Edmonton Oilers

NHL Trade Talk Recap: Senators, Oilers & Maple Leafs’ Lesson

Senators move on from Tkachuk, Oilers lock in Dickinson, and Leafs’ Raddysh deal echoes a Hyman-style lesson.

by
Old Prof
June 21, 2026

In this edition (June 21, 2026) of NHL Trade Talk Recap, here is Sunday’s NHL news. A couple of teams moved on from tough situations and locked in the players they think fit the next chapter. The Senators pulled the trigger on a Brady Tkachuk trade to Florida once it was clear he wasn’t re-signing, and the room was already at peace with it. The Oilers did the responsible thing by extending Jason Dickinson for five more years to keep their third-line/PK/faceoff role stable. Finally, the Maple Leafs’ big swing on Darren Raddysh echoes the Zach Hyman lesson, just from the other side.

Senators Move On From Brady Tkachuk

The Brady Tkachuk trade to the Panthers on Sunday didn’t come out of nowhere. It sounds more like the Senators already knew the writing was on the wall. The organization reportedly learned he wasn’t going to re-sign, and once that became clear, Ottawa decided it was better for their long-term future to move him rather than let the situation linger and keep distracting everyone.

And here’s the part that really stands out. Multiple reports suggest the Senators’ players were basically fine with it. There was talk that the locker room wasn’t pushing for him to stay, and that the Brady noise had turned into a constant distraction for the team. Tkachuk had submitted a list of preferred destinations a few weeks back, with Florida among the options. Ottawa reportedly had conversations with other teams, too. In the end, the Senators got the trade done while the pressure was building. Now they can return to rebuild, potentially even shopping around for a big target like Jason Robertson.

It Was Time: Senators Players Were ‘Good’ With Brady Tkachuk Trade

Oilers Re-Up Jason Dickinson For 5 More Years

The Oilers signed Jason Dickinson to a new five-year contract extension after the two sides made “significant progress” on terms this weekend. This keeps him out of free agency, where he might’ve cashed in for a bit more. The Oilers get him at a slightly friendlier AAV than his last $4.25M cap hit.

The main question is the length. Dickinson’s not really a big offensive driver, so a longer deal can feel a little risky at age 30. But Edmonton values what he does. He’s a strong faceoff guy and a reliable penalty-killer, basically the kind of third-line center they’ve struggled to consistently find. It also lets Ryan Nugent-Hopkins stay in top-six territory and takes some pressure off guys like Josh Samanski to do too much too soon.

Even Bob Stauffer pointed out the “gamer” part of it, including the fact that Dickinson pushed through a serious LBI to play the final stretch of the Anaheim series. For the Oilers, this feels less like locking down a needed role guy and buying stability down the middle.

Oilers Sign Jason Dickinson to New 5-Year Extension

Raddysh’s 8-Year Deal and the Hyman Lesson

When Toronto gave Darren Raddysh an eight-year contract, a lot of people wondered, “Eight years for a 30-year-old?” That’s totally fair to worry about what happens in the back half. Would there be dead cap space, regression, and all that? But that’s not always how NHL teams think. They’re usually looking at the prime years first, not just fast-forwarding to Year 8.

What makes this feel extra interesting is how it mirrors the Zach Hyman story in reverse. Edmonton took a risk putting Hyman in a great spot beside Connor McDavid, and it turned him into a monster. Now, Toronto is doing the opposite of what they may haven’t done with Hyman before. The message from this Leafs leadership group is basically: swing for the upside in the next 4–5 years while you’ve got your Auston Matthews window, and don’t panic about how it might look at 37.

Maple Leafs Made a Decision They Wouldn’t Make Before