Auston Matthews, New York Islanders, Toronto Maple Leafs, William Nylander

Islanders Have Nylander Trade Opportunity with Matthews Extension Done

The big news in the NHL this week was the Auston Matthews extension. The Toronto Maple Leafs signed him to a four-year, $13.2 million per year deal that makes their best player the highest-paid in the NHL.

The extension prevents Matthews from entering free agency and testing the market. But it also puts the Maple Leafs up against the salary cap, most notably after this season when the contract kicks in. As a result, the clock is ticking on their other star, who will be a free agent in the 2024 offseason, that being William Nylander. The Maple Leafs can keep Nylander on the roster for the season ahead, but it’s unlikely they will keep him long-term, and it could prompt them to trade him at some point.

Related: Maple Leafs Sign Auston Matthews to 4-Year Contract Extension

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A lot of teams will be interested in acquiring Nylander, and the New York Islanders are no exception. However, the Islanders and general manager (GM) Lou Lamoriello will have a handful of obstacles to overcome in order to land the star forward, and a deal would require a lot of moving pieces.

Islanders’ Cap Situation Creates Obstacles

The Islanders don’t have a lot of cap space to work with. Heading into the 2023-24 season, they are $486,625 above the cap and will have to send at least one skater down to the American Hockey League (AHL) before the season begins. Next offseason, the Islanders will have an even tighter cap situation with goaltender Ilya Sorokin’s eight-year, $8.2 million per year extension starting to take effect. To add Nylander and subsequently extend him with a contract in the $8 million or more per season range, the odds are stacked against them to add a player of his caliber.

That said, the Islanders will have room next offseason to work with. The biggest help will be Cal Clutterbuck and Matt Martin coming off the books. The two veteran forwards departing will provide the Islanders with $3 million to work with. It’s a good start, but Lamoriello will have to make a trade one way or another to free up the remaining cap space to a player of Nylander’s caliber.

William Nylander Toronto Maple Leafs
William Nylander, Toronto Maple Leafs (Jess Starr/The Hockey Writers)

The two skaters that come to mind are Jean-Gabriel Pageau and Brock Nelson. Otherwise, the Islanders only have two other skaters that have a $5 million cap hit or greater but don’t have no-movement clauses attached to them, Mathew Barzal and Kyle Palmieri. The bottom line is that every player who can be traded to make a move possible plays an integral role on the current roster, with Nelson and Barzal being two of the team’s best players. Lamoriello would likely avoid trading any of the above-mentioned skaters, but it would be the cost of adding Nylander and worthwhile to consider with that in mind.

The two skaters to watch would be Pageau and Palmieri, as they can free up $10 million in cap space if they are both traded. The question is which teams would be interested in adding either forward. Both are still playing at a high level but are in their 30s, an indication that they will only be able to play at this level for so long. The teams that could acquire both skaters are the Maple Leafs and other contending teams that would want to add a veteran scorer to their forward unit.

When a Nylander Deal Can Likely Occur

The Maple Leafs will look to make a push with their core to win the Stanley Cup this year. They advanced to the Second Round in the 2023 Stanley Cup Playoffs and have the pieces in place to make a deep playoff run and win the first Cup title since 1967. With the team looking to make a run with this core, Nylander, at the very least, will stay on the team until midseason.

This creates an avenue for the Islanders to make a move at the 2024 trade deadline. It’s unlikely the Maple Leafs will trade away one of their best players, especially since they are projected to be one of the top teams in the Eastern Conference, but a deal is still possible.

William Nylander Toronto Maple Leafs
William Nylander, Toronto Maple Leafs (Photo by Mark Blinch/NHLI via Getty Images)

The other option the Islanders have is to wait until free agency and acquire Nylander without having to make a trade with the Maple Leafs. This is the ideal route for them, but unfortunately, Lamoriello has noticeably avoided making splash signings in free agency. Every offseason, the expectation is that Lamoriello will sign a star scorer to a big contract, but five years into his Islanders tenure, he has yet to do so.

In 2019, Artemi Panarin was available, but he signed with the New York Rangers. In 2022, Johnny Gaudreau and Nazem Kadri were available, but Gaudreau signed with the Columbus Blue Jackets, while Kadri signed with the Calgary Flames. In the past offseason, Alex DeBrincat was placed on the trade block but went to his hometown team, the Detroit Red Wings, in a blockbuster trade.

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Lamoriello’s track record points to a Nylander trade being more likely, but a lot would need to swing in the Islanders’ favor. For starters, the Maple Leafs must stumble out of the gate and look awful a few months in. Likewise, the Islanders would need to be near the top of the Eastern Conference. Lastly, Lamoriello has to have a favorable offer in place early in the season to sway the Maple Leafs to move Nylander.

The Asking Price for Nylander

When the Islanders acquired Bo Horvat from the Vancouver Canucks, they had to move on from three pieces, specifically, an NHL-ready player, a top prospect, and a selection in the first round of the NHL Entry Draft. The package ended up being Anthony Beauvillier, Aatu Raty, and their 2023 selection in the first round. The Maple Leafs are a contending team and not a rebuilding one, so the pieces will be different, but the asking price, in terms of value, would be similar.

Bo Horvat New York Islanders
Bo Horvat, New York Islanders (Amy Irvin / The Hockey Writers)

The NHL-ready players this time would have to be Pageau and Palmieri. Unlike Beauvillier, both skaters are older and starting to decline. However, both forwards are playoff-proven and can put a team looking to make a Cup run over the top. Instead of a top prospect, the Maple Leafs will look for a defenseman to round out their unit, specifically, a left-side defenseman to help out Morgan Rielly, Jake McCabe, and Mark Giordano. The defensemen who would likely be involved in a deal would be Sebastian Aho and Samuel Bolduc, two younger skaters who can add speed and youth to the defensive unit. Pair a veteran skater and a young defenseman with a draft selection in the first round, and GM Brad Treliving, who is in his first year with the team, might make the deal.

A deal would be a risky one for both teams. Lamoriello doesn’t want to part with the players on the current roster, especially Pageau, while the Maple Leafs would hope to play out the entire season with Nylander on the team. However, a blockbuster trade can be beneficial to both sides and set them up for a Cup run next season and success in the long haul.

Nylander’s Long-Term Value on the Islanders

Nylander is entering the prime of his career and hitting his stride after scoring a career-high 40 goals and 47 assists. He would become a core part of the Islanders’ top six and help transform their offense into one of the best in the league. Specifically, he’s a versatile forward who can both create scoring chances with quick passes and find the back of the net himself with a great shot. Last year in the playoffs, the Islanders’ lack of versatility was on full display, as the offense scored only 15 goals against the Carolina Hurricanes in the six-game series.

Horvat would have another playmaker on his wing along with Barzal. Likewise, Anders Lee, who is an instinctive goal scorer, could have Nylander on his other wing, finding him open in the offensive zone. If Nelson remains on the Islanders after the trade is completed, he can be the ideal playmaker for Nylander with his playmaking ability.

The Islanders have a fair share of obstacles in their way to land Nylander. However, the Matthews extension creates a path for Lamoriello to do so. Ideally, they wait until the summer to add him, but if a favorable deal is in place, the Islanders and Maple Leafs can make the splash of the 2023-24 season.

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