Nick Kypreos has never shied away from uncomfortable conversations in Toronto, and his recent comments on Real Kyper and Bourne reopened one of the most sensitive debates surrounding the Maple Leafs: would the team actually be better off moving William Nylander?
Kypreos discussed a couple of trade ideas that involved the dynamic winger. In one case, he quickly dismissed a trade pitch. In the other, he liked the deal and said he would pull the trigger. They were two distinct trade ideas involving Nylander but both were meant to improve Toronto’s blue line.
One was a high-profile one-for-one swap with Adam Fox. The other involved Seattle Kraken defensemen Brandon Montour and Jamie Oleksiak.
He Said No to The Adam Fox Trade
The Adam Fox concept didn’t pass the sniff test for Kypreos. While Fox was once one of the league’s smartest puck-moving defensemen, the former Norris Trophy winner is no longer what he once was. Kypreos made it clear he wouldn’t move Nylander straight up for him.
He argued that Fox isn’t big, doesn’t play a physically imposing style, and—according to Kypreos—no longer brings the same game-altering presence he once did. Fox’s omission from Team USA is the latest in a run of signs that he’s no longer viewed as one of the NHL’s best. That matters if Toronto is giving up Nylander, a winger who consistently drives offense, creates space, and performs in big moments.
From the Leafs’ perspective, a Nylander-for-Fox swap feels more lateral, maybe even a downgrade. Fox would help the blue line, but he wouldn’t single-handedly fix it. All the while, he wouldn’t replace Nylander’s offensive production.
The Montour–Oleksiak Package Is More Compelling
The second idea was more up his alley. Kypreos suggested Toronto would be better off trading Nylander to Seattle for Brandon Montour and Jamie Oleksiak, framing it as a chance to reshape the Leafs’ DNA rather than simply swapping stars.
Related: NHL Rumors: Bold Nylander Trade, Kadri Move, & Shopping Kotkaniemi
Montour can eat huge minutes, provide offense, has a Stanley Cup pedigree and answers several questions for the Leafs moving forward, as he’s locked into a long-term contract. Oleksiak, while not a centerpiece, adds size, physicality, and depth to a blue line. He can be re-signed for cheap at the end of this season.
This would be the Maple Leafs adding offense and defense on the blue line.
Is Cashing Nylander In Actually Worth It?
It should be pointed out that there is a risk in either trade. Trading Nylander solves one problem but creates another. With Mitch Marner already gone, moving Nylander strips Toronto of another elite offensive driver. Depth can soften that blow, but neither deal brings back a top-six forward and neither replaces the star-level production that leaves. If Toronto makes the postseason, where Nylander has been one of Toronto’s most reliable performers, they’ll miss him.
There’s also the reality of timing. Seattle has little incentive to move Montour, who is viewed as a core piece, and Toronto is back in the playoff race. Making a franchise-altering move while trending upward would be a massive gamble.
This feels less like serious trade talk and more like a philosophical question Toronto may have to answer if the postseason ends in disappointment again: do you keep betting on elite skill, or do you finally cash it in to change the team’s identity?
