6 big questions for the Toronto Maple Leafs’ off-season

Brendan Shanahan explains to the media why he believes the Toronto Maple Leafs can win a Stanley Cup with the current core players on their roster.

TORONTO – Even though Kyle Dubas has already been one of the busiest general managers in this young off-season, he won’t be able to let his foot of the gas for the rest of the month.

New cap-friendly deals for pending UFAs and dressing-room-culture icons Wayne Simmonds and Jason Spezza have brought some clarity to the 2021-22 Toronto Maple Leafs’ fourth line. An agreement with pending RFA Travis Dermott gave the promising defenceman some financial security — if not geographical security. And the Leafs waved goodbye to the first coach of the Seattle Kraken, replacing him with Dean Chynoweth Monday.

These moves are nothing more than an amuse-bouche for the main course to come.

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Trade rumours are buzzing, and Toronto still has final decisions to make on a pair of long-term players.

Let’s look at the six biggest questions facing the club before the NHL’s shortest off-season goes full frenzy.

Who will the Leafs lose in the expansion draft?

We predict great fervor Saturday when 30 teams release their protection lists for the Seattle expansion draft, but we suspect Toronto already has a good idea which player will get swallowed by the Kraken.

Our prediction: Dubas protects his core four forwards, top four defencemen and Jack Campbell.

This would leave forward Alexander Kerfoot, Demott and forward Pierre Engvall as the top three candidates to get plucked.

When Dubas re-signed Dermott to a two-year extension Thursday, he made the player no promises, but gave him a raise and some security no matter what happens.

Yes, Toronto will lose a much more valuable asset this time around (it lost Brendan Leipsic to the Vegas Golden Knights in 2017), but several teams are in a much tighter bind.

And if Kraken GM Ron Francis does scoop Kerfoot, that’ll free up cap space to sign a player of similar pedigree.

Who will be Campbell’s partner?

The bad news: Right now, the Maple Leafs are staring at an 82-game schedule with only one NHL-level starting goaltender in the fold — and he’s never played more than 31 games in a single season.

The good news: Frederik Andersen’s $5 million is coming off the books, and management can use a portion of that to go shopping in a buyers’ market.

Watching the Tampa Bay Lightning and Montreal Canadiens reach the fourth round on the strength of their netminders is a reminder of the importance of the position.

So. Who will Jack Campbell’s tandem partner be?

Once Seattle makes its selections — and an acquired goalie needn’t be protected — the carousel should kick into high gear.

The options here are manifold. Choose your own adventure.

Dubas could simply try to bring back Auston Matthews’ bestie, the overworked Andersen, at a reduced rate and term and hope that he can regain form.

He could explore a trade for a proven talent on a rebuilding team: Elvis Merzlikins or Joonas Korpisalo with the Columbus Blue Jackets; John Gibson with the Anaheim Ducks; or Darcy Kuemper with the Arizona Coyotes.

He could swing bigger and help solve Vegas’s crowded crease (Marc-Andre Fleury or Robin Lehner) or poach emerging star Alex Nedeljkovic from the Carolina Hurricanes. (Opinion: The Hurricanes should not let go of Ned.)

Or he could save a few bucks and snatch up a second-tier UFA — Chris Driedger, Jaroslav Halak, Linus Ullmark, Petr Mrazek, Antti Raanta — and bank on Campbell’s breakout 2021 rolling full steam into 2022.

What happens with Hyman and a left wing that needs a lock?

Tyler Bertuzzi (RFA) is the latest name linked to the Leafs, as Toronto must either re-sign Zach Hyman (UFA) or get creative in filling his hardworking boots with a more affordable option.

The Bertuzzi pursuit is a compelling one, and he likely could be signed for a shorter term than coveted UFA options Taylor Hall, Gabriel Landeskog and Jaden Schwartz.

We wouldn’t slam the door on Hyman just yet, as the Ryan Nugent-Hopkins extension with the Edmonton Oilers laid out an example of giving up maximum term to minimize cap hit.

But even if prospect Nick Robertson lives up to his offensive potential, Toronto still needs a second left winger to excel in its top six.

Jeff Marek and Elliotte Friedman talk to a lot of people around the hockey world, and then they tell listeners all about what they’ve heard and what they think about it.

Will the third line develop an identity?

Paying four forwards more than $40 million has made it nearly impossible for Toronto to roll four lines and dress the type of dependable checking unit that Tampa rode to glory.

Alexander Kerfoot and Ilya Mikheyev are great skaters and responsible defenders, but there has long been a missing ingredient in the middle of the forward group.

Internally, the goal is to win a Stanley Cup. We don’t see a way Toronto can afford a third unit anywhere near the calibre of Barclay Goodrow–Yanni Gourde–Blake Coleman. (Frankly, Tampa can’t afford that group anymore, either.)

Through trade and/or bargain hunting and/or graduating Marlies (Joey Anderson? Adam Brooks?) the organization must do its best to cobble a third line that coach Sheldon Keefe trusts.

They’ll get clarity on Rielly’s future, right?!

A pattern has emerged, and it’s based on ambition.

Forever wishing to reward the group midseason and always in go-for-it mode, the Maple Leafs have held on to their pending UFAs as “own rentals,” even when they knew those useful players were going to walk out the door.

First it was Tyler Bozak and James van Riemsdyk. Then Tyson Barrie. And now, it appears, Hyman and Andersen.

Morgan Rielly is too valuable an asset to play this wait-and-see game.

Dubas should have a firm handle on Rielly’s price as an unrestricted free agent next summer (2022) and make a call.

Either decide that his busiest defenceman is worth a raise and commit — or decide that Rielly’s price is too high and trade him for a haul this summer while the GM still has some leverage.

This situation is as complicated as it is important. Rielly bleeds blue and white. He’s a leader coming off a fine post-season. But he is not an elite penalty-killer, and his status as Toronto’s top power-play quarterback is now in jeopardy thanks to the younger, cheaper Rasmus Sandin.

Gather draft picks or nah?

Due to their aggressive renting at the deadline, the Maple Leafs will have just one pick (a second-rounder) through the first four rounds of July’s draft. They’ve already spent eight of their 14 picks in the next two drafts.

Dubas did well by his scouts in the 2020 off-season, recouping a first-rounder from the Pittsburgh Penguins for Kasperi Kapanen. Is there a creative way to free cap space and gain some draft capital on the floor this summer?

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