Top 5 Worst NHL Free Agency Contracts 2025: Overpay Debacles (2026)

The NHL's free agency period has been a whirlwind of activity, with teams splashing cash on big-name players and fringe NHLers alike. But amidst the excitement, there are some contracts that stick out like a sore thumb. These are the deals that have raised eyebrows and sparked debate among fans and analysts alike. From overpays to questionable acquisitions, these are the top five worst contracts signed by UFAs since July 1.

The Byram Blunder

The Chicago Blackhawks made a bold move by trading their fourth-overall draft pick for Buffalo Sabres defenseman Jake Byram. But the real head-scratcher came when they signed him to a new deal kicking in for 2027-28. While Byram had a career-high 42 points last season, he's not in the same league as Minnesota Wild defenseman Quinn Hughes or Colorado Avalanche blueliner Cale Makar. The pressure is now on Byram to deliver, and the Blackhawks's playoff hopes hang in the balance. This contract could become an albatross before it ends.

Greer's Golden Goose

Florida Panthers GM Bill Zito traded AJ Greer's signing rights to the Anaheim Ducks in exchange for Radko Gudas. Greer, a 29-year-old with career-highs of 17 goals and 32 points, is being paid nearly $5 million. While he had a breakout year for Florida, his production pales in comparison to his new salary. Greer is a worker bee who'd be very valuable at $2 million per season, but at more than double that amount, he feels like an anchor for Anaheim.

Kane's Comeback?

The Blackhawks also signed Patrick Kane to a $16-million contract. Kane, now 37, posted 16 goals and 57 points in 67 games with the Detroit Red Wings last season. While he still has good hockey left in him, the Blackhawks's overpay smacks of desperation. At a time when other teams are locking up their young stars, Chicago's hometown discount for Kane turned into the opposite. The Hawks may come to regret this deal.

Sissons' Salary

The Toronto Maple Leafs signed Colton Sissons to a $4.25-million contract. Sissons, a 32-year-old with six goals and 11 points in 66 regular-season games with the Vegas Golden Knights, feels like a move that could've been addressed internally. Many legitimate Stanley Cup contenders are paying their top-six forwards handsomely, leaving the rest of the change to their bottom-six forwards. Sissons could stick out financially if Toronto finds itself in another sour situation like last year.

Trouba's Troubled Turnaround

The San Jose Sharks acquired 32-year-old Jacob Trouba, whose game has regressed in recent years. Trouba had a decent season with the Ducks last year, putting up 10 goals and 35 points in 81 games. But at the cost San Jose paid for him, Trouba isn’t likely to be a great-value addition. He can mentor the Sharks' youngsters, but other than that, Trouba isn’t a difference-maker.

These contracts are a reminder that free agency can be a double-edged sword. While teams are eager to lock up their stars, they must also be cautious not to overpay or make questionable acquisitions. As the NHL season unfolds, these deals will be watched closely, and their impact on the teams and players involved will be closely scrutinized.

Top 5 Worst NHL Free Agency Contracts 2025: Overpay Debacles (2026)

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