Brendan Shanahan said he wouldn’t rush to hire the next general manager of the Maple Leafs.
But let’s be honest, Shanahan will rush to hire the next general manager of the Maple Leafs. He left himself no choice after opting not to bring back Kyle Dubas.
Why? There are a million things to do!
We’ve narrowed down the priorities for the next GM of the Leafs into 10 buckets.
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Let’s dive in.
1. Decide who’s coaching the team next season
In the simplest possible terms: Is it Sheldon Keefe — or not? Without Dubas around, the answer is very likely not.
Keefe has a sterling regular season record with the Leafs. In fact, only Oilers’ coach Jay Woodcroft (.683) has a better points percentage than Keefe (.678) among active coaches.
Obviously the regular season isn’t the issue here. It’s the Leafs falling flat in the postseason in each of Keefe’s four seasons. Keefe did become the first Leafs coach since Pat Quinn to win a playoff series, but that was followed by a disconcerting five-game loss to the underdog Panthers.
One pretty consistent trend under Keefe is the Leafs struggling to produce offence in the playoffs to the same degree as in the regular season.
Case in point: The Leafs have scored 3.5 goals per game in the regular season under Keefe, but only 2.8 in the playoffs.
It’s the team’s stars in particular who haven’t produced to expectation. Most of those failings should fall on the players themselves, but also on the coach to some degree. What’s a coach for if not to pull out more from his players?
If the new Leafs GM decides to keep him, which again seems unlikely, the organization almost has to extend him — don’t they? Keefe would be entering the final year of his contract. Would the organization really want to go the lame-duck route again, only this time with the head coach?
If they do decide to pivot and move on from Keefe, which seems likely with a new GM coming aboard, the obvious next question is who replaces him. The Leafs probably can’t afford to hand the keys to an untested coach (i.e. assistant coach Spencer Carbery.)
They would need a leader with instant credibility.
Joel Quenneville has the best credentials obviously, but he’s also carrying a lot of baggage and would need commissioner Gary Bettman’s approval to re-enter the league. Peter Laviolette is available after being let go by the Capitals earlier this spring. He won a Cup with the Hurricanes way back in 2006 and has guided two other teams (Flyers, Preds) to the final. Has he lost his fastball? You can be sure that lifetime Leafs fan Bruce Boudreau would want the job, but his recent record, not to mention his playoff record, isn’t all that inspiring.
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Dave Tippett? Claude Julien? Gerard Gallant? Is Andrew Brunette, who briefly ran the Panthers last season, too inexperienced? Probably.
2. Assess market for star trade/make star trade
The next Leafs GM will be in a tough spot on this front.
That person can’t make a trade just to make a trade given the immense talent in question. Moves like that set franchises back big time. But the Leafs also can’t bring back the same collection of stars atop the roster again, not after a fifth straight early playoff exit with Auston Matthews, John Tavares, Mitch Marner, and William Nylander all on board.
The problem? Opposing GMs know all that. They know the Leafs basically have to make a trade and that equals immediate leverage in trade talks.
Whoever is running the show for the Leafs will undoubtedly gauge the interest in Tavares, Marner, and Nylander. (I still don’t see any world in which the Leafs trade Matthews, even one that doesn’t include an extension, which we’ll get to pronto.)
Tavares is a tricky one obviously. He makes a lot — at $11 million on the cap for the next two seasons — and he’ll be 33 in the fall. He can, crucially, decline to go anywhere, what with his no-movement clause.
A contending team might be interested if the Leafs retained money in the deal and attached assets. A bad/rebuilding team could be interested to take on the full deal (maybe?) if the Leafs really make it worth their while with picks, prospects etc.
In which case, it stops making sense for the Leafs.
Could the Leafs make a Tavares trade but also get a helpful player, maybe on a bad contract himself, in return? (My first thought on that was San Jose and Logan Couture, who has an $8 million cap hit. Problem No. 1: Couture has four years left on his contract. Problem No. 2: Couture is 34. So the Leafs would be netting $3 million in cap space for the next two seasons but adding two more problematic seasons after that. So yeah, probably a no.)
And again, there’s Tavares, who won’t be inclined to leave his hometown team to play for a cellar dweller or any other team for that matter in all likelihood.
Which means it’s almost certain that one of either Marner or Nylander moves. And what that decision may boil down to is which path is preferable to the Leafs GM:
- Keep Nylander, pay Nylander, trade Marner
- Don’t pay Nylander, trade Nylander, keep Marner
Nylander can sign an extension on July 1 and you have to assume he’ll be looking for $9 million-plus on a long-term deal. (Word of warning to the next Leafs GM: Nylander’s agent Lewis Gross won’t be pushed around.)
If the Leafs and their new GM don’t want to pay that kind of price for Nylander then he feels like the likelier star to go. But wait, you might say! Wouldn’t he have less trade value than Marner, what with the single year left on his contract? Yes.
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However, it’s reasonable to assume that any team parting with assets to acquire Nylander is a team that wants to be in the Nylander business for the long haul. In other words, that team might well be interested in executing a sign-and-trade with the Leafs, which would obviously help greatly in the return.
That team would be getting Nylander at $6.9 million on the cap for next season, superb value, and years and years after that.
Nylander has a limited no-trade clause that kicks in on Canada Day, so there’s that to keep in mind. However, the Leafs will obviously know what they’re going to do with him and his contract by then.
If they do decide to extend Nylander, Marner would be the piece to move. Which is, well, a big meatball. Marner has a no-movement clause that also kicks in on Canada Day, at which point he’ll have total say on his future.
He’s got two years left at $10.9 million on the cap. He can sign an extension next summer, which will be much larger in size. That’s another part of this conversation: Are the Leafs interested in paying his next contract? Or would they rather pay Nylander instead?
Which player nets more in return: Marner with the two years left on his deal or Nylander in a sign-and-trade? It might still be Marner, the superior all-around player. But you could argue for Nylander too. And that’s what the Leafs will have to explore in trade talks.
Could the Leafs trade both? I suppose, but that feels unlikely.
Part of the conversation for the next Leafs GM should be determining which player they believe will deliver more in future postseasons. Nylander probably has the slight edge from the past few playoffs, but it’s close, what with the value that Marner delivers defensively.
Another part of the conversation: What exactly do the Leafs want in return? Ideally, it’s a talented young forward (ideally, a centre) who can help replace the outgoing production at a lesser price, not to mention other stuff like picks and prospects and maybe even ready-made help on defence.
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Trading Marner might well net even more cap space.
Maybe (likely?) it’s a blockbuster with lots of names involved.
3. Extend Auston Matthews
This one is pretty simple: Get Matthews locked up beyond the coming season. Will Matthews be willing to commit to a GM he just met? A GM who has yet to demonstrate whether he’s got the chops to lead the Leafs in the right direction?
Maybe not. It’s one of the risks (a big one at that!) Shanahan took in walking away from Dubas, who was known, liked, and well respected by Matthews.
Matthews will inevitably claim largest-cap-hit-in-the-league status on his next deal from Nathan MacKinnon, who will take over the top spot from Connor McDavid later this fall ($12.6 million).
How big will that cap number be? And how long can the Leafs get Matthews to commit? His last deal came with an $11.6 million cap hit (which ranked second in the league when it was signed) and lasted only five years.
Will this next one be for five? Three? Two? Is the full eight years even a possibility?
It’s worth keeping in mind that the cap is expected to rise considerably when Matthews’ next deal takes effect.
Here’s a big question: What does the next Leafs GM do if Matthews decides not to sign right away on July 1? What if he wants to see how the year plays out? The Leafs would almost be forced into doing just that. Trade Matthews and well, good luck.
4. Find a way out of Matt Murray’s contract
The risks with the Matt Murray acquisition weren’t hard to foresee.
One element of the trade that brought him to Toronto last summer that always felt underplayed to me was that Murray was signed for two years, not one. It wasn’t just a one-and-done bet, in other words. At the time, the common retort to that was, They can just trade him if it doesn’t work out in year one. No big deal!
What they (whoever they are!) failed to mention was that teams don’t just take your problems for free. They want something in return. The question here is what that something is for one year of Murray at $4.68 million on the cap and $6 million in real money.
Chicago let the Leafs slide down only 13 spots in last year’s draft to take on the final two years of Petr Mrazek’s contract ($3.8 million deal).
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Another problem: Murray has a 10-team no-trade clause. He can dictate his future to some degree, which is how he ended up with the Leafs and not the Sabres last summer.
The Leafs could simply buy out the deal. The cap cost in year one is $687,500 and $2 million in year two. It’s that second year obviously that’s thorny. So, what’s more valuable: Clearing all of it away but parting with an asset of some kind, or eating that $2 million in year two but holding onto the asset?
Is there any way for Murray to return? Hard to see it.
5. Sign Ilya Samsonov
Where the Murray bet backfired, the Samsonov bet paid off.
Now, another contract for the new GM to handle.
What’s a fair price for Samsonov after one strong season? What’s too risky for the Leafs?
Evolving Hockey’s top projection: A four-year deal with a cap hit of $5.1 million. That feels like wayyyyy too big of a commitment for a goalie with Samsonov’s resume. Keep in mind: Samsonov has never started more than the 40 games he got into for the Leafs last season.
He was just OK in the playoffs, too, better than Andrei Vasilevskiy in Round 1, to his credit, but worse, by a lot, than Sergei Bobrovsky in Round 2. He finished with an .898 save percentage in nine starts.
Samsonov is a restricted free agent, so the Leafs hold most of the leverage here. I say most because Samsonov has arbitration rights. (His qualifying offer is $1.8 million.)
A one-year deal probably makes the most sense for both parties. For the Leafs, it’s insisting on Samsonov proving he can do it again. For Samsonov, it’s proving he can do it again with a huge payday, as a reward, next summer.
One question I’ve been pondering: What’s the likelihood of Samsonov repeating last season’s performance?
6. Sign other pending free agents
The Leafs have a lot of UFAs to consider before July 1. (They could obviously sign any of those players after free agency begins, but it’s unlikely.)
Who should their GM bring back? My quick thoughts…
- Noel Acciari: Yes, for the right price.
- Zach Aston-Reese: Yes, for a similar price as last season ($840K).
- Michael Bunting: No. Too costly (unfortunately).
- Justin Holl: No. It feels like it’s time to move on.
- Erik Gustafsson: No.
- David Kämpf: Yes, for the right price. (EH projection: $2.1 million cap hit on a three-year deal. That would intrigue me, but I suspect Kämpf’s camp will look for more.)
- Alex Kerfoot: No. It feels like it’s time to move on.
- Ryan O’Reilly: No. Age/injury/foot speed all concern me, especially for the likely price tag/term.
- Wayne Simmonds: No. His NHL days are likely over.
- Luke Schenn: Yes, for the right price/term.
7. Address captaincy (or not)
Another monster Sugo-sized meatball for the GM to ponder.
Tavares has been the captain for the last four seasons. He’s as professional as they come. (The most professional player that I’ve come across.) He’s well-respected. He’s from Toronto. He was the first big star to come home. And yet, sometimes a change is necessary.
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Or not.
That’s what the next GM is going to have to determine here. Whether breaking with the past after years of playoff failure also means breaking with the past version of leadership. It’s a symbolic thing, because the Leafs obviously aren’t winning or losing based on who’s wearing the C.
What’s a little tricky about the whole symbolic change thing is the Leafs would be affixing the C to someone else in their current leadership group: Matthews or Morgan Rielly in all likelihood.
One is the team’s best player — and what better way to celebrate a new contract than by giving him the C? The other is the team’s longest-serving player and culture setter who just delivered a superb playoff.
How would Tavares feel about having the captaincy taken from him? Unprompted, he brought up just how much he cherishes the role after the end of the season.
8. Upgrade the defence
The Leafs ended up with only one reliable pairing in the playoffs, and it wasn’t the one they were probably expecting. It was Rielly and it was Schenn, the two No. 5 overall picks of the organization.
The other combinations, to varying degrees, just weren’t all that good.
Upgrading is going to be crucial for the new GM.
Jake McCabe especially was exposed in a top-four role. He’s under contract for next season, and the one after that, at just $2 million on the cap. Perfectly reasonable coin for a No. 4/5 defenceman. Maybe the Leafs and their new GM (and coach?) envision him with Timothy Liljegren on their third pair next season. Or maybe they try to squeeze him into the top four again, at least to start.
Regardless, the front office should be eyeing at least one meaningful upgrade in the top four. That someone should be better than McCabe and should be able to chop it up with T.J. Brodie opposite top competition in the playoffs. (That role was too much for McCabe.)
Maybe they get that player via the aforementioned star trade. Or maybe they pick one out on the free-agent market. I’ve circled three names that could conceivably fill the bill: Dmitry Orlov, Damon Severson, and Vladislav Gavrikov.
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All of them are bound to be overpaid to some degree, but each would fit, to varying degrees, the kind of role the Leafs need to fill this offseason.
Schenn returning to play with Rielly would cross off the other hole in the top four.
One other thing for the Leafs to consider is what next season looks like for Mark Giordano, who will turn 40 in the fall. The end tends to come hard and fast for older players, and that’s how it looked for Giordano in the playoffs.
The Leafs will have to enter next season knowing Giordano won’t be part of their top six in the postseason. But what about the regular season? Can he be the No. 6 until more help is acquired? Or, does he become a part-time player in the No. 7 role?
9. Fill out the rest of the roster
Some needs will be resolved by trade, others by signing the team’s current UFAs, and others from free agency. The Leafs will have the cap space to go in whatever direction they choose.
Matthew Knies will be a full-time NHLer next season. So will Joseph Woll. The Leafs are probably banking on Bobby McMann and Nick Robertson claiming spots at training camp too.
However they go about it, the Leafs will need to find a No. 2 centre who will push Tavares over to the wing permanently. They’re also likely going to be in the market for a No. 3 centre, assuming O’Reilly and Kämpf both depart, as well as at least one third-line winger (though maybe they give McMann or Robertson that early opportunity).
We mentioned the needs on defence. Sam Lafferty will need some help on the fourth line too.
All of which is to say, this roster is going to look a lot different next season.
10. The draft
The Leafs currently have the No. 28 overall pick and … wait for it … picks in the fifth and sixth rounds. Exciting!
Who knows, maybe that first-round pick gets moved. Or maybe the Leafs acquire more picks in whatever star trade they end up making. Maybe it’s on draft weekend that a blockbuster like that goes down.
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The offseason has barely begun and already it’s been franchise-changing. It was only the beginning. The next Leafs GM has a lot to do and almost no time to do it.
— Research courtesy of Cap Friendly, Evolving Hockey, and Hockey Reference.
(Top photo of Auston Matthews and Mitch Marner: Dan Hamilton / USA Today)
