The Pittsburgh Penguins are having a miserable season in 2024-25. As they tumble toward the Eastern Conference basement, the NHL trade deadline looms as an important date. While they have publically said they are not trading Sidney Crosby and Evgeni Malkin, everyone else should be on the table. The difference between the Penguins' dream and nightmare trade deadline scenarios is how much they sell.
Through Monday's action, they have 58 points in 63 games, second-worst in the Eastern Conference. General manager Kyle Dubas has already stocked the cupboard full of draft picks, with five extra selections already secured. They got a first-rounder back for Marcus Pettersson and Drew O'Connor, who both went to the Vancouver Canucks after the JT Miller trade. Is there another first-rounder hiding on their roster?
The Penguins have to sell to give Crosby and Malking any chance at another playoff run. But how much can they realistically move on from this year?
Dream scenario: The Penguins add another first-rounder

If somehow, someway, the Penguins could get another first-rounder at the trade deadline, it would be the dream scenario. They already picked up one, a top-ten protected pick from the New York Rangers. None of their pending free agents will yield one, although they should all be on the move as well, so it would take a core piece.
Rickard Rakell is near the top of all of the big trade boards heading into Friday's trade deadline. He is due $5 million annually through 2027-28 and has a modified no-trade clause. If a contender was willing to give up a first-round pick for the former Anaheim Duck, Dubas has to take that deal. He will likely break his career high in goals this year, so the price will be high.
Erik Karlsson is another player the Penguins could send out for a high-value return. A first-rounder may be rich for a 34-year-old with two more years left but combining him with a rental could net a first. Even in these scenarios, the rentals have to be on their way out. Matt Grzelcyk, Anthony Beauvillier, Emil Bemstrom, and Ryan Shea are those pending free agents.
Nightmare scenario: There are still free agents on the roster after Friday
The Penguins should not have a single pending free agent on their team by Friday at 3:01 p.m. While none of those players will land them a big prospect or top pick, the assets have to be moved. The mid-round picks could be where they draft the next stars of their team and keeping Anthony Beauvillier won't have that impact.
Kyle Dubas took this job knowing he had to handle the final years of Sidney Crosby and Evgeni Malkin. That was never going to involve trading either one of those stars and was always going to be a long process. The Penguins are far from competitive and may never be with the Hall of Famers on the roster. Selling pieces is the only chance they have.
That puts the pressure on Dubas to draft well in the coming years. Many of his Maple Leafs draft picks have not made the NHL yet, with Matthew Knies being the lone exception. The Penguins have to hit on their picks this year and develop them quickly to give Crosby young talent to work with.
There is no excuse for the Penguins to have a single free agent on their roster on Friday. They should be tanking and hoovering up draft picks to quickly rebuild for the veterans on the roster. If they can get another first-round pick, then great, but anything is positive at this point in their rebuild.