Rejoice hockey fanatics, for the start of NHL free agency is almost upon us.

Come July 1 at noon (ET), the league’s landscape for the 2024-25 season will begin to take shape as this summer’s various restricted and unrestricted free agents land new contracts and potentially new teams.

And while the overwhelming majority of signing announcements this off-season will involve players who are free agents as of present, we can expect at least a handful of them to involve those who are actually still under contract. Because, also beginning on July 1, any players heading into the final season of a multi-year contract become eligible to sign an extension.

If we zero in on that specific group, we find there are some major names in the mix. Three in particular that stand out: Leon Draisaitl, Mitch Marner and Igor Shesterkin.

Why these three? Well, as was just established, each of these high-impact NHL superstars is about to enter into the final season of the contracts they signed with their current teams, which will leave them as UFAs upon expiry in 2025. And, more interestingly, despite the unique circumstances surrounding each of their individual futures, they all have the potential to reset the financial market for their respective positions — with Shesterkin being a goaltender, Marner a winger and Draisaitl a centre (though, yes, we know he plays a good chunk on the wing).

Considering the salary cap increase of $4.5 million for the 2024-25 season (setting the upper limit at $88 million) and the expectation that it will maintain a similar climb in subsequent years, the league finds itself heading into some uncharted territory when it comes to the amount of money star players will be able to command moving forward.

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Now, before we get too ahead of ourselves, it is worth remembering there is a chance that none of Draisaitl, Marner or Shesterkin ink a new deal in advance of their current one expiring. But, in all three situations, the team — be it the New York Rangers, Toronto Maple Leafs or Edmonton Oilers — and their star player can decide to get a new deal done this summer to avoid said player becoming a UFA next summer and potentially testing the market. One would think each of those teams is relatively motivated to avoid that happening. Though, you never know.

From a player’s perspective, meanwhile, there are likely additional variables to consider when making the personal decision of signing an extension or not, and if the decision is yes, what that extension then looks like. We will delve deeper into those variables by examining the current situations of Draisaitl, Marner, and Shesterkin individually.

Mind you, we will be discussing a lot of hypotheticals here. As these three players near extension eligibility, the lone statement we can make with near certainty is to not expect any of them to take a discount.

So, keeping that in mind, here’s a look at what these contract extensions could look like and what they would mean against an increasing salary cap.

Leon Draisaitl, Edmonton Oilers
Age: 28 (UFA at 29)
Current contract: Eight years, $68 million ($8.5 million AAV)
Time of signing: August 2017
Cap hit percentage at time of signing: 11.33

With a player of Draisaitl’s calibre, it’s safe to assume that most of the power rests in his hands. You afford yourself a certain degree of freedom and flexibility when you are a perennial 40-goal, 100-point scorer. If he feels staying with the Oilers is what's right for his future, the team will likely be happy to accommodate in order to keep him and superstar teammate Connor McDavid together.

According to a recent report from Frank Seravalli of Daily Faceoff, the Oilers have already begun discussions with Draisaitl’s camp about a new deal. A good sign all around — but the question with Draisaitl is how much he will push his limit.

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If he extends this summer, there is a chance he will become the league’s highest-paid player in terms of average annual value, regardless of whether on a short- or long-term deal. If so, that would likely only hold true until his aforementioned superstar teammate, McDavid, comes up for an extension the following summer.

On another eight-year deal, Draisaitl would comfortably lock in for the long term based on what he has shown the Oilers — and everyone else — he is reliably capable of. If he opts to go the four-year route, like Auston Matthews, he would leave room for another potentially hefty contract at the age of 32. The inherent risk involved there is if his production considerably slows over the next few years, future earning dollars from a long-term deal could have been left on the table. In other words, Draisaitl would be betting on himself, which seems like a reasonably safe thing to do.

Honing in on numbers specifically for Draisaitl, we can conceivably place him in the $13-14 million AAV neighbourhood with the rising salary cap. If we look at recent signees at his position that also became the highest contract in the league at the time, the ball-parking gets a little easier. Matthews signed his four-year deal last summer, which carries a AAV of $13.25 million and accounted for 15.87 per cent of the Maple Leafs’ cap at the time of signing. The previous summer, Nathan MacKinnon signed an eight-year extension with the Colorado Avalanche. With an AAV of $12.6 million, that contract took up 15.27 per cent of the team’s cap. And when McDavid signed his eight-year, $100 million contract in 2017, the ensuing $12.5 million AAV was an impressive 16.67 per cent of Edmonton’s cap.

This is why it feels reasonable to believe that whether Draisaitl signs a four- or eight-year contract extension, he could pull in somewhere around $14 million per year, or more. This would account for at least 15.9 per cent of Edmonton’s cap at the time of signing — and 15.2 per cent in the first year of the contract should the cap rise by another $4 million as projected.

Mitch Marner, Toronto Maple Leafs
Age: 27 (UFA at 28)
Current contract: Six years, $65.4 million ($10.903 million AAV)
Time of signing: September 2019
Cap hit percentage at time of signing: 13.38

When it comes to Marner, there’s a lot less confidence at present about the player’s future with his current club. Will the Maple Leafs look to trade their multi-talented — yet sometimes maligned — star winger? With a no-move clause in hand, Marner has full control over whether or not he allows Toronto to send him elsewhere.

Predictably, the ever-voracious NHL rumour mill suggests several teams would be greatly interested in obtaining the services of this impactful offensive forward. In the case that Toronto was to receive an offer that they felt made sense and Marner could be sold on, we would probably see some kind of sign-and-trade take place.

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“Mitch controls a lot of this whole thing,” Treliving told Pierre LeBrun of The Athletic earlier in June. “If there’s a way to make our team better, we’re going to do it. But we’re certainly not going to make a trade just so we can pound our chest and say, ‘Look, we’re different.'”

So, if a trade doesn’t happen, there are two other straightforward ways for this to play out. Either the Maple Leafs ultimately choose to extend him at some point, maintaining their core, or Marner stays in Toronto, finishes out the remainder of his contract and then departs in free agency next summer.

While speculation looms about the potential of his future with Toronto, what remains largely unclear at this point is what Marner actually wants. You would assume the hometown guy would hope to stay, but maybe he would prefer a fresh start somewhere under less market and media scrutiny considering the heat he’s been subject to.

With the possibility the Maple Leafs and Marner could still come to an agreement on an extension — though maybe not the most likely outcome — the first place to look for a comparable contract is that of his teammate and fellow winger, William Nylander.

Nylander signed an eight-year, $92 million extension with the Maple Leafs this past January. His $11.5 million AAV made up 13.77 per cent of the team’s cap at the point of signing. If we stick to that percentage for Marner on the upcoming $88 million cap, he could be looking at just over $12 million, which would then account for 13 per cent of a $92 million cap the following year.

But does Marner want more? If he went to a team — either via trade or free agency — that didn’t already have so much money tied up in a handful of star players then perhaps he could command an even larger raise from his previous contract.

Igor Shesterkin, New York Rangers
Age: 28 (UFA at 29)
Current contract: Four years, $22.67 million ($5.66 million AAV)
Time of signing: August 2021
Cap hit percentage at time of signing: 6.95

After examining two forwards, it’s time to discuss the goaltender in the mix. Once established by Carey Price and Sergei Bobrovsky, could Shesterkin be the next netminder to set a new bar for No. 1 goalies? It seems quite likely.

The 2022 Vezina Trophy winner’s performance over the past several seasons has clearly set him up to be the highest paid goaltender come his next deal. As per Mollie Walker of the New York Post, “there’s reason to believe that Shesterkin’s camp is aiming for as high as $12 million a year.”

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While some teams would balk at the idea of tying up that much money in a goaltender, even if they are a starter, maybe the Rangers won’t. Maybe the back-to-back Stanley Cup Final appearances by the Florida Panthers has proven it can be a worthwhile investment. Bobrovsky is currently in the fifth year of a seven-year, $70 million contract with a $10 million AAV. And that contract has received its fair share of criticism at times.

Shesterkin’s own performance in this year’s playoffs — leading the Rangers to the Eastern Conference Final — only served to solidify his value to the team. His fan-favourite status with the Big Apple faithful certainly doesn’t hurt either. It seems if it were up to them, Rangers fans would be telling management to pay Shesterkin whatever he wants, as his popularity has only continued to grow amongst the strongly opinionated and vocal group.

Bobrovsky signed his contract as an unrestricted free agent in 2019, and at that time it accounted for 12.27 per cent of Florida’s cap. Price’s eight-year, $84 million extension with the Montreal Canadiens in 2017 accounted for 14 per cent, with an AAV of $10.5 million, while Andrei Vasilevskiy’s eight-year, $76 million extension with the Tampa Bay Lightning in 2019 was only 11.66 per cent of the cap, with an AAV of $9.5 million. If Shesterkin is seriously targeting a $12 million salary, that would account for 13.6 per cent of the team’s cap at the time of contract’s signing and 13 per cent of a subsequent $92 million cap. In that context, maybe it does make a bit of sense…

Yes, signing a goaltender to a long-term deal, especially one with a double-digit AAV, is undeniably risky business. Shesterkin is approaching his 30s and some natural regression with age isn’t out of the realm of possibility. But as of right now, he is a player they simply need in order to remain a contending team. Taking on that kind of risk might be the price they have to pay in order to avoid any kind of riff that could lead the netminder to pack up his talents and try out free agency instead.

When speaking to the media at the conclusion of the Rangers’ season, Shesterkin jokingly replied, “I’m sorry, I don’t speak English,” when asked if he would be considering a long-term contract.

Regardless of how long his extension ends up being, if it does see him make $12 million per year or any amount close to that, he’ll be doubling his previous salary and establishing a new league ceiling for the position. Can you really ask for better than that?

To summarize the long-winded thoughts above in the simplest terms available: Draisaitl, Marner and Shesterkin are going to get paid — a lot. It is inevitable. And against a rising cap, they could all begin to reset the post-pandemic market.

*All salary and cap information obtained via CapFriendly

Three major contract extensions that could be signed this off-season

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