The Toronto Maple Leafs have missed out on Kiefer Sherwood, as he was dealt to the San Jose Sharks on Monday. The Maple Leafs were reportedly in on Sherwood but ultimately felt short and did not have an offer to entice the Canucks. Sherwood was the top player on the market heading into the Trade Deadline. This is the second trade in two days that the Maple Leafs have missed out on one of their targets.
🔀 Welcome to San Jose, Kiefer Sherwood.
— San Jose Sharks (@SanJoseSharks) January 19, 2026
The Sharks have acquired the forward  from the Vancouver Canucks in exchange for San Jose’s second-round selections in 2026 and 2027, and defenseman Cole Clayton.
Following Sherwood, the trade market for a top-six forward significantly shrinks. What makes the Maple Leafs' missing out on Sherwood more disappointing is the price that the Sharks paid. The Sharks gave up two second-round picks and a prospect. This is something that the Maple Leafs could afford. The good news with the trade is that Sherwood did not get dealt to a divisional rival or a team that is in the hunt for the playoffs, trying to make a big splash.
Potential acquisitions leading up to the trade deadline
For Brad Treliving, he will need to begin to think outside the box because if he is serious about improving the roster, he will need to begin making trades as soon as possible. Potential forwards that can hit the trade market soon are Jonathan Marchessault, Steven Stamkos, Artemi Panarin, and Nazem Kadri. Each of these forwards would be a massive help for a Maple Leafs team that is trying to make a serious run at the Stanley Cup. The problem now stands is the assets they will likely need to give up. The Maple Leafs do not have prospects or draft capital to work with. The Maple Leafs can't afford to trade for a rental, at least not at this point in the season.
The next few months will be an interesting time for the Maple Leafs as the management team has a lot of decisions to make in the near future. Missing out on Sherwood was crucial, but there is still enough talent out there to seriously improve your roster.
