NHL's Biggest Free-Agent and Trade Disappointments So Far

Buyer’s remorse is a nasty feeling.

As the NHL season hits the quarter-mark, there must be plenty of franchise’s feeling the sting of summertime deals they hoped would be blockbusters akin to The Odyssey but end up flopping like Digger.

Sure, things may change over time, but here are the biggest bombs so far.

Goalie Sergei Bobrovsky and defenseman Darren Raddysh, Toronto Maple Leafs

Maple Leafs general manager John Chayka knew he was rolling the dice by signing via free agency Bobrovsky to a three-year, $21-million contract and Raddysh to an eight-year, $68-million pact after acquiring him for a late-round draft pick.

Bobrovsky’s game had shown signs of deteriorating, and a rebound at age 38 seems unlikely. He has surrendered at least three goals in his past six games, and the Maple Leafs must admit their chances are better with Anthony Stolarz receiving more starts.

As for Raddysh, the buyer beware sign was not just on, it was flashing after his offensive explosion last season, a 22-goal, 70-point season with the Tampa Bay Lightning. After 20 games, Raddysh has only one goal — which came in Tuesday’s clash — and 12 points.

Defenseman Bowen Byram, Chicago Blackhawks

Hoping to boost his team’s rebuild, Blackhawks GM Kyle Davidson dealt the fourth overall pick in this year’s draft, as well as a second round selection, plus depth defenseman Louis Crevier to the Buffalo Sabres for the offensively talented Byram and fourth-line forward Jordan Greenway.

Byram was signed to a six-year, $75-million extension that kicks in after this season.

Unfortunately, injuries have limited Byram to only six games this season, in which he has just one assist. Maybe the Blackhawks will be a Stanley Cup contender in the back half of Byram’s contract, but the hill is steep for the floundering organization.

Right wing Pavel Dorofeyev, New York Rangers

After missing the playoffs for a second consecutive season, the Rangers acquired Dorofeyev from the Vegas Golden Knights for a pair of first-round picks, as well as a third-round selection and then signed him to a seven-year, $77-million contract.

Dorofeyev, who scored 37 goals last season and 35 in the 2024-25 campaign, has six goals and 12 points in 20 games so far. He is also a team-worst (by far) minus-18 rating.

Defensemen Darnell Nurse and Jacob Trouba, San Jose Sharks

The Sharks are well off the pace of a playoff team, and whether you measure by traditional or advanced metrics, they are receiving little payoff from their two highest paid defensemen — who are both signed through the 2029-30 season.

Right wing Valeri Nichushkin, Columbus Blue Jackets

Yes, it was a Colorado Avalanche salary dump that sent Nichushkin to Columbus for a trio of draft picks, the highest being in the second round. Nichushkin’s cap hit is $6.125 million on a deal through 2029-30, although the actual dollars over the final four seasons is significantly less than the first four.

Even so, the Blue Jackets were hoping to get a player worth 25 or more goals, but he has tallied only twice for the offensively starved club currently last in the Eastern Conference.