It’s looking more likely by the day that Kiefer Sherwood’s time in San Jose could be coming to a quick end as we approach the deadline.
According to Pierre LeBrun of The Athletic, “ A league source told me this week that the Sharks are open to the possibility of flipping Sherwood if they can’t get him signed.” “Whatever the case, I get the sense that the first contract-extension conversation was a real wires-crossed moment as far as expectations from both sides.”
The Sharks acquired Sherwood back on January 19th from the Vancouver Canucks for their own 2nd-round picks in 2026 and 2027. A lot to give up for a pending UFA, but also showed that the Sharks were likely willing to extend Sherwood.
To this point, an extension hasn’t happened, and with the Sharks currently out of a playoff spot, it doesn’t make much sense to hold on to the asset without recouping some value. Sherwood is still cost-controlled, with just a 1.5 million cap hit, and plays a physical, playoff-friendly game that contenders will pay for a playoff run. While the Sharks likely won’t get full value back, they could still recoup a pair of 2nds from a contender, albeit most likely way later in the 2nd round.
An extension would be preferable, but if Sherwood's ask is in the 5-6 AAV range on a 4-5-year deal, as has been speculated, the Sharks would be smart to steer clear. Sherwood brings value to the lineup, but at the end of the day, this is his only season scoring above a 20-goal pace with a rather unsustainable shooting percentage; his offensive profile has regression written all over it. On top of that, while it has only been 4 games, Sherwood has not been a seamless fit into the Sharks' lineup, getting demoted from Celebrini’s wing numerous times in the midst of games.
It will be an interesting story to watch in the coming days, but it looks like Grier has gotten himself in a bit of a mess with the Sherwood trade. It will be interesting to see how he chooses to resolve it.