Maple Leafs offseason: What should Toronto do with Kyle Dubas, Auston Matthews, free agency, trades

May 28, 2023

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Toronto was ousted early from the playoffs despite lofty expectations. We go over what the franchise should do moving forward.

The Toronto Maple Leafs have entered most seasons in recent memory with lofty expectations of reaching the Stanley Cup and winning a championship for the first time since 1967. In 2023, the biggest hurdle was making it past the first round. Toronto did so by eliminating the defending Eastern Conference champion Tampa Bay Lightning in six games. But just when you thought the team had turned a corner, the Leafs run into the Florida Panthers as the second Wild Card and fall flat. Toronto is bounced from the postseason in five games in a playoff the team could have easily won.

So where do the Maple Leafs go from here?

It's a pivotal offseason for the franchise. Up top, it's unclear if general manager Kyle Dubas will be back. He's said it will be more of a family discussion, but you’d have to think Maple Leafs president Brendan Shanahan would have the final say. It feels like Shanahan will (and should) get rid of Dubas and go in another direction. At this point, we’re waiting to see what happens with Dubas. From there, we’d move down and look at what the Leafs should do with the roster.

The biggest concern is Auston Matthews and his next contract. Matthews, 25, will enter the final year of his current deal worth an average annual salary of $11.6 million in 2023-24. After that, Matthews can test free agency. The All-Star center has already mentioned his intention to stay in Toronto. The Maple Leafs will almost certainly look to bring back Matthews on a massive deal that could set the record for salary in the NHL. But is that the right decision? As crazy as that sounds, it's worth discussing.

Matthews was drafted in 2016 and Toronto has been to the playoffs in every season since then. It's resulted in a handful of first-round exits and this season, winning one series. Matthews is still only 25 years old and is probably just entering his prime. While Toronto hasn't been able to win with Matthews yet, the odds the team can win without him would almost certainly go down.

The issue could be cap flexibility. John Tavares and Mitch Marner are signed through one additional season beyond Matthews. There will be one overlap year where, if Matthews is making between $12-14 million, the cap dance could get tricky. Chances are the Leafs don't bring back Tavares on a new deal, but that wouldn't be until after or during the 2024-25 season.

The Leafs also need to re-sign William Nylander the same time as Matthews. Nylander could command around $8-9 million per season coming off a contract worth close to $7M. That could be north of $20 million in cap going to Matthews and Nylander, plus the near $22M in money going to Marner and Tavares. So you have over $40M in cap tied to four players who haven't been able to win together.

The Maple Leafs also have a bunch of pending unrestricted free agents, including Ryan O’Reilly, Alexander Kerfoot, Noel Acciari, Michael Bunting and David Kampf. ROR figures to find a decent last contract in free agency as a veteran looking to win a Cup. He also is from Ontario and may want to stay in Toronto on a discount. Outside of O’Reilly, none of the other UFA players did much in the postseason. But if the Leafs let most of them walk, how do you fill out the roster knowing you’re committing a ton of salary up top? You may need to make a tough call.

That could be moving Nylander for assets, particularly a potential top-pairing defenseman. Defense has always been a weak point for the Maple Leafs, the team using veterans and trade-deadline acquisitions to patch things up. It hasn't worked out well the past few seasons. Morgan Rielly is a fine mid-pairing, power-play specialist. TJ Brodie and Mark Giordano are past their primes yet still on the team for another season. Jake McCabe and Timothy Liljegren have potential on cheap deals but neither projects as a top guy. There's also no one coming through the pipeline anytime soon.

So Nylander may be the player the Leafs opt to move for salary relief/to recoup assets. The ideal time would be before the 2023 NHL Draft, where you could grab a first-round pick in a deep class, plus add a young defenseman who can grow into a top-pairing puck-mover. There is the crazy alternative: Trade Matthews.

Now, this is a difficult trade to navigate and the other team would need to know he's committed. There's also the fact leverage falls apart if other teams know Matthews wants out or the Leafs want to trade him since he's going to hit the open market soon anyway. There are a few teams that could swing a deal for Matthews and the two that stand out are the Los Angeles Kings and Detroit Red Wings.

The Kings are going to have to deal players anyway. Kevin Fiala, Adrian Kempe, Phillip Danault, Trevor Moore and Alex Iaffalo are all signed long term. Anze Kopitar and Viktor Arvidsson will need new deals soon. After them, Quinton Byfield, Blake Lizzotte, Gabe Vilardi and Arthur Kaliyev are restricted free agents and will need new contracts. Matt Roy, Sean Durzi, Sean Walker and Vladislav Gavrikov will also need contracts. So the Kings have a lot of decisions to make.

Shipping out a top prospect like Byfield or Brandt Clarke, plus picks and a few NHL players and you could get to a place where Toronto would entertain giving up Matthews. The Leafs can keep Nylander at a smaller price tag and re-sign Marner. Toronto stays competitive and can add in some youth and depth. The Kings become more of a contender in the West and can re-sign Matthews if Kopitar exits.

It's hard to imagine the Leafs trading Matthews to a team like the Red Wings, a rival and division opponent. But Detroit has the prospects and picks to pull off a deal like this. Dangling Lucas Raymond, while not appealing to fans, would be fine. Raymond and/or another top prospect like Simon Edvinsson, Marco Kasper or Jonatan Berggren, plus picks could get it done. The Red Wings have five picks in the first two rounds in 2023.

But if you’re the Maple Leafs, it will never make sense to trade the franchise center over the wing. So moving Nylander makes the most sense. It's just going to be very difficult for Dubas (or any other GM) to navigate the cap and put together a championship team with Matthews, Marner, Tavares and Nylander taking up half your cap space. And that's without addressing concerns on the blue line and at goaltender.

It isn't that Matthews’ next contract is a problem. It's really only going to be a $2-3M raise, so that isn't bad on the cap. It's paying Marner and Nylander. Marner you have to bring back. If Nylander wants $8-9M, that's a lot of money you can allocate to add depth in the bottom six forward group and on the blue line. You could also look to add some cheap goaltending. That seems to be the way to go now when looking at some top teams like New Jersey, Boston, Minnesota and Colorado.

So the best course of action for Toronto feels like this. Get rid of Dubas and bring in a veteran GM or someone with a bit more experience who has operated under a successful GM. Think someone working with Jim Nill in Dallas, someone from Boston or Tampa Bay's front offices. Do this sooner rather than later so you can prepare for the draft and free agency.

Next, ship out Nylander as much as it might sting. Really unless you can move Tavares’ $10M over the next two seasons, Nylander is your best bet to get some cap relief and bring back quality assets. You have Matthew Knies as a potential cheap top-6 forward who could be a Nylander replacement. Bunting you can bring back on a cheap deal using some salary relief from Nylander. Ilya Samsonov you can re-sign on a cheap, short-term deal to pair with Joseph Woll or Erik Kallgren. Matt Murray you likely need to buyout or move.

It may feel tough to keep running it back with this core. You don't have much of a choice. You aren't winning without Matthews/Marner/Nylander so you need to find the right leaders to get you to the next level. O’Reilly helped get you to the second round. It makes sense to try and bring ROR back along with adding a few more veterans to keep Matthews and Marner on track.

If the Leafs can make a few savvy moves and remain patient (which is tough in Toronto), this thing should at least turn into a trip to the East Final or Cup Final in the next few seasons. Matthews and Marner are too good not to get over this hump eventually. Giving up on the core would be a mistake. Retool, get some more experience, solidify the blue line and continue to develop the goaltending. That's the key to the offseason for the Leafs.