5 burning questions for Maple Leafs’ management during offseason

The work is just beginning for Toronto Maple Leafs’ management as the season has come to an end.

Maple Leafs president Brendan Shanahan and general manager Brad Treliving have preached major changes this offseason and some heavy lifting is on the way. There’s a number of changes coming, which are inevitable in a salary cap world. Shanahan and Treliving will need to hire a new head coach in the coming weeks but it’s going to be about much more than just a new voice behind the bench.

Here’s five burning questions for Shanahan and Treliving as the ‘summer of change’ begins:

Who Becomes Toronto’s New Bench Boss?

Sheldon Keefe did a fine job as the Maple Leafs head coach for five seasons. Taking one of the more polarizing jobs in sports with no NHL experience should be applauded and Keefe’s regular season success was quite impressive. Yes, the results didn’t translate to much playoff success but Keefe wasn’t necessarily the ‘problem’ — it was just determined that new direction and outlook was needed.

Keefe’s going to land on his feet in the very near future and has already been linked to jobs in New Jersey and Winnipeg. A former junior hockey superstar, Keefe changed the narrative around him and left the organization on a classy note.

When it comes to the next coach, Craig Berube and Todd McLellan appear to be the frontrunners so far, according to TSN’s Darren Dreger.

Maple Leafs management reportedly wants to get someone in as soon as possible, and there is a real sense of urgency but they’re not going to hire someone just for the sake of it. They must get this right.

Berube and McLellan should be considered the favourites, while Gerard Gallant, Bruce Boudreau, Joel Quenneville and a few other veteran coaches are likely to remain in the mix.  Treliving and Shanahan surely aren’t going to bring in a rookie NHL coach, like Kyle Dubas did with Keefe five years ago.

It’s also worth noting the associate coaches are likely to change and rightfully so. Guy Boucher, come on down. Boucher ran the power play, even though he hadn’t necessarily had this responsibility in his past, and he wasn’t able to get the Leafs’ PP units on track. Eventually it caught up to them in the worst way possible. It’s borderline shocking he still has a job but that could very well be changing once the new head coach is named.

Who Becomes Joseph Woll’s New Partner?

Treliving praised Woll throughout the end-of-year press conference and mentioned numerous times he believes in the 25-year-old goaltender. There’s an emphasis on ensuring Woll stays healthy by potentially altering his training program. Ilya Samsonov did not receive the same type of love from Treliving, with one passing mention about his contract.

The writing is on the wall for Samsonov as he’s going to hit free agency and will land on his feet. Treliving will likely need to hit the trade market to find Woll a new counterpart. It needs to be a veteran with playoff experience, under contract at a reasonable cap hit and can help move the needle for the Maple Leafs. Should be easy to find, no! This can’t be a patchwork type of move to give Dennis Hildeby another year or two in the minors. Treliving needs to make sure he hits a home run and doesn’t even consider dropping down a bunt single.

There’s already been some names floating around including Jacob Markstrom, Ilya Sorokin, Adin Hill, Filip Gustavsson and Tristan Jarry. It’s all going to come down to how much Treliving is willing to part with to make it happen.

‘We Will Look at Everything’…Who Does That Include?

Shanahan mentioned ‘we will look at everything’ this summer, which may have been the pull quote from Friday’s presser. This is a new message from Toronto’s long-tenured president. Year after year, Shanahan and company went to bat for the core of this team and felt the success was coming, it was just a matter of time. Time’s up, folks.

Who will management be willing to part with? Mitch Marner and John Tavares certainly hover around the top of the list based on their contract situations and fit the ‘major changes’ narrative; as we all know, both have no-movement clauses and any trade involving either will be very complex.

Auston Matthews appears destined to be the next captain of the Maple Leafs, but he’s likely going to have to wait another season until Tavares plays out the final season on his contract. Even if Tavares is re-signed at a hometown discount, the formal leadership change in Toronto’s dressing room is likely not too far off.

As for possible trade candidates, what are Treliving’s thoughts on Nick Robertson or Timothy Liljegren? Both players had very inconsistent seasons and went in and out of Keefe’s dog house throughout this past season. Both players also happen to be restricted free agents heading into the summer and it won’t be long before Treliving plays his cards on their future with either a contract extension or potentially including them in a trade package, perhaps for a goaltender.

It’s worth noting Treliving has pulled off some bold trades in his past and he’ll have a solid grasp on what each of his core players could fetch in a potential trade. He loves to be active in conversations on how to improve his hockey club. Talk is cheap though, it’s time for some action.

Will Tyler Bertuzzi and Max Domi Be Re-Signed?

Max Domi and Tyler Bertuzzi made it very clear after the first-round exit that they want to return to Toronto. After slow starts for both forwards, they were able to turn things around and ended up finishing their first season as Leafs in the good books with the coaching staff and importantly, with the fan base.

Treliving has $18.5 million in projected cap space to work with and potentially even more if some trades happen at the NHL Draft, so there’s certainly room for both Domi and Bertuzzi to return. The players will push for long-term stability. Adding some term to both contracts could allow for Treliving to keep the annual cap hits at an affordable figure and maintain a bit of flexibility this offseason.

These two extensions are likely among the top of Treliving’s to-do list and he’ll want to get them out of the way long before free agency opens on July 1.

Who Will the Leafs Target in Free Agency?

Treliving added the ‘snot’ and ‘pi-- and vinegar’ in his first offseason, so what will be the theme this summer? Assuming Domi and Bertuzzi re-sign and Treliving cleans up his restricted free agents including Robertson, Liljegren, Noah Gregor and Connor Dewar, the $18.5 million in cap space will evaporate quickly.

Any trade involving Marner or bringing in a goalie is going to sway the finances one way or another, so it’s going to be interesting to see how much flexibility Treliving has to be aggressive come July 1. The defense core needs serious attention this summer and it’s time to get Morgan Rielly some legitimate top-four help.

Brett Pesce, Brady Skjei and Brandon Montour are among some of the notable free agents, but at this point certainly feel like pipe dreams. The next tier includes Matt Dumba, who Treliving tried to sign last summer and Matt Roy, Sean Walker, Dylan DeMelo, Nikita Zadorov, Alexandre Carrier, Chris Tanev, and Alec Martinez.

There’s also pending unrestricted free agents Joel Edmundson and Ilya Lyubushkin to consider bringing back. Lyubushkin shouldn’t be getting first-pair minutes next season and needs to be pushed down the depth chart to maximize his efficiency. Edmundson proved his worth in the playoffs and if the money is right, both could and should be back.

The goaltending free-agent market is paper thin. Cam Talbot and Alex Nedeljkovic aren’t going to cut it for this Leafs team who continue to get ‘goalied’ in every playoff series. Treliving’s noticed and fully expect to see him look for a 1-A type of starter via trade.

There is a potentially bold move: an attempt to sign Steven Stamkos. Again, this one feels like a pipe dream at this point and a return to Tampa Bay remains extremely likely for Stamkos. It’s no secret Montreal, Detroit and Nashville are ready to pounce. Toronto swung-and-missed many moons ago on signing Stamkos and time will tell if they even consider it given its financial structure. It’s much more likely they get away from having almost have of the team’s cap space tied up into four forwards. As we all know, this is not a recipe for playoff success.

Some free-agent forwards to keep an eye on include Sean Monahan, Chandler Stephenson, Elias Lindholm, Viktor Arvidsson, Sam Lafferty and Sam Carrick. The aggressiveness will come down to ability to spend, so unless Treliving finds some trade partners around at the NHL Draft, it’s much more likely to see Leafs management make their major changes via trade.

Five burning questions are hovering over the Leafs brass, meanwhile the perfect answers are nowhere to be found. It does appear management is finally committed to making a slew of bold moves, which could include blowing up the core of the team. Time will tell if they can execute their vision.