SAN JOSE – With the San Jose Sharks in playoff contention for the first time in seven years, general manager Mike Grier faces some new – and difficult – questions over the next several weeks before the NHL trade deadline in March.

Chief among them: If the Sharks remain in the playoff hunt leading into the deadline, should Grier trade some of his pending unrestricted free agents if a tempting offer comes along? Or, if contract extensions can’t be reached, keep them for the stretch run, and potentially risk letting them walk away in the summer for nothing?

“That probably would be the probably toughest decision I’ll probably have to make (before) the deadline, is trying to figure that out,” Grier said Thursday at SAP Center. “Where the group is at, where the team’s at, what’s the best decision for the group short term, but also long term. If there’s a deal out there that gets presented to me that makes sense, it’s something that our group up top is going to have to really think about and consider.

“But if we’re going well and things are good, and we decide that we just kind of roll through it and see what happens, it’s something we’re prepared to do.”

Among the Sharks’ pending UFA are forwards Kiefer Sherwood, Jeff Skinner, Ryan Reaves and Pavol Regenda, defensemen Mario Ferraro, John Klingberg, Timothy Liljegren and Vincent Desharnais, and goalie Alex Nedeljkovic.

Grier said he acquired Sherwood from the Vancouver Canucks with a long-term view in mind. So while it would be a surprise to see Sherwood, Reaves, Regenda or Nedeljkovic traded on or before the March 6 deadline, there is a bit more uncertainly regarding the defense corps.

Ferraro, whose contract does not have any trade protection and carries a reasonable $3.25 million cap hit, is once again considered one of the NHL’s top trade targets. He’s been a first or second pair defenseman for the Sharks all season and leads the team in blocked shots and penalty killing.

Klingberg, signed to a one-year, $4 million contract as a free agent on July 1 last year, has played much better of late after a difficult start to the season. His contract has a full no-trade clause until Jan. 30, after which it becomes a partial no-trade clause with a 14-team no trade list.

Klingberg had four points in 19 playoff games in the Edmonton Oilers’ second consecutive run to the Stanley Cup Final last season. The year before, Desharnais played 16 games for the Oilers in first run to the final. This year, when healthy, Desharnais has been a physical force and one of the Sharks’ top penalty killers. Liljegren, too, has been steady for the most part.

But subtracting one or more of the pending UFAs, particularly on defense, could hamper the Sharks’ ability to make the playoffs for the first time since 2019.

Due to tiebreakers, the Sharks (25-21-3) enter Friday just outside of a playoff spot. The Seattle Kraken, who hold the second wild card spot in the Western Conference, have 53 points, same as the Sharks and Los Angeles Kings. They are also two points behind the Anaheim Ducks for third place in the Pacific Division.

As a possible comparable, Grier mentioned the situation the Montreal Canadiens were in last season before the deadline.

The Canadiens were three points out of a playoff spot on March 1, 2025, a week before the deadline. They did not buy or sell, and by standing pat, showed faith in the players that they could still make the postseason.

The Canadiens signed one of their pending UFAs, center Jake Evans, to a four-year contract three days before the March 7 deadline. They also kept another pending UFA, forward Christian Dvorak, for the stretch run, and he had 13 points in the team’s final 20 games to help it make the postseason. Dvorak then signed with the Philadelphia Flyers as a free agent.

“So it’s something that’s definitely a possibility,” Grier said of keeping pending UFAs past the deadline. “But that’ll probably be — depending on how the team’s doing — that’ll probably be the toughest or biggest decision out there that I’ll have to figure out.”

The Sharks have six more games, including Friday’s home game against the New York Rangers, before the start of the Olympic break in early February. Once the NHL resumes its schedule near the of the month, the Sharks have just four more games before the deadline.

If the players inside the Sharks’ dressing room want Grier to keep the band together, they can’t afford to let up now.

“This stretch and then coming out of the break is big,” Sharks winger Ryan Reaves said. “Teams really try and position themselves coming into this break, knowing that final stretch is going to be a lot harder. But also, you want to see where you’re at in terms of, are you making trades, are you selling, or what are you doing?

“These next five, six games is a big stretch in a lot of senses. But we want to be in a good position coming out of that break to make a push for spots in the playoffs.”