Toronto Maple Leafs: Five Burning Questions

The Toronto Maple Leafs were full of storylines this offseason. Front-office overhaul, coaching changes, the first overall pick, and a roster retool.

The list of new personnel in Toronto is long. John Chayka (GM), Mats Sundin (Senior Advisor), Judd Brackett (AGM, Player Evaluation), Freddie Hamilton (Chief of Staff), Jim Hiller (Head Coach), Daniel Alfredsson (Associate Coach), John Gruden (Assistant Coach), and Brad Werenka (Assistant Coach).

With so many changes in one offseason, there are many questions that need answers. But some questions matter more than others. Here are five burning questions to monitor throughout the season.

Toronto Maple Leafs: Five Burning Questions

Can Bobrovsky Bounce Back?

The soon-to-be 38-year-old goaltender signed with the Maple Leafs as a free agent. Toronto signed him to a three-year, $21 million deal with a $7.5 million AAV. Sergei Bobrovsky is the NHL’s oldest goaltender, but if he can provide the Maple Leafs with average goaltending and make 45 starts, Toronto could likely return to the playoffs.

Toronto hopes he is rejuvenated after a long and restful offseason. He could help the Leafs achieve even greater success if he returns to the way he played in 2024-25 (33-19-2 record with a 2.44 GAA and a .905 SV%). He will be a total bust if he plays like he did last season (career worst).

Can Often Injured Players Stay Healthy?

The health of Auston Matthews and Chris Tanev is vital to a successful Maple Leafs season. How will Matthews play after knee surgery? Have his back issues healed? Matthews returning to his dominant, goal-scoring ways would provide Toronto with a big boost.

Chris Tanev only played 11 games last season due to injuries. His defensive play (100+ blocked shots) was greatly missed last season. Having him play regularly in the Maple Leafs’ top-four on the blueline is key to their success.

How Much Impact Will Gavin McKenna Have?

The success of the first overall pick will depend on where new head coach Jim Hiller decides to play him. Gavin McKenna on the top line with Matthews seems like a no-brainer, but it’s not a sure thing. For offensive purposes, the top line is where we can see his talents shine. On the second line, Toronto can shelter him a bit by allowing him to progress without facing as much pressure.

I think he will move between the top two lines throughout the season until his perfect fit is found. McKenna has all the tools to register 60 points in his rookie season.

Is Darren Raddysh Worth It?

The sign-and-trade for Darren Raddysh before the defenseman hit the free-agent market was one of John Chayka’s biggest moves this offseason. Toronto signed the hard-shooting defenseman to an 8-year deal worth $68 million ($8.5 million AAV).

He registered 22 goals and 48 assists for 70 points in 73 games last season. Before that, the 30-year-old never reached 40 points. However, last season he was given a bigger role, and he made the most of it. Toronto is hoping last season wasn’t a fluke.

The Number One Burning Question Is…

How Will New Head Coach Jim Hiller Perform?

The former Leafs’ assistant coach (under Mike Babcock) and Los Angeles Kings head coach has a big job in front of him. He will be counted on to reignite the Toronto power play, improve how the Maple Leafs play defense, and manage the many personalities throughout his lineup.

How he uses players like Matthews, McKenna, Raddysh, Matthew Knies, Easton Cowan, Bobrovsky, and others will be under the microscope. This is his second chance at being an NHL head coach. He needs to make the most of it and rely on those around him for help.