Should Mike Grier pay up and keep Kiefer Sherwood, or is it better to part ways?

SAN JOSE – Kiefer Sherwood has been with the San Jose Sharks for over a month, and there’s little question he likes where the team is headed.

“There are a lot of things that are trending in the right direction, a lot of young players here that have bright futures,” Sherwood told Bay Area News Group late last month. “I love the energy and the joy and the fun that they have.”

Now, with just a few days left before Friday’s NHL trade deadline, it’s just a matter of how much longer Sherwood and some other pending unrestricted free agents will be in San Jose.

Sherwood was acquired by the Sharks on Jan. 19 from the Vancouver Canucks for two second-round draft picks, including one this year. Since then, he’s gotten to know the city and the organization, and appears open to staying with the team long-term.

But Sherwood’s camp and the Sharks still have not come to terms on a contract extension, leaving open the possibility that general manager Mike Grier will seek to flip the Ohio-born winger before the deadline rather than risk losing him for nothing this offseason.

Sherwood, before being acquired by the Sharks, was reportedly seeking a longer-term contract worth more than $5 million per season. A hard-nosed, elite forechecker not shy about getting under the skin of his opponents, with a scoring touch to boot, Sherwood checks a lot of boxes for the Sharks.

“He kind of fits the identity of what we want to be as a team,” Grier said in January of Sherwood. “He’s what this team needs, as far as someone who plays with some sandpaper, some grit, some speed, some physicality.”

But if Grier and the Sharks were amenable to Sherwood’s contract wishes, one would think that by this point — with a bit of give-and-take – that a deal would be done or at least near the finish line.

Instead, a report last week by Pierre LeBrun of The Athletic noted that the Sharks “are open to the possibility of flipping Sherwood,” if they are unable to get him signed before Friday’s trade deadline.

Perhaps this should not come as major news.

Asked in January about the possibility of flipping Sherwood in the event of a contract impasse, Grier didn’t totally dismiss the idea, saying, “If someone calls, maybe I’ll listen and see what they have to say or if they want to make an offer. But his acquisition was a targeted acquisition.”

So, as long as Sherwood remains unsigned, when does Grier start taking those calls on Sherwood and listening, if he hasn’t already?

The way this season has unfolded, with the Sharks being just three points out of a playoff spot in early March, has been a bit of a surprise to the team’s upper management. Improvement over back-to-back last-place finishes was expected in 2025-26, but the belief was that a playoff spot was more realistic for 2026-27.

Basically, San Jose is ahead of schedule by a year.

With that said, does it make sense for the Sharks to hang onto Sherwood for the final six weeks of the season if no extension is in place? The Sharks are still building and not in a ‘go for it’ type window.

It might be a challenge for Grier to recoup the value of the two second-round picks he spent to get Sherwood, but trading him might be the more practical option rather than keeping him for one playoff push.

Grier also has to consider whether spending the cap space allocated to Sherwood, who will turn 31 at the end of March, can be better used elsewhere, particularly on the back end with only two defensemen signed past this season. If the Sharks part ways with Sherwood, they could then pivot to finding a forward with similar attributes.

For his part, Sherwood isn’t delving too deeply into his contract status.

“We’re just focused on playing here,” Sherwood said, adding that his agent, Judd Moldaver, “will give me an update when he gets an update, and I trust him. I’m just focused on playing the game. More than anything, I’m just excited to get in with the group and continue building towards our identity and pushing here in the second half.

“The focus here is just taking care of our home ice here and giving us a sniff to get in the playoffs.”

Sherwood has only been able to play four games with the Sharks after he missed over three weeks with an upper-body injury. In those games, Sherwood has played on the Sharks’ top line – with varying degrees of success – but he does not have a point, as he’s taken four minor penalties, to go with 23 hits and 14 shots on goal.

In the second period of the Sharks’ 2-1 overtime win over the Winnipeg Jets on Sunday, coach Ryan Warsofsky moved Sherwood off the line with Macklin Celebrini and Will Smith to one with Alex Wennberg and Philipp Kurashev. The Graf-Celebrini-Smith line connected for the tying goal early in the third period.

It’s unclear where Sherwood will line up for Tuesday’s game against the Montreal Canadiens, but the coaching staff remains enthusiastic about what the forward brings.

“I think he’s playing pretty good hockey for us,” Warsofsky said. “He’s given us what we’ve asked him to do: get into people and be around the net. I think he probably wants to score a little bit, he has a knack to score, and then they’ll start going in.

“Anytime there’s an adjustment, when you get traded in the middle of the season to a new team, you want to perform. He’s just trying to adjust, and we’ll help him along the way. He’s playing really well. We really like the player a lot.”

The feeling is mutual. But will business get in the way of a long-term relationship?