Maple Leafs Miss Out as Canucks Trade Sherwood to Rival Team

Despite strong interest from Toronto, Kiefer Sherwood is headed to San Jose in a deal that could reshape the market ahead of the trade deadline.

The NHL trade market is starting to warm up, and the Vancouver Canucks just made a move that could have ripple effects across the league - especially for a team like Toronto that’s been lurking in the rumor mill. On Monday, the Canucks sent forward Kiefer Sherwood to the San Jose Sharks in exchange for defensive prospect Cole Clayton and a pair of second-round picks, one in 2026 and another in 2027.

Let’s break this down.

Vancouver cashes in, San Jose adds grit and goals

Sherwood, 30, has been one of the more intriguing names floating around trade circles this season. He’s not a superstar, but he’s the kind of player who can tilt the ice with his effort and physicality.

In 44 games, he’s tallied 17 goals and six assists for 23 points - solid production for a middle-six forward - while throwing a whopping 210 hits and logging over 17 minutes of ice time per night. That’s a physical presence with scoring touch, and it’s not hard to see why teams were interested.

San Jose, a team looking to build momentum and identity, adds a hard-nosed winger who can contribute immediately. Sherwood brings playoff-style hockey to the regular season, and that’s something you can’t teach. He’ll slot in nicely on a Sharks squad that’s trying to turn the corner, and doing so in-division gives this deal a little extra spice.

Vancouver’s return: Eyes on the future

For the Canucks, this is about building for what’s next. Cole Clayton is a name to watch.

He’s not a household one yet, but he’s a promising defensive prospect with upside, and Vancouver clearly sees him as a piece of their long-term puzzle. Add in two second-round picks - both valuable assets in today’s NHL - and GM Patrik Allvin walks away with a package that fits the team’s broader vision.

This is the kind of trade that balances present value with future potential. Sherwood was producing, yes, but Vancouver leveraged that production for a return that could pay dividends in a few years. It’s a smart play from a front office that’s been carefully managing its cap and prospect pool.

What it means for the Maple Leafs

Now, let’s talk about the team that didn’t make the move: the Toronto Maple Leafs. Sherwood had been linked to Toronto for months. He checked a lot of boxes - physical, productive, affordable - and losing out on him stings, especially after also missing on Rasmus Andersson, who was shipped to Vegas.

But here’s the silver lining for Toronto: the price.

Vancouver didn’t get a first-round pick in the deal. That’s important.

It sets a market that might work in Toronto’s favor. If a player like Sherwood - who’s having a strong season - goes for a couple of second-rounders and a prospect, then maybe Toronto doesn’t have to empty the vault to make a meaningful addition.

Let’s say they pivot to a bigger name like Dougie Hamilton. Yes, he’s a defenseman, and yes, his cap hit is a different animal altogether, but the framework is there. A package built around a 2026 third-rounder, a 2027 second-rounder, and a prospect like William Villeneuve or Ben Danford could be enough to get New Jersey’s attention - especially if the Devils are willing to retain some salary or take back a contract to make the math work.

That’s a big “if,” of course. Hamilton has term left on his deal, and retention complicates things. But if the market continues to soften, Maple Leafs GM Brad Treliving might find himself in a better position than expected to swing a deal that upgrades the blue line without mortgaging the future.

Looking ahead

For now, Sherwood heads to San Jose with a chance to make an impact on a team trying to climb. Vancouver adds future assets and a young defenseman to their pipeline.

And Toronto? Well, they’re still in the hunt - and the way the trade market is shaping up, they might be able to land their target without paying a premium.

The deadline is still a ways off, but the chess pieces are starting to move. And if this Sherwood deal is any indication, we’re in for an intriguing few weeks ahead.