- May 21, 2026
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John Chayka may not have been the most popular hire when he was named as the new general manager of the Toronto Maple Leafs, but he certainly hasn’t been shy about wheeling and dealing in the early days of his tenure.
After sending goaltender Joseph Woll and defenseman Simon Benoit to the Philadelphia Flyers for defenseman Emil Andrae, goaltender Samuel Ersson, and a third-round draft pick, Chayka made his biggest splash thus far on Friday by acquiring defenseman Darren Raddysh from the Tampa Bay Lightning for a fifth-round pick and signing him to a brand new eight-year, $68 million contract extension.
There’s been speculation that the Leafs could also be willing to move winger Matthew Knies for the right return, especially since it was reported that Toronto very nearly sent Knies to the Montreal Canadiens at this year’s trade deadline for a package of prospects and draft picks.
That deal, however, would’ve been made by the Leafs’ old regime. While speaking with the media on Friday following the acquisition of Raddysh, Chayka made it clear that a Knies trade isn’t likely anytime soon, calling it “not probable.”
While Chayka’s wording doesn’t completely rule out the possibility of a Knies trade, it would be surprising to see Toronto move off one of the few young, quality forwards in their organization.
Now that the Leafs have bolstered their blueline with the additions of Raddysh and Andrae, their offseason plan is taking shape. The Leafs will likely select Penn State winger Gavin McKenna with the first overall pick at June 26th’s NHL Entry Draft, which should give them an exciting mix of forwards that will include McKenna, Knies, second-year player Easton Cowan, and of course established stars Auston Matthews, William Nylander, and John Tavares.
Toronto seems to be banking on a revamped blueline, the addition of McKenna, and the direction of new head coach Jim Hiller to bring them back to the playoffs next season.
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After sending goaltender Joseph Woll and defenseman Simon Benoit to the Philadelphia Flyers for defenseman Emil Andrae, goaltender Samuel Ersson, and a third-round draft pick, Chayka made his biggest splash thus far on Friday by acquiring defenseman Darren Raddysh from the Tampa Bay Lightning for a fifth-round pick and signing him to a brand new eight-year, $68 million contract extension.
There’s been speculation that the Leafs could also be willing to move winger Matthew Knies for the right return, especially since it was reported that Toronto very nearly sent Knies to the Montreal Canadiens at this year’s trade deadline for a package of prospects and draft picks.
That deal, however, would’ve been made by the Leafs’ old regime. While speaking with the media on Friday following the acquisition of Raddysh, Chayka made it clear that a Knies trade isn’t likely anytime soon, calling it “not probable.”
While Chayka’s wording doesn’t completely rule out the possibility of a Knies trade, it would be surprising to see Toronto move off one of the few young, quality forwards in their organization.
Now that the Leafs have bolstered their blueline with the additions of Raddysh and Andrae, their offseason plan is taking shape. The Leafs will likely select Penn State winger Gavin McKenna with the first overall pick at June 26th’s NHL Entry Draft, which should give them an exciting mix of forwards that will include McKenna, Knies, second-year player Easton Cowan, and of course established stars Auston Matthews, William Nylander, and John Tavares.
Toronto seems to be banking on a revamped blueline, the addition of McKenna, and the direction of new head coach Jim Hiller to bring them back to the playoffs next season.
Continue reading...