Whether it’s the passionate fanbase, the ability to spend and buy every season, or just working in the hockey capitol, most can agree that being the Toronto Maple Leafs General Manager is a dream job.

But it also may be the most difficult heading into the 2023-24 season, as whoever earns the sought-after title may have to make their biggest decisions within their first month.

With Darren Dreger reporting that Brad Treliving is the top candidate to replace Kyle Dubas, it’s clear he is going to be tasked with figuring out what to do with Toronto’s ‘Core Four’.

Auston Matthews and Willaim Nylander are Unrestricted Free Agents (UFA) after the 2024 season, with Mitch Marner and John Tavares Mitch Marner off the books after the next two seasons.

In fact, the only players signed past 2025 is defenseman Morgan Rielly and center Calle Jarnkrok, as so much is dependent on how many of the four will stay in Toronto, and for how much.

The first hurdle for potentially extending Matthews and Nylander this year is overcoming Tavares’ contract. The Maple Leafs’ captain is owed $11 million per year over the next 2 seasons, which is still the 17th-biggest contract in NHL history.

While Tavares has accumulated 354 points in his 5 seasons since signing the deal, it’s safe to say that Toronto wishes they could have structured the deal differently, as it leaves a decision to be made with their top-tier forwards group.

The former Hart Trophy winner Matthews will certainly be asking for north of $11 million a season, and he’s not wrong in doing so, which should not be blindsiding Toronto by any means since they missed their window of extending him early.

But this could prohibit their ability to extend Marner, who led the team in points last season and is already making $10.9 million a year.

So what makes the first month so pivotal for the new GM in Toronto is the No Movement Clause attached to Matthews and Marner’s contracts, which kick into effect July 1.

While hypothetically both could be extended while staying under the cap, this postseason showed that the needs defensively and between the pipes outweighed the star power in front. And this would only be heightened if Marner and Matthews were earning more per season.

While Nylander is a hot commodity, only earning less than $7 million next year with a modified no-trade clause, the return for the 40-goal scorer last year would be fractional compared to Marner or Matthews’ potential return, which could go a long way in completing this roster.

Or Treliving could decide to go for it one final time with this core, who so far has won just one game past the second round of the postseason in their time together. Toronto still have $9 million to work with in cap space if they can make it work.

But with a restless fanbase that has seen this formula before, it may be a career-altering move to risk the future of the team one final time before losing such talent with little to show for it.