NHL · 4 hours ago

Ranking the Biggest Losers and Winners From NHL Free Agency

Grant White

Host · Writer

Loser: Dallas Stars
For years, the Dallas Stars have been knocking at the door. They were runner-ups in the Western Conference Finals in three consecutive years, getting shown the door in the opening round of this year's postseason. Needing to attract some backend talent, the Stars were snubbed by a few noteworthy players.

Zach Werenski demanded a trade out of Columbus, stating his intention to suit up for any team other than the Blue Jackets. The Stars came knocking, and Werenski decided that rotting away on a non-competitive Jackets team was the better option. Moreover, Dallas has over $10 million in cap space to play with, and it couldn't land any of the available defensemen on the opening day of free agency.

Teams in the Central Division and Western Conference are getting better, and the Stars can't even convince a guy who demanded a trade to play with them. The Stars may improve via the trade market, but it looks increasingly unlikely.
Losers: Toronto Maple Leafs
Desperation is a wretched odor. When the rest of the NHL is looking around the room to see who is emitting that pungent smell, the Toronto Maple Leafs will shamefully head for the showers and apply an overwhelming dose of body spray.

To everyone's dismay, the Leafs brought in John Chayka as the General Manager earlier this offseason. Somehow, Chayka is even more disconnected from reality than we thought.

The Leafs made it a priority to target some fringe NHLers and overpay them. Colton Sissons fulfills a bottom-six role, contributing just 32 points and a -23 rating over the past couple of seasons. Previously a $2.8 million cap hit, Toronto saw it fit to pay him $4.2 million for the next two seasons. More confoundingly, Sergei Bobrovsky is set to earn a staggering $21 million over the next three seasons. This, despite the Russian netminder posting a 3.07 goals-against average, .877 save percentage, and -23.4 goals saved above average last season as a 37-year-old.

Of all the blunders the Leafs have made over the years, the 2026 opening day of free agency may go down as one of the worst.

Hopefully Kawhi Leonard pans out for Toronto; the Raptors are the only thing you have to look forward to.
Winner: Sergei Bobrovsky
The Florida Panthers' fall from grace is best encapsulated in Sergei Bobrovsky's demise. The two-time Stanley Cup-winning goaltender hit a wall in 2025-26, as most people anticipated in his age-37 season. Still, he bamboozled the Leafs into paying him $21 million until he's nearly 41.

The laissez-faire netminder is the antithesis to all things Toronto. The Maple Leafs have put themselves at the center of the NHL universe, and Bobrovsky's demeanor gives the impression that he couldn't care less about what happens on the ice. He was brought in to save the Auston Matthews era, but it's more likely that Bobrovsky is the catalyst that dooms the franchise to an eternity of underachieving mediocrity.

This Bobrovsky experiment is going to be a frustrating experience for Leafs Nation, and it's hard not to consider the soon-to-be retiree a winner under these circumstances. Bobrovsky is getting paid a king's ransom to torment Leafs fans and the media for the next three years.

Embrace your villain arc, Bobrovsky. Everybody but Leafs Nation is here for it.
Losers: Oilers' Netminders
We're convinced the Edmonton Oilers will be on a goaltender search in perpetuity. Devon Levi and Frederik Andersen were brought in on July 1, and we have no idea how Edmonton plans on managing its goaltending situation moving forward.

Formerly a top-ranked prospect, Levi has floundered in the NHL. With a career 3.29 goals-against average and .894 save percentage, he's not the answer between the pipes. More concerningly, Stan Bowman elected to bring in Andersen, thinking three below-average goalies would surely equate to a competent starter.

Believe it or not, the Oilers have a few goalie prospects knocking at the door. Instead of developing those prospects in the AHL, one of Levi, Andersen, or Tristan Jarry will be demoted to the Condors to steal the lion's share of the starter's minutes. With that, the Oilers are still left without a starting goalie. The few lifelines they have left in the minors will be left to languish and eventually depart for greener pastures.
Winners: Colorado Avalanche
For some reason, every NHL player is willing to take a discount to play for the Colorado Avalanche. That was the case again as free agency kicked off, with a few undervalued players bolstering the Avs' outlook.

Brett Kulak started the parade, re-upping with the Avalanche on a five-year $22.5 million pact. Brent Burns followed suit, coming back on a minimum deal for one more kick at the Stanley Cup can. Subsequently, Colorado lured Jaden Schwartz to town on just $9.75 million over three years, representing a $2 million pay cut relative to last year's salary. Then, they rounded out the opening day with a team-friendly $2.2 million, two-year deal for Noah Juulsen.

The Avalanche's moves may appear unspectacular, but these are exactly the type of players that will help them overcome the playoff hump. Now is the time to back the Avs as Stanley Cup Champs; the price only gets shorter from here.
Losers: Washington Capitals
If the Washington Capitals were trying to win a Stanley Cup five years ago, their 2026 free agent class would look like a steal. Unfortunately, they overpaid for aging talent in a young man's game, bringing the Alex Ovechkin era to an unceremonious close.

The Caps' prized offseason acquisition was a sign-and-trade for Alex Tuch. While he has 33 or more goals in three of the last four seasons, Tuch also has a dismal analytics profile. He has finished with an expected goals-for rating below 49.0% in two of the last three seasons, barely keeping his Corsi ratings above 50.0% over that stretch. Worse, Washington elected to pay Boone Jenner $23 million over the next four seasons. A rugged presence, Jenner doesn't possess the scoring prowess to command that kind of salary in today's NHL.

Both players are locked up until their late 30s, and neither is expected to live up to their salaries. The Capitals' demise started a few years ago. Based on their current trajectory, it will be a few more years before they climb back into the playoff picture.
Winner: Stuart Skinner
It's been a hell of a ride for Stuart Skinner. After backstopping the Oilers to consecutive Stanley Cup Finals, Skinner fell out of favor in Edmonton and was traded to the Penguins partway through the 2025-26 campaign. As he typically does, Skinner ebbed and flowed in Pittsburgh before hitting free agency on July 1. Thankfully, the Winnipeg Jets snatched him up, potentially kickstarting his redemption arc.

Connor Hellebuyck has requested a trade out of Winnipeg, potentially opening up the starter's job for the Jets. Considering their knack for developing netminders, this is the perfect solution to Skinner's woes.

One of two scenarios will play out this season. Either Skinner gets to apprentice under Hellebuyck in Winnipeg, or he benefits from the tutelage of the Jets' goalie coach. Either of those is an ideal outcome for an inconsistent netminder.

At his best, Stuart Skinner is a premier NHL goalie. Here's hoping the Jets can figure out how to maximize his talents.
Loser: Dallas Stars
For years, the Dallas Stars have been knocking at the door. They were runner-ups in the Western Conference Finals in three consecutive years, getting shown the door in the opening round of this year's postseason. Needing to attract some backend talent, the Stars were snubbed by a few noteworthy players.

Zach Werenski demanded a trade out of Columbus, stating his intention to suit up for any team other than the Blue Jackets. The Stars came knocking, and Werenski decided that rotting away on a non-competitive Jackets team was the better option. Moreover, Dallas has over $10 million in cap space to play with, and it couldn't land any of the available defensemen on the opening day of free agency.

Teams in the Central Division and Western Conference are getting better, and the Stars can't even convince a guy who demanded a trade to play with them. The Stars may improve via the trade market, but it looks increasingly unlikely.
Losers: Toronto Maple Leafs
Desperation is a wretched odor. When the rest of the NHL is looking around the room to see who is emitting that pungent smell, the Toronto Maple Leafs will shamefully head for the showers and apply an overwhelming dose of body spray.

To everyone's dismay, the Leafs brought in John Chayka as the General Manager earlier this offseason. Somehow, Chayka is even more disconnected from reality than we thought.

The Leafs made it a priority to target some fringe NHLers and overpay them. Colton Sissons fulfills a bottom-six role, contributing just 32 points and a -23 rating over the past couple of seasons. Previously a $2.8 million cap hit, Toronto saw it fit to pay him $4.2 million for the next two seasons. More confoundingly, Sergei Bobrovsky is set to earn a staggering $21 million over the next three seasons. This, despite the Russian netminder posting a 3.07 goals-against average, .877 save percentage, and -23.4 goals saved above average last season as a 37-year-old.

Of all the blunders the Leafs have made over the years, the 2026 opening day of free agency may go down as one of the worst.

Hopefully Kawhi Leonard pans out for Toronto; the Raptors are the only thing you have to look forward to.

Ranking the Biggest Losers and Winners From NHL Free Agency

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