6 NHL Teams That Need to Make a Bold Trade in the 2026 Offseason

The second round of the Stanley Cup playoffs is ongoing, with the Carolina Hurricanes and Colorado Avalanche already advancing to the conference finals.

Meanwhile, the teams that failed to qualify for the postseason and those already eliminated are making plans to improve their rosters once the playoffs end in June.

With the salary cap rising from $95.5 million this season to $104 million for 2026-27, most clubs will be flush with additional cap dollars to invest in their roster. Given the shallow pool of talent in this summer's unrestricted free-agent market, those teams could attempt to add talent through trades.

Some teams could get audacious in the trade market for various reasons. Rebuilding clubs could pursue a player who can push them into playoff contention next season. Others could shake up their rosters by parting ways with one of their biggest stars.

Here's a look at six NHL clubs that must make a bold trade this summer.

Chicago Blackhawks

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Kyle Davidson has been Chicago's general manager since March 2022. During that time, he's been patiently rebuilding his roster with young talent, with Connor Bedard as the foundation player.

The 20-year-old center is a rising superstar who could one day lead them back to Stanley Cup glory.

So far, however, Davidson has yet to find a suitable scoring winger to skate alongside Bedard. Over the past two seasons, they've had veterans alongside their young star, such as Andre Burakovsky and Tyler Bertuzzi.

However, the Blackhawks need a young forward in his prime who can match Bedard's skills.

NHL insider Frank Seravalli believes Davidson must make a bold move to acquire an established young NHL scoring forward. He suggested targeting left winger Matthew Knies of the Toronto Maple Leafs or Jason Robertson of the Dallas Stars if the latter should become available in the trade market.

Knies or Robertson could be unavailable, but that shouldn't prevent Davidson from shopping around for other options. He has the cap room ($40.2 million) for 2026-27 and one of the best prospect pipelines in the league to draw on for trade bait to address that need.

Detroit Red Wings

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It's been 10 years since the Detroit Red Wings last appeared in the Stanley Cup playoffs. For the past seven seasons, they've been rebuilding under general manager Steve Yzerman. In each of the last three seasons, they tumbled out of playoff contention during the final weeks of the regular season.

A lack of skilled depth at center was among the reasons why they failed to qualify this season and for the last two years. There's little depth behind first-line center Dylan Larkin, whose only playoff appearance was as a Red Wings rookie in 2016.

Larkin is in the prime of his career, but Yzerman must find someone who can center the second line or take over the first line, allowing Larkin to drop down to the second line. With $32.7 million in cap space for 2026-27 and a deep prospect pool, the Wings GM has the dollars and tradeable assets to address this need.

On Apr. 13, MLive.com's Ansar Khan recommended the Red Wings get aggressive in this summer's trade market. He suggested the Red Wings pursue a center such as Robert Thomas of the St. Louis Blues, Elias Pettersson of the Vancouver Canucks, or Auston Matthews of the Toronto Maple Leafs if he becomes available.

San Jose Sharks

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Thanks to rising young stars such as Macklin Celebrini and Will Smith, the rebuilding San Jose Sharks exceeded expectations this season, jockeying for a Western Conference wild-card berth until the final week of the regular season.

Good fortune smiled on the Sharks during the 2026 NHL draft lottery, moving up from ninth overall to second overall in the draft order. That ensured they'll have a pick among the top four for the fourth straight year.

General manager Mike Grier could retain that pick and select another promising forward or defenseman with star potential. However, he could use it, along with his deep prospect pool and $41.5 million in salary-cap space, to put together a package that might fetch an established top-pairing blueliner.

Despite their rapid improvement, the Sharks lack a skillful puck-moving defenseman who can play big minutes. Grier could revisit his efforts to acquire Dougie Hamilton from the New Jersey Devils last summer. He could target Hamilton's young teammate, Simon Nemec, or pursue another good young blueliner.

Seattle Kraken

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Five years after their inaugural season, the Seattle Kraken have yet to reach the same level of success as the Vegas Golden Knights, who entered the league four years beforehand. While the Golden Knights won the Stanley Cup in 2023 and are a perennial playoff contender, the Kraken reached the playoffs only once.

The Kraken have spent the past five years as a defensive-minded club, hoping to use solid goaltending and blue-line depth to grind out wins. They've been lacking scoring punch for most of their tenure, and haven't had a scoring star to lead their offense and give the fans someone to get excited about.

That could push general manager Jason Botterill into the trade market in pursuit of a scoring forward. He attempted to acquire winger Artemi Panarin from the New York Rangers before the Olympic break. However, Panarin rejected his expensive contract offer and was instead traded to the Los Angeles Kings.

Having missed the playoffs for the third straight season, the Kraken could step up efforts to land a scorer via the trade market. They have the projected cap space ($28.4 million) to take on a high-salaried star. They also have two first-round picks in this year's draft and a deep prospect pool to draw on for trade bait.

Toronto Maple Leafs

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The Toronto Maple Leafs missed the playoffs for the first time in nine seasons, sparking changes in the front office and behind the bench. It also raised questions about Auston Matthews' future with the club. He has two seasons remaining on his contract and could force a trade if he's unhappy with their direction

Chris Johnston of The Athletic reported sources claimed Matthews wasn't sure if he would return to the Maple Leafs this fall. It's believed he wants to see significant roster improvement through trades and free agency, which will be difficult given their limited tradeable assets apart from their 2026 first-round pick.

Rather than delay the inevitable, Maple Leafs general manager John Chayka should find out which teams Matthews is willing to waive his no-movement clause for and trade him for the best possible return. It will upset Leafs fans in the short term, but it could help them quickly rebuild over the next three or four years.

The Leafs have some decent players to build around, including wingers William Nylander and Matthew Knies, who are under long-term contracts. Meanwhile, they can use the first-overall pick in this year's draft to select a promising youngster who could become a future franchise player.

Winnipeg Jets

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A year ago, the Winnipeg Jets enjoyed the best regular season in franchise history by winning the Presidents' Trophy. A year later, they missed the playoffs, raising concerns from superstar goaltender Connor Hellebuyck about the club's direction and worrying one Winnipeg pundit about his future with the Jets.

Hellebuyck is under contract through 2030-31 and won't be traded unless he asks for it. There's no indication that he wants out of Winnipeg, but his remarks should motivate general manager Kevin Cheveldayoff to improve the roster and get them back on the right track.

On Apr. 21, Murat Ates of The Athletic suggested the Jets attempt to find a reliable second-line center. He proposed pursuing an affordable player stuck in a third-line role with another team, such as Mavrik Bourque of the Dallas Stars or Peyton Krebs of the Buffalo Sabres.

A bolder move to address that need could be peddling their first-round pick in this year's draft, which is eighth overall. Sportsnet's Ryan Dixon suggested that move, given their Stanley Cup aspirations. It could fetch them a more established second-liner who could take some of the burden off first-line center Mark Scheifele.

Standings via NHL.com. Contract and salary cap info via PuckPedia. Prospect info via The Athletic.