The Toronto Maple Leafs aren't nearly done this offseason and there are five burning questions the team still faces heading into July.
Props to John Chayka, he's been honest with how the Maple Leafs have been recently and knew they needed change. Credit to him also for actually following through with trades that sent Joseph Woll, Simon Benoit and Brandon Carlo out of town and brought in Darren Raddysh and a lot more draft capital.
His work isn't near done though, and there's a lot of anxiety around the next few days as to what the team could end up doing, so we're here to narrow down five questions still facing Chayka and how he can answer them.
Do the Maple Leafs trade Matthew Knies or build around him?
Arguably the biggest question facing Toronto right now, especially with news that Zach Werenski is on the market - should Toronto trade Knies?
We heard there were rumblings about a potential trade to Chicago for the fourth overall pick before it was trade to Buffalo; then we heard the same thing with Buffalo heading into the draft. Nothing materialized, and it felt more like Chayka playing the field as opposed to entertaining anything serious.
But with Werenski available and the chance to make a stunning blockbuster,, there could be a chance he's on the move. There's no word on if Columbus has interest in Knies, but there has been a report that Werenski is more than happy to move to Toronto. If the Blue Jackets have interest then there's a serious opportunity to improve.
Toronto can't replace Knies but they can adapt to his absence and the additions of Werenski and Raddysh alone will add roughly 100-120 points combined with above average to elite defence. Toronto has a first line of McKenna - Matthews - Nylander, so all you're trying to do is replace Knies to go along with Easton Cowan and John Tavares.
Some targets for Toronto include Vladimir Tarasenko, Anders Lee, Mason Marchment and Michael Bunting; all of whom can add the offensive help and physicality that Knies brings.
How do they solve the goaltending after moving Woll and Ersson?
Toronto has overhauled their crease in short order as the team trade Joseph Woll for Samuel Ersson then flipped Ersson for a draft pick (which was then also traded). But they still have a little bit of a logjam with how they're approaching things.
Right now they have Anthony Stolarz penciled in as starter, and presumably Dennis Hildeby backing him up. They also have Artur Akhtyamov who impressed heavily in the postseason and looks ready to make the leap sooner than later - and there's rumours Sergei Bobrovsky is interested in coming over.
That would leave Toronto with Hildeby in the AHL yet again and as we saw earlier this year, he could be a little frustrated with a lack of playing time. If Akhtyamov pushes him out of the starter job with the Marlies, he may want out.
So if the team is expected to sign a premium free agent, they best have Hildeby on speed dial for when Stolarz inevitably goes down.
The problem isn't exactly solved until we see a future signing, but if they don't then you can expect Hildeby to get his share of starts in 2026-27.
Is Morgan Rielly actually staying or going?
Much like the song, Rielly is asking himself 'Should I stay or should I go?' He holds his own fate in his hands given he has a no-trade clause he would need to waive, but he's also given a list of teams he'd be okay leaving Toronto for.
So it seems like he's willing to leave but isn't exactly asking to be moved out of town, and he has always stated he wants to stay. This is more the Maple Leafs forcing his hand to at least open the door. But with Rielly likely in the lineup then it might not be the end of the world.
Jim Hiller is the new head coach and he has worked with Rielly before, and knows what he is capable of.
Perhaps there's going to be a new strategy that employs Rielly in a much more manageable role and it'll let him thrive. With Darren Raddysh running things now, he can take a step back and find his footing once again.
John Chayka said he was still open to offers for Rielly but had none at the current time while envisioning him as part of the lineup. It's really up in the air as to what happens with the longest tenured Maple Leaf.
Is Morgan Rielly staying or going? We have absolutely no idea.
Can they add enough to keep Auston Matthews happy and committed?
This question can't be answered in full yet, but we can absolutely say that whatever plan Chayka and company have in mind - it's working.
So far, all signs have pointed to Matthews being on board with everything the team has done so far. He wanted to see action, and has seen multiple trades, a Gavin McKenna arrival, Darren Raddysh to beef up the back end and potentially even more firepower coming in.
New reports show that Zach Werenski may only want to come to Toronto to play with Matthews and if that's the case? He has a reliable and long-time teammate who can certainly shift things in a positive way.
If Toronto can find a way to extend Werenski, then they can have two elite offensive defenders for the long-haul (something they've never had), a rookie group that consists of some incredible talent that has years to grow and get even better, and a properly built lineup that is meant to endure a long playoff push.
Nothing is guaranteed obviously, but if Chayka and Toronto keep their offseason moves as powerful and proactive as they have been, then it may be harder to convince Matthews to leave than it would be to stay.
How does Gavin McKenna fit into the win-now plan?
Finally we come to the most recent question that probably won't be answered this year which is - how will Gavin McKenna fit in? Right now, it's presumed he is the running mate alongside Auston Matthews and we'll need to see how they work together once camp opens up.
But it's a weird position to be put in. Normally, teams who get the first overall pick aren't immediately competitive and are fighting for a Stanley Cup spot so it's going to be a balancing act between featuring McKenna and also building a winning roster.
He's going to get his premium minutes, but if there are any struggles in making the leap then it may become a detriment to Toronto's playoff chances. It's hard to imagine that, but there is always the possibility.
The best chance for McKenna to fit into the win-now plans is to be an offensive factor right away and while he's capable of it, there's a chance it takes a little bit for him to get comfortable. Whether that ends up harming Toronto's playoff chances in the end is yet to be seen, but he'll certainly factor in one way or another.
What does Toronto need to focus on most this offseason?
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