The Pittsburgh Penguins are entering a season that could determine much more than whether they return to the Stanley Cup Playoffs. Sidney Crosby, Evgeni Malkin, Erik Karlsson, Andrei Kuzmenko, Tommy Novak, and Justin Brazeau are all scheduled to become unrestricted free agents after 2026-27. Their situations cover nearly every major decision facing president of hockey operations and general manager Kyle Dubas, including retirement, extensions, trade-deadline value and creating opportunities for younger players.
The three stars at the top could determine how long Pittsburgh continues balancing short-term competitiveness with its transition toward a younger roster. The other three must prove they deserve to remain part of that transition. Here are the Penguins’ six most important contract-year players, ranked by how much their upcoming decisions could affect the franchise beyond this season.
1. Sidney Crosby
Sidney Crosby remains the clear number one because every part of Pittsburgh’s direction still connects to him. Crosby recorded 29 goals and 74 points in 68 games last season, extending his NHL record to 21 consecutive point-per-game campaigns.
His contract carries an $8.7 million average annual value through 2026-27, and Pittsburgh should have little difficulty affording another one- or two-year agreement if he wants to continue playing. A one-year extension would make Crosby 39 by the end of the deal, but his production and team-friendly cap hit make his desire to continue—not the financial commitment—the more important question.
An extension would allow Dubas to continue building around a competitive veteran core while younger players develop. If Crosby decides to retire, it would accelerate almost every difficult conversation: the argument for retaining expensive veterans would weaken, the pressure to collect future assets would grow, and Pittsburgh’s long transition would become much more immediate.
Crosby’s combination of production and cap value already made him the clear leader among the Penguins’ three best contracts. His next decision will matter far more than the financial terms.
2. Evgeni Malkin
Evgeni Malkin signed a one-year, $5.5 million extension after producing 19 goals and 61 points in 56 games. The official Malkin contract announcement keeps him in Pittsburgh for a 21st season but does not settle whether it will be his last.
Malkin will turn 40 shortly before training camp, so health and role will be as important as production this season. His move to the wing last season allowed Pittsburgh to experiment with younger centers while keeping one of its most talented offensive players in the top six. That arrangement could extend his career without blocking the middle of the lineup.
Another productive season may lead to one more short contract, while a decline or another injury-heavy year could bring one of the most important careers in franchise history to an end. Malkin’s departure would create cap space and a major offensive opening, but it would also remove a player who was above a point-per-game pace last season.
3. Erik Karlsson
Erik Karlsson enters the final year of his contract after delivering his strongest season with the Penguins. He recorded 15 goals and 66 points in 75 games, earned team MVP honors and drove much of Pittsburgh’s offense from the blue line. His performance demonstrated that he can still be a difference-maker, but his age and cap hit complicate what comes next.
Extending Karlsson would preserve Pittsburgh’s most productive defenseman while prospects such as Harrison Brunicke and Owen Pickering continue developing. Letting him leave would create significant cap flexibility but remove the player who led the Penguins with 51 assists last season. A deadline trade could produce assets, although Pittsburgh would have to accept losing an important part of a potential playoff push.

The decision whether to re-sign Karlsson this summer remains unresolved, and this contract year should provide the clearest answer yet about whether he belongs in the next stage of the roster.
4. Andrei Kuzmenko
Andrei Kuzmenko is Pittsburgh’s most obvious short-term performance gamble. He signed a one-year, $5 million contract on July 1 after recording 13 goals and 25 points in 52 games with the Los Angeles Kings last season. The official Kuzmenko signing release emphasized his scoring history and ability to create offense around the net.
The Penguins are betting that he can rediscover part of the form that produced 39 goals during his first NHL season with the Vancouver Canucks. A return to the 20-goal range would help replace some of Anthony Mantha’s lost production and give Pittsburgh several options. Kuzmenko could earn an extension, become a valuable deadline rental or simply provide useful offense for one season.
If his production remains near last season’s level, the deal will look more like a temporary roster patch. This season will help determine whether Pittsburgh continues using one-year contracts to search for scoring or pursues a more permanent solution.
5. Tommy Novak
Tommy Novak produced 16 goals and 42 points while appearing in all 82 games last season. His versatility allowed him to move between center and wing, contribute on special teams and fill different positions throughout the lineup.
Novak’s $3.5 million contract expires after the season, creating a difficult value decision. Pittsburgh acquired him with two full seasons of control, but the second one must clarify whether he is a long-term piece.
A repeat of his 42-point season could make Novak worth extending as a flexible middle-six forward. The concern is whether a larger contract would fit while Ben Kindel, Hendrix Lapierre, and other younger centers push for responsibility.
If Pittsburgh falls out of contention, Novak could also become a practical deadline target for teams seeking affordable secondary offense. His future will reveal how aggressively the Penguins intend to create space for their younger forwards.
6. Justin Brazeau
Justin Brazeau gave Pittsburgh strong value during the first season of his two-year, $3 million contract. He recorded 17 goals and 34 points in 64 games, using his size and net-front ability to provide a different element in the middle of the lineup. The official Brazeau contract announcement confirmed that his $1.5 million cap hit runs through 2026-27.
Repeating that production would make Brazeau an extension candidate, but Pittsburgh must consider the growing competition around him. Kuzmenko, Nicholas Robertson, Egor Chinakhov, and several younger forwards are battling for offensive roles, and Brazeau was not a lineup lock during the playoffs.

That uncertainty could also make him a useful trade chip. The Penguins’ 3 Trade Candidates article focused on more prominent veterans, but an affordable power forward could attract deadline interest without requiring management to dismantle its core.
Penguins’ Contract Decisions Could Accelerate Transition
These six situations divide naturally into two groups. Kuzmenko, Novak, and Brazeau will determine how much of Pittsburgh’s supporting forward group remains intact. Their performances could produce extensions, trade assets or openings for younger players.
The decisions involving Crosby, Malkin, and Karlsson carry much larger consequences. Karlsson’s future could reshape the defense and cap sheet. Malkin’s departure would close another chapter of the championship era. Crosby’s decision could determine whether Pittsburgh continues its gradual transition or finally accelerates toward its next core.
Dubas does not need to resolve every contract before the season. Health, production, and the standings should influence which players remain and which become trade candidates. The risk would be waiting too long and allowing valuable players to leave without receiving anything in return.
The Penguins built flexibility into the 2026-27 roster. This season will determine whether that flexibility supports another playoff run or becomes the tool that finally moves the franchise into its next era.
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