Maple Leafs Should Start Focusing on the Gavin McKenna Era

On Friday, June 19, it was announced that the Toronto Maple Leafs made one of the biggest splashes of the offseason. In a sign-and-trade with the Tampa Bay Lightning, they swapped a 2026 fifth-round pick for defenceman Darren Raddysh. The contract reportedly comes out to eight years at an annual cap hit of $8.5 million.

There will certainly be conversation about whether Raddysh’s impressive season in Tampa Bay can be replicated in a different environment. But that’s not the topic of discussion here. Rather, it’s about Toronto giving an eight-year deal to a 30-year-old player in general.

With the Maple Leafs just days away from presumably selecting Gavin McKenna at first overall in the 2026 NHL Draft, the future lies in the Penn State University winger’s hands. Yet Toronto’s management seems more focused on reviving what’s left of the Auston Matthews era—even if it’s at the expense of the 18-year-old phenom.

Maple Leafs Should Be More Committed to McKenna’s Prime

The Maple Leafs are about to have a No. 1 prospect—one who had the “generational” label for some time—in their system. While Toronto is admittedly in a unique situation, getting the top pick after unexpectedly missing the playoffs for the first time since 2016, there’s also a duty to put him in a position to thrive long-term.

It’s understandable why the Maple Leafs want to give their current core another chance. Some of the guys may be getting up there in age, as Matthews, William Nylander, John Tavares, and Raddysh will all be 29 or older when next season starts. But they’ll still be young enough to be core members of a championship team for a little while longer.

Plus, the salary cap is going up, which softens the blow of Raddysh’s cap hit. By the time he’s in Year 5, he’ll be making what is considered No. 4 defenceman money today.

However, you have to consider the end goal here: the Stanley Cup. This iteration of the Maple Leafs—even after they draft McKenna—is not objectively better than what came before it. Those teams, mind you, did not advance past the second round of the playoffs. Furthermore, as the core continues to age, its impact should only decline. Meaning, the best time to win is now, but almost nobody is picking Toronto to hoist Lord Stanley in 2027.

With that said, if the Maple Leafs want to add talent and maximize the current window, that’s fine. Winning the Cup in the next few seasons is still possible, and that’s not something you want to jeopardize. Blowing up the core to build around McKenna would be a drastic measure, even for an aging core that hasn’t gotten halfway to a championship yet. But that doesn’t justify an eight-year deal—one that will eat into several years of McKenna’s prime.

Long-term contracts, for 30-year-olds especially, are signed by teams knowing that they’ll probably age poorly. You’re getting a player at his best now and paying the consequences later. That’s how these things usually work.

But the only person paying that consequence will be McKenna. When he’s 26 years old, which should more or less be the heart of his prime, Toronto is set to still be paying a 38-year-old Raddysh.

Again, the Maple Leafs are well within their rights to run it back. Adding McKenna, Raddysh, Jim Hiller as head coach, and whatever else this summer could have the team re-enter the East’s contender bubble. They should start thinking about the burden that signing eight-year deals places on McKenna, though.

At face value, the Raddysh deal could be a solid one. Tampa Bay was a favourable environment, to be sure, but he played at a true top-pairing level, and his elite offensive upside from the blue line is something Toronto really hasn’t had in the Matthews era. But the McKenna era is only days away from starting—you have to think about his future, too.