the Marlies more than anything Timmins can bring to the Leafs.

A complicated injury and illness history has constantly derailed what should have been a promising career for Timmins and with his contract up after 2024-25, there is an element of make it or break it for his NHL career involved here, not just looking at his time with the Leafs.

When it comes to Timmins making it, he’ll be living and dying on puck movement. He needs to show that his ability to move puck is worth keeping him in that 7D capacity if grabbing a spot in the defensive pairings isn’t possible.

Craig Berube relied heavily on puck movers like Krug, Faulk, etc and worked with their defensive inadequacies, it is entirely possible that he and Mike Van Ryn will do the same for Timmins. At the same time, Timmins’ history with Dubas and Keefe was likely a big part of giving him a chance in Toronto and despite a lot of similarities between Mike Van Ryn and Conor Timmins, it is possible that Timmins isn’t capable of fitting into the player-on-player style of defending that Van Ryn coaches.

I’m not sure how much Timmins “making it” factors into the Leafs’ plans for 2024-25, but having an additional good option on defence, especially the right side would be nice.

Penalty killing specialists are always a bit of a “buyer beware” situation and the Leafs going out and adding Dewar at the trade deadline for a fourth round pick remains a bit of a head scratcher. On the other hand, a fourth round pick isn’t an irreplaceable asset and there should still be some interest in seeing what the Leafs have in Dewar now that he’s committed to the team for one more season.

Dewar’s contract is almost entirely buriable and the $30k that would linger on the salary cap isn’t going to give Connor an edge over any alternative the Leafs might find more useable than him in their lineup, so there is a very real need for Dewar to show he’s a fit for the Leafs, which he really didn’t get a chance to do last season.

Instead, it’s a matter of looking at what the upsides are with Dewar and if he can be any of the following: a complementary option or replacement for David Kampf on the fourth line, a penalty killer that lives up to his 2022-23 successes, or a player who discovers his offensive upside from junior in the NHL. At 5’10, his size works against him, but his energy and willingness to play tough hockey fit with the culture shift the Leafs are looking for.

Dewar benefits from being a guy that Treliving specifically brought in for the Leafs to remake what was broken in their bottom six last season, that could buy him opportunities not afforded other Leafs. Connor will be one of the most interesting players to see in the initial Craig Berube line combinations.

Nick Abruzzese and Alex Steeves highlight the make it or break it options at the forward position. Steeves especially seemed on the cusp of getting NHL work last season and it slipped away from him. Abruzzese is a bit more a specialized role that is hard to cast in the NHL and it seems like the right combination of injuries need to occur before he gets recalled and gets a chance to show what he can do.

Beyond that duo, Roni Hirvonen might be the other forward to watch in regard to the Leafs making a decision on in 2024-25, as his size as well as his horrific eye injury might put the Leafs in a situation where they have to make a difficult decision at the end of the year.

Defensively, Mikko Kokkonen is very much at the point where he is what he is and that is a safe option in an organization’s defensive depth structure. His size likely earns him a look at some point but it remains to be seen if there is enough upside that the Leafs have any excitement on Kokkonen beyond the Marlies top four blueliners.

Nicolas Mattinen getting invited back into the fold for a season on the Marlies is another player who might not being making it or breaking it in regards to making the Leafs this year, but whether or not he’s part of the ongoing plans beyond this season.

And that brings us to goal and Matt Murray. Murray is absolutely in a make it or break it situation as his post hip surgery performance will quickly determine where he lands on the Leafs depth chart and if an NHL career is still viable.

The reality for this group is that some of them are going step up and others will fall flat. Between the make or break players and the prospects that could potentially come up as well, the Leafs lineup in October should be a challenge to predict. After years of looking at things through the lens of how Sheldon Keefe builds a lineup, Craig Berube opens up a lot of possibilities that will benefit some of these players and challenge some of the established parts of the core.