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  • Writer's pictureHWH

Call Me Crazy, but Here’s Why an Erik Karlsson to Toronto Trade Makes Sense

Have you gotten the loud boos, the yelling and the sneers and jeers out yet? For this proposal, you'll have to get into an even more open-minded space than that. If you're a fan of the Sharks you'll have to remove the typical gut-reaction of a superstar trade. The initial thought that your best player, your potential Norris-winning defenseman is worth multiple firsts, a team's best prospect, and 2-3 other high quality pieces. In a vaccuum, yes. In NHL23 with the cap turned off, yes. In the NHL in 2023, no.

If you're a Toronto fan, you're going to have realize that you're going to give up something, and recognize what is needed organizationally at this specific juncture. A Karlsson trade, something which is extremely complex to manage for a multitude of reasons, laid out by my colleague at San Jose Hockey Now Sheng Peng here, will require lots of finessing, and needs to fit for the player and both organizations. Let's start with the player first.

Why A Karlsson Trade To Toronto Makes Sense For Karlsson

Well, this is it right? This is the peak of the mountain for Karlsson. He's an exceptional player, who just put up his best season statistically in his career, and the best for a defenseman in 30 years. He also did this on an absolutely horrible Sharks team, who had the least amount of wins in the NHL. Sadly the Sharks get to pick 4th instead of 1st, despite that low mark.

Either way, San Jose isn't going anywhere anytime soon. A recent meeting between Erik Karlsson's agent and San Jose management confirmed that all sides agree on a trade this summer, despite some quibbling, squabbling, waffling and wavering during the season about this specific point. The wheels have officially been set in motion, and Karlsson will be traded in the near future.

So at age 33, with 4 years left on an 11.5 million AAV contract, Karlsson is going to want to be traded to a team that is Not competitive 3 years from now, not on the border of being competitive, not were competitive, not could be competitive with Karlsson. This is an important distinction in my opinion. Karlsson, to maximize his utility to a team, needs to be traded to a cup contender to really push for his chance of winning a cup during his outrageously expensive contract. He also owns a fancy full no-movement clause with that contract, so a team must be the right team for Karlsson to consider waiving for a trade.

The issue obviously, is that teams generally don't have the cap to acquire Karlsson's caphit, and still be competitive to win a cup. Teams are finagling RFA contracts, or utilizing LTIR to maximize every dollar. It's a huge reason why the deal wasn't finished in the trade deadline timeframe. Teams like Vegas were interested, but couldn't find the way to make the cash work. Enter Toronto. The ultimate contender with a finite window, stars galore on the roster, and the desire to shake things up. A perfect destination for Karlsson. So why does it make sense for Toronto, and what could they be giving up?

Why A Karlsson Trade to Toronto Makes Sense for Toronto

I'm not here to tell you Toronto fans things you don't know, or make fun of you about the failures your team has had during the Matthews era. If it makes you feel any better, it hasn't been any more fun as a Sharks fan these past few years, despite you guys winning a whole lot more. What I am here to tell you, is that Erik Karlsson is a superstar level defenseman, who you can acquire for not-superstar level prices (read: keep Matthew Knies), who can help you win a Stanley Cup within the next two years.

The competitive window here is the most important thing. After next season Toronto has expiring contracts in William Nylander and Auston Matthews, both who likely get raises. After 2 seasons, Mitch Marner and Tavares drop off as UFAs. The timeline tight. Unless one of these four are traded, which doesn't seem to be the indication at this time. Despite repeated playoff failures, Toronto seems to want to run it back. The issue? TJ Brodie and Matthew Murray.

$9.6875 million dollars in AAV for 2023-2024, in two players who perform at or below replacement level play. It's only for one year, but it's an important year for Toronto's cup aspirations. The going rate for dumping that level of money? It's a first or more, as this chart from The Athletic's Harman Dayal shows:

If we add up to near $10 million in dumping, it's likely a 1st and another pick. Wouldn't it make sense to turn that first round pick into I don't know...a 100 point defenseman, instead of I don't know....nothing? That's the initial point I'm trying to make here. San Jose has the space and the desire to eat those contracts for this year. Toronto has the desire to jettison them, probably for nothing. Why not involve Karlsson to make it palatable for both sides?

The second thing Toronto needs this offseason is cheap and good forward depth.

(That's so many red UFAs, wow. I wonder if a team could fill in some holes for Toronto in a trade or something)

You know what San Jose has lots of? Cheap and good forward depth. Forwards that are sort of just doing well in San Jose with no real purpose other than being eventual trades. San Jose could help ease the burden of a Karlsson trade, not only in the removal of Murray and Brodie's contract, but also by providing cheap, above replacement level scoring as a sweetener. But what about San Jose? Why does it make sense for them? They seem to be giving an awful lot to fulfill this trade request, what's in it for them?

Why A Karlsson Trade to Toronto Makes Sense for San Jose

This is definitely it. The end of the Doug Wilson era came hard and fast, crashing the team to depths we have not seen in a few decades. Despite his miraculous season, nothing could save the slow decline of the Sharks into terribleness.

Karlsson needs to be traded while he has value as a 100-point defenseman. For awhile there, it was looking like a buyout, a miraculous LTIR, or watching a worn-out Karlsson skate around until the heat-death of the universe were our only options for the future. Now, a trade is on the horizon, and anything we get for Karlsson I'll feel right as rain about.

There's the immediate aspect of not having two NHL goaltenders signed for next season as well that makes sense in the above deal. The Sharks will be looking for one this offseason, and being paid to take Murray just makes too much sense. It might even make sense for Murray as well, giving him an opportunity to own the net in front of a...shaky...Kahkonen.

The Sharks have oodles of bottom six forwards who contribute, but will be leaving as UFAs in the near future regardless of what happens.

The Sharks have expressed an interest in not retaining a significant portion of Karlsson's salary, which may be the only hiccup here, but I believe it is manageable. Let's get into the proposal.

The Proposal

This trade is essentially net neutral for Toronto for the next season, while upgrading a 15 point TJ Brodie to a 100 point Erik Karlsson. Keep in mind, the next season is the most important season for Toronto, the last year of Matthews and Nylander making their current rates before raises. It's also, hopefully, one of the last "cap-crunch" seasons for the league, with the COVID-19 flat cap era expiring. This will help ease the burden of the now $9.5 million Erik Karlsson contract heading into the next offseason.

Steven Lorentz is an excellent fourth liner for $1 million. Svechnikov and MacDonald are replacement level depth that give Toronto some contracts and actual NHLers for next season. Toronto loses no impact roster players, keeps their most important prospect in Knies to develop or trade in another deal.

Now keep in mind, the 1st, 3rd, 5th and 5th are over multiple drafts, and the going rate for getting rid of Toronto's cap problems is already close to the above value, with nothing coming back, nevermind a Norris-worthy defenseman and valuable depth.

Ty Voit, Fraser Minten and Dennis Hildeby are the prospects that make the deal worth it for the Sharks. Mid-level for sure, but could develop into players for San Jose going forward.

The End of An Era in San Jose

So while Toronto fans might grit their teeth at losing three prospects and four draft picks, the reality of the team's cap situation, expiring deals, and a willingness to go all-in, makes this trade a possibility. If you're a Toronto fan and you're reading this, how mad are you going to be when the 2023 1st+ is traded to like Arizona for the Leafs to dump Brodie and Murray for absolutely nothing vs. the trade above? Because that might just happen.

While San Jose fans might whine about not getting a true stud prospect, more firsts, or even a better first for Karlsson, this is a trade that has to happen. This might just be the best deal San Jose can get at 2 million retention, a number which GM Mike Grier seemingly wants. San Jose needs a goaltender, has the space to weaponize their cap into multiple picks and prospects, and finally put an end to the Doug Wilson era by trading Karlsson to Toronto.

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Lots of good points in this. I've long thought taking back other team's bad contracts is a valuable part of a deal and the Sharks should capitalize on this. The Flyers GM said he's now in that biz, too.

But first, the problem. The Leafs players mentioned have NMC's, which make it difficult.

Its not just Toronto. Seems NMCs of various sorts have been handed out like candy on larger deals. Getting guys to waive to come to San Jose will be difficult.

Next, as you point out, cap space has value. I've used a rule of thumb that $10mil of cap space is worth a 1st rd pick. Retaining 1/2 on EK65 does a lot more than retaining $2mil.

Replying to

I think bold is the way to go here. There are plenty of friction points (different sort of deal, NMCs ,etc), but if the trade is this -- you get a Cup and I get 5 1st rounders -- that is a trade most GMs make. Especially if you fear someone else might make that trade which is a huge obstacle to your own Cup hopes.

I mentioned I put out a trade scenario with the Bruins. Logan/EK65, 50% retained which likely works. If you're Toronto, are you going to let that happen or will you be in the mix? Boston is win right now (who knows how many more seasons Bergeron wants before he calls it a career and…


Uncle Damfee
Uncle Damfee
Jun 21, 2023

This was brilliantly written, and makes absolute sense. Thank you so much for giving us a good article to dream of. I would take this deal with a huge smile on my face. Who knows? Maybe Murray can turn his career around!

Jun 22, 2023
Replying to

Thank you for reading! Yeah there's also a chance Murray stands on his head and then he can be flipped to a contender at the deadline.


It’s starting to bug me, losing Erik Karlsson but I’m accepting of it. I have no real idea of the young guys coming back but I’ll cheer them on. The draft capital could really excite me. I say, “git ’er done.”

Jun 20, 2023
Replying to

Just got to get it done unfortunately. Picks and prospects coming back in any way make this worth it for me.

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