Toronto is not only fighting against the clock when it comes to Auston Matthews, but also against Gavin McKenna's path to being a franchise cornerstone.
Time is not on the side of John Chayka right now, considering that he only has a short period to not only field a competitive team built for the playoffs before Auston Matthews' deal is up, but he also needs to make sure he prepares properly for Gavin McKenna's future.
All the moves Chayka made this offseason have been with the intention of winning now, and the fact that he traded away nearly his entire goaltending group while revamping the bottom-six, the future isn't on his mind - only the next two years.
Clock one runs out when Matthews' deal expires
Toronto added Nick Paul, Colton Sissons, Teddy Blueger, Brandon Duhaime, and Jack Roslovic to the mix, which is a complete overhaul from the bottom-six we've seen the past two seasons.
They're more defensively sound, tougher, feistier, and are meant to be players who not only get the Maple Leafs back into the playoffs, but keep them there longer than the second round.
If the team doesn't become competitive this season, that's only going to accelerate the timeline with the only hope being a year together is enough time for the new players to gel and find chemistry then build on it even further in order to guarantee a playoff spot in 2027-28.
Matthews' patience has been outstanding considering the fact he's never come close to winning in Toronto. But loyalty has a timeframe in some cases, and the longer he sticks around without a Cup, the more he may regret his decision later on.
Toronto's spending $16.5-million in salary (annually) on just the bottom-six, and when you add in Sergei Bobrovsky's $7-million AAV, it becomes clearer that Chayka's desire isn't to build the Maple Leafs of the future just yet - he wants to get them a Cup first.
Though that's certainly not guaranteed, and if the next two seasons don't play out how his plan envisioned, then he'll need to pivot because not only will he be asking what happened, but he'll be without Auston Matthews going forward.
Clock two doesn't start until McKenna is ready
If that's the case, then it's going to be Gavin McKenna's team. But the question then becomes - is he going to be ready?
He's only 18 years old, and is going to be 20 when Matthews' contract is up.
McKenna had 15 goals and 51 points in 35 games at Penn State, was Big Ten scoring champion, Big Ten Freshman of the Year, set freshman program records in assists and points - certainly a generational talent.
McKenna's still going to be a couple years away from truly coming into his own but he's likely going to get expensive quick and that's before he hits his prime years.
Right now he's on an ELC for three years and it's very likely he's going to burn through that first year immediately. (If a rookie plays 10 games or more, they don't get the contract slide). Though playoff games count in that slide, it's likely he plays more than 9 games total for Toronto.
Basically, if Toronto only played McKenna for 9 games then he would have an extra year of control. That's unlikely to happen, and his contract expires in 2029.
That deal comes at a cost of $1.075-million cap hit on his salary and he can earn up to $4.575-million with performance bonuses though the cap hit stays at that $1.075-million figure.
If they can't afford McKenna's bonuses this season, that gets pushed onto next year's cap though they'd still need to navigate their finances if they're still over, and makes things tougher for John Chayka fighting against time.
While his next deal depends on his results, odds are he's going to become a star and demand a heavy pay increase. Toronto can't lock him down to an eight-year deal anymore thanks to the new CBA, but they can give him seven.
That might come at a heavy cost as we saw with Connor Bedard and Ivan Demidov's extensions, leaving little room for other moves.
Bedard signed for $15-million AAV, meanwhile Carlsson is the highest-paid player at $18-million AAV, and both men signed shorter deals allowing them to make even more money just as they hit their prime and McKenna could follow suit.
That also is a heavy commitment when you need to decide if you're keeping Auston Matthews as well, because with only a projected cap of $123-million in 2028-29 (per Puckpedia), you could see at least $15-million of that total cap go towards McKenna, with another large portion reserved for Matthews (with over 10 players needing new deals).
Toronto has to make sure that Jim Hiller, the rest of the coaches, trainers, and everyone involved are preparing McKenna for the road ahead. Hiller's role right now is two-fold - he needs to strategize a lineup in order to compete, but also give McKenna enough room to grow (which also includes failing).
It'll take time for the Maple Leafs to know exactly where McKenna is going to stand in a few years, and they need to do everything in their power to help him grow considering it's likely he's here longer than Matthews.
Which means that first clock is ticking, and it might be too late for John Chayka to buy more time. Especially considering that just when he had a chance to reset, he has to pay Gavin McKenna.
What is more important to the Maple Leafs right now?
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