Anyone who knows anything about hockey will know that Nikita Kucherov is one of those rare players GMs would struggle to properly compensate for in a direct swap. He's in such rare air that any compensation package to keep Tampa Bay in contention this year would require more than one player to step up and make up for all the production he brings to the table.
This is a guy who has accumulated over 500 points over the last four seasons and is only 15 points shy of McDavid over that span. But teams like the Maple Leafs have an advantage here because they know that 1) he'd reportedly be open to joining the and 2) time isn't a luxury Tampa Bay has.
Some background: Nikita Kucherov, 33, has made it public that he will not return to Tampa Bay next season and has also formally requested a trade, while making it public that he is looking for a $20 million AAV, six-year deal in the offseason. Nylander, 30, is locked up for the next five years at nearly half that amount ($11.5 million AAV).
"It's time to move on."
— Daily Faceoff (@DailyFaceoff) November 5, 2026
Dan Milstein on Nikita Kucherov's future in Tampa Bay.
Catch the full interview on DFO Insider. @JeffMarek | @TheFourthPeriod
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🍎: https://t.co/lc8bpUiysr
📺: Coming Soon pic.twitter.com/8CODrcx1Q5
When factoring in their value, it's important to not simply consider what they've done in their careers so far or how they've fared amongst their peers, but also what they will cost a team against the cap, and how an organization expects their output to grow, stagnate, or decline based on the player's age, ability, and circumstances.
This exercise breaks down each player's calibre and, based on the current landscape and the situation's vulnerabilities, assesses whether a swap of sorts would suit the Toronto Maple Leafs and the Tampa Bay Lightning.
Now, let's get into it.
Accolades and Records
Nikita Kucherov
Thirteen NHL seasons, 893 games played, 1,144 points, 405 goals, 177 career playoff points (16th all-time), 2x Ted Lindsay Award winner (2019, 2026), 2x Hart Trophy winner (2019, 2025), 3x Art Ross Award winner (2019, 2024, 2025), 2x Stanley Cup champion (2020, 2021), 7x All-Star, all-time points leader for the Tampa Bay Lightning.
He joins Wayne Gretzky, Mario Lemieux, and Jaromír Jágr as the only players in NHL history to win at least two Stanley Cups, Hart Trophies, Ted Lindsay Awards, and three Art Ross Trophies. He is only one of five players in NHL history to record 100 assists in a single season. He's notched six 100-point seasons and four 40-goal seasons over his 13-year career.
William Nylander
Twelve NHL seasons, 767 games played, 712 points, 302 goals, 58 playoff points, 1x All-Star, 1x IIHF World Championship Gold Medalist & Tournament MVP (2017)
Nylander currently ranks sixth in franchise goals, eighth in points (and will likely enter the top 5 by season's end), and is the fourth-fastest player in franchise history to reach 300 career goals. He has three 40-goal seasons under his belt and hit a career-high 98 points in 2024–which he is on pace to surpass this season.
Point for Kuch.
Salary Comparisons
Cale Makar just signed the highest-paid contract in NHL history at $163,200,000 ($20.4 million AAV over 8 seasons), and it kicks in next season. He's 27, has established himself as the league's most talented defenceman, and is a 2x Norris Trophy winner and Stanley Cup champion. Since making his NHL debut in 2019, he's led all defencemen in points and goals and has done so despite never having played a full 82-game season, and the wildest stat of all is that if you included the points accrued from defencemen during the 2018/19 season (the year before Makar entered the league), he would still be leading all defencemen in both goals and points over that span. It's an excellent deal for a player still only scratching the surface of his prime and will keep him under contract through his late twenties and early thirties. It's a deal Colorado had to make and one they surely won't regret.
Macklin Celebrini also just signed an extension that kicks in next season, making him the league's second-highest-paid player at an AAV of $18.8 million over 5 years. Perhaps the most talented player in the league under 21 years of age, he broke out last season, scoring 45 goals and accruing 115 points at 19 years old–the third most points scored by a teenager in NHL history behind Wayne Gretzky and Sidney Crosby. If you're San Jose, it's a very safe bet to lock up your now-captain and face of the franchise at any cost, and this one feels like a bargain.
Nikita Kucherov
We're assuming Kucherov, a man who rarely backtracks on his beliefs and is as stoic and headstrong as they come, won't settle for anything less than $20 million AAV or the term he wants on a six-year deal. Several teams are positioned to wait out this in-season drama and have the cap space next year to give him that exact number and term while keeping the books balanced with an ever-growing salary cap. If this is solely about money and term, then there's no reason to believe teams desperate for a star forward will shell out the dough and term to lock up the reigning MVP.
There's no question that Kucherov is in the highest echelon of NHL players (that is, if you believe anyone can be in the same tier as McDavid) and deserves to be paid as such. The question isn't whether Kucherov will get that contract; it's whether he will be worth it in the second half of the term if his contract extends beyond his age-36 season.
Nikita Kucherov has reached 20 points ✅
— PaceBall (@paceball__) November 4, 2026
Season Stats:
4 Goals | 16 Assists | 20 Points
Pace: 23 Goals | 94 Assists | 117 Points#GoBolts pic.twitter.com/hGTCmzgzcy
According to statmuse.com, only two players have surpassed the 100-point mark after the age of 35. Joe Sakic did it in 2006 at 37, and Gordie Howe put up 103 points at 40. That isn't to say Kucherov couldn't join the likes of Sakic and Howe, or that he couldn't still be an effective 1st-line RW capable of putting up north of a point per game, keeping him securely in the top 20 point getters. The expectation, however, for $20 million a season will be to hunt Art Ross Trophies.
Far too often, aging superstars are given legacy contracts that extend well past their prime, leaving teams handicapped in the number of moves they're capable of making to improve their roster–ask Leafs fans how they feel about having to pay Carolina to take the Patrick Marleau contract off their hands; Seth Jarvis would have been an awfully nice piece to this team. Kucherov's $20 million salary would put him among the NHL's elite for the remainder of his contract, which implies he'll remain among the league's top scorers for that duration. If Tampa paid him that sum, one could argue the six-year term would reflect respect for the services and accolades he's brought to the franchise, and nobody would bat an eye. Similar to what the Blackhawks did for Toews and Kane, it was the right thing to do given what they gave that franchise, although look at how that played out after their final Cup run. If you're a separate organization looking only to the future, the risk you incur on those last few seasons is very real. There's no question that a 3-year, $20 million contract is worth Kucherov's services, and if a fourth year would get a deal over the hump, and a team was positioned to make it happen, it would be hard to fault any GM for taking that shot.
William Nylander
Since Nylander's first 30-goal campaign in the 2019/20 season, he trails only David Pastrnak in goals scored among right wingers and ranks eighth league-wide. Since signing his new extension in 2024, Nylander is a top-20 points scorer and top-10 goal scorer across the league–his AAV is tied for 17th most expensive as of this season. That situates Nylander where he's been expected to perform. With a new wave of extensions kicking in next year and players getting paid more with every passing day, Nylander, in the thick of his prime at age 30, is signed through the most productive years of his career. It's a deal that will get more and more cap-friendly with every passing season and is tied to a player currently on pace to break his single-season goal-scoring record.
William Nylander has reached 10 goals this season
— PaceBall (@paceball__) November 1, 2026
Season Stats:
10 Goals | 11 Assists | 21 Points
Pace: 51 Goals | 56 Assists | 108 Points#Leafs pic.twitter.com/mgigviIcZh
A top-6 right-winger in the echelon of bona fide first-liners (though line configuration plays a role in his deployment) who will score 35 goals and 80 points in his sleep and rarely misses games comes with a price tag that fairly reflects that output and availability. And with the cap growing, it gives a team like the Leafs the opportunity to forgo the prospect of bolstering their forward corps and instead redirect their attention solely to the backend, which, this season more than in past, is in dire need of some juice.
For the reasons that Nylander is still tapping into the heights of his prime and that his contract offers the team more cap flexibility moving forward, to not only re-sign Matthews, but also give the organization a chance to allocate that additional money towards parts of the roster that need more help, it's a point for Nylander.
Toronto's big-swing philosophy & Tampa's vulnerability
On the other side of the Nylander saga are his defensive deficiencies, his questionable work ethic, and his inescapable tie to an era of Leafs hockey that has left many Leafs fans bitter over a lack of deep playoff success. Chayka has no such ties to that era, and his sympathies clearly run thin in what was already a massive organizational overhaul this offseason on and off the ice. When opportunity comes knocking, Chayka opens the door and invites it in for a seat at his table.
Kucherov is certainly the better player, and most would expect his points output to surpass Nylander's for at least the next couple of seasons. Whether Kucherov will remain in the MVP conversation every year for the next six years seems unlikely, and although he may have a few big years left, it's difficult to imagine many 100+ point seasons in the second half of the six-year pact he's looking for. What can be expected, though, are leadership qualities, big-game pedigree, a spot alongside Matthews, a top-5 power play in the league, and a mentor for a young Gavin McKenna whose game is awfully comparable. Although Nylander holds a no-move clause in his contract, it seems reasonable to think he would waive it to be coached by Jon Cooper and run out his five-year deal in the Sunshine State, competing for Stanley Cups with a reputable organization like the Lightning.
For a team like Toronto, which is firmly in the win-now window, competing in the most difficult division in hockey, and trying to sway Matthews into re-signing long-term, their only priority is continuing to build a roster capable of contending for a Stanley Cup; there's a sense that any move that would improve the roster's likelihood of winning right now would be worthwhile. And although another scoring winger is hardly one of the Leafs' biggest priorities, if there's a trade that offloads additional cap and is, at its core, a direct Nylander-Kucherov swap, it feels likely that Chayka would be licking his lips at the opportunity to bring in a player of Kucherov's calibre. Extending him beyond this season and making the cap work with Marchenko's new $12.5 million deal kicking in next season will probably mean offloading some veteran contracts and bringing in some younger players on ELCs, but it's a challenge that Chayka would no doubt take on if it meant bringing two MVPs together.
As for Tampa, they may have to come to terms with the reality of watching the reigning MVP and their all-time franchise points leader walk out the door for nothing. It's a harsh reality to face, and there are few opportunities to replace some of that output with a player who would not only be a direct positional swap but who has also established himself as one of the league's premier RWs, and who supposedly plays on a team that is on Kucherov's wish list. It's a swap that could save Brisebois money under the cap for next season and buy him additional time to keep Tampa's win-now window open.
