Penguins’ 3 Worst Contracts Entering 2026-27

A buyout would not be painless either. The Graves buyout structure would stretch the mistake across multiple seasons, and that is the kind of lingering penalty the Penguins should be trying to avoid during a roster transition.

Erik Karlsson’s Contract Still Limits Flexibility

Erik Karlsson is still a productive player, so this is not the same kind of contract problem as Graves. Karlsson had 15 goals and 51 assists for 66 points last season, which remains high-end offensive production from the blue line.

His 2025-26 production is the reason this conversation has to be handled with some balance. The problem is the cap hit and the fit.

Karlsson carries a $10 million Penguins cap hit entering the final year of his deal, and that is a massive number for a team still trying to become younger and more flexible. The Penguins can live with it for one more season, but that does not make it efficient. Pittsburgh needs a clearer defensive structure, and Karlsson’s contract still shapes almost everything the team can do on the right side.

The right side already has Kris Letang, Korczak, and van Riemsdyk. That creates a crowd, and Karlsson’s number makes the group harder to balance. The Penguins’ Karlsson decision has been sitting over the organization for a while because moving him would not be simple, especially with his contract size and control over his future.

Karlsson can still help Pittsburgh, which is why his contract is not the team’s worst. But at $10 million, he has to be more than useful. He has to be a major driver, and the Penguins have to decide whether one more season of that cap hit helps their retool or delays the next version of the roster.

Trevor van Riemsdyk Deal Carries Early Risk

van Riemsdyk’s contract is not a disaster yet, but it carries enough risk to land on this list.

The Penguins signed van Riemsdyk to a two-year, $8 million deal with a $4 million cap hit, and that number is aggressive for a 35-year-old defensive defenseman. His new contract runs through 2027-28, which means Pittsburgh is not only paying for a veteran stopgap this season. It is also carrying the deal into next season.

The argument for the signing is understandable. The defenseman gives head coach Dan Muse another experienced right-shot defenseman who can kill penalties, play lower in the lineup and bring some stability. The Penguins needed more defensive structure, and van Riemsdyk has been around long enough to know what he is.

The issue is price versus role. A $4 million cap hit is a lot if van Riemsdyk settles in as a third-pair defenseman, especially when the Penguins already have Karlsson, Letang, and Korczak on the right side. The van Riemsdyk signing makes more sense if he plays meaningful defensive minutes, but it looks much worse if he becomes another expensive veteran blocking younger or more flexible options.

That is why this deal is more about risk than proven damage. It could be fine if van Riemsdyk gives Pittsburgh two steady seasons. It could also become another example of paying too much for defensive certainty that only looks certain on paper.

Penguins Have to Avoid More Graves-Type Mistakes

The Graves contract is the warning. Karlsson’s deal is the short-term weight. Van Riemsdyk’s contract is the new risk.

That is the lesson for Pittsburgh. The Penguins can live with some inefficient money because they still have flexibility, but the organization cannot afford to keep stacking questionable commitments. This roster is already trying to balance the final years of the Crosby-era core with a younger group that needs more opportunity.

That is why Pittsburgh’s broader trade-board conversation matters. Dubas needs to keep looking for impact talent, but he also has to protect the cap sheet from mistakes that reduce his options. The Penguins need contracts that either produce value now or preserve flexibility later.

Graves does neither at the moment. Karlsson produces, but the cap hit is still heavy. Van Riemsdyk may help, but the contract already comes with questions.

The Penguins’ worst contracts do not completely ruin the roster, but they show why the next few decisions matter so much. Pittsburgh has enough cap room to keep working, enough veterans to remain competitive and enough young players to make the future interesting.

What it cannot afford is another deal that looks like Graves. If that contract keeps aging the way it has, it may not just be the worst deal on the current roster. It could become one of the worst the franchise has ever had.