Three NHL players face pivotal seasons amid contract and performance questions
Darren Raddysh, Jason Robertson and Brayden Point are under pressure to prove their worth in the 2026-27 campaign.
Three NHL players are facing pivotal, make-or-break campaigns in the 2026-27 season, with general managers raising questions around big-money risks and uncertain futures.
Darren Raddysh, 30, is signed to an eight-year deal that makes him the Toronto Maple Leafs’ highest-paid defenceman and is having to manage life-changing expectations in his hometown.
One concern is how the Leafs plan to deploy Raddysh on a pairing with Morgan Rielly.
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“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.”
The concern is whether the player Toronto committed to for eight years is the same one who broke out with the Tampa Bay Lightning last season.
John Chayka’s first and biggest bet as general manager of the Leafs has a real probability to blow up in his face.
Jason Robertson is expected to sign a long-term extension to stay with the Dallas Stars shortly after he is first eligible on Jan. 1.
That would solve a temporary salary cap crunch for the Stars, where Tyler Seguin’s expiring money essentially slides to Robertson’s raise.
For Robertson, there is injury risk on a one-year deal, though that is mostly covered by personal insurance.
His risk is also mitigated by the rising cap environment, as even if his production reverts to around 33 goals and 80 points, close to $15.6 million might be the market rate.
The bigger danger for Dallas is if Robertson overperforms, hits 100 points again, and climbs to a stratosphere they cannot afford, allowing him to walk to free agency with nothing in return.
Sources indicated both sides remain on amicable terms despite reported trade talks with the Seattle Kraken, leaving the door open for a long-term deal.
Perhaps only Stars GM Jim Nill could have successfully repaired that relationship, though skepticism will remain until Robertson’s next contract is signed.
Brayden Point, after an inexplicable season with 18 goals and 50 points, is at a crossroads on the wrong side of 30.
Over the previous three seasons, Point averaged 46 goals and 90 points, had two Stanley Cup rings and was a lock for Team Canada.
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 and that parts of his game need to change.
One observation was that Point seemed a half-second slow arriving to pucks to get shots off and his timing was off, which might have been fixable with a full summer of training.
One prominent Western Canadian agent likes to say that adversity always resets the best players.