NHL Insider Frank Seravalli Names Three NHL Players Facing Make-or-Break Seasons

Pressure. Every professional hockey player faces it. But three NHL players in particular are facing pivotal, make-or-break campaigns in 2026-27, with GMs raising questions around big-money risks, uncertain futures and whether past performance can be rediscovered.

Darren Raddysh, Toronto Maple Leafs

John Chayka’s first and biggest bet as general manager has a real probability to blow up in his face.

Raddysh is already 30. He’s signed to an eight-year deal that makes him the Leafs’ highest-paid defenseman. And he’s having to manage life-changing expectations in the sport’s biggest pressure cooker, which happens to be his hometown.

Yet my biggest concern might be how the Leafs plan to deploy Raddysh: on a pairing with Morgan Rielly.

“My thing is, I have no clue what Darren Raddysh is,” one NHL GM said. “Did he find something at age 30 or was he a massive benefactor of Nikita Kucherov and some unsustainable finishing? This feels like an unprecedented ascent, like he won a lottery ticket.”

The GM continued, “He’s a solid player with a nice shot, but the unprecedented nature of his path and age would make me feel pretty nervous.”

In other words, the concern isn’t whether Raddysh can play, it’s whether the player Toronto has committed eight years to is really the player who broke out in Tampa Bay last season.

It feels like Raddysh is the ultimate boom or bust. This is either the beginning of a beautiful story or the first scenes of eight nightmarish years.

Jason Robertson, Dallas Stars

The smart money is on Jason Robertson signing a long-term extension to stay in Dallas shortly after he’s first eligible on Jan. 1.

That would solve a temporary cap crunch the Stars had this season, one moment in time where Tyler Seguin’s expiring money essentially slides to Robertson’s raise. But that isn’t without risk — for both Robertson and the Stars.

For Robertson, there is of course the injury risk on a one-year deal, covered off mostly by personal insurance. But his risk is also mitigated by the rising cap environment. Even if his production reverts back to the last two seasons — around 33 goals and 80 points — close to $15.6 million might be the market rate.

The bigger danger for Dallas is what happens if Robertson overperforms. If he hits that 100-point mark again, he might climb to a stratosphere they can’t afford in their cap structure and walk to free agency with nothing in return.

Sources indicated both sides remain on amicable terms despite the reported agreed-upon trade to Seattle.

That’s significant because there doesn’t appear to be any lingering damage from the trade talks, leaving the door wide open for Robertson and Dallas to find common ground on a long-term deal.

Perhaps only Jim Nill could have successfully repaired that relationship — though there will remain a healthy dose of skepticism until Robertson’s next contract is signed.

Brayden Point, Tampa Bay Lightning

From the moment he was cut from a bantam team because of his size, Brayden Point has had a raging fire burning inside to prove he belongs.

Over the previous three seasons, Point averaged 46 goals and 90 points, had two Stanley Cup rings and was a lock to play among the most decorated players on Team Canada.

Now, after an inexplicable season with 18 goals and 50 points, Point is at a crossroads. He’s on the wrong side of 30. How will he respond?

My biggest takeaway was that Point did not pull punches at his end-of-season availability, refusing to blame his outlier season on injury or excuses. He acknowledged that what worked before might not work now.

That self-awareness matters. Point doesn’t seem to view last season as something he can simply write off; he knows there are parts of his game that need to change.

To me, Point seemed a half-second slow arriving to pucks to get shots off. His timing was off. That might have been fixable with a full summer of training.

One prominent Western Canadian agent likes to say: “Adversity always resets the best players.” We’re about to find out.