Easton Cowan has already checked off two of hockey’s biggest boxes, and the third one is the one that would make the whole sport take notice.
The Toronto Maple Leafs prospect won the Memorial Cup with the London Knights in 2025. A year later, he was part of the Toronto Marlies team that captured the Calder Cup. That puts him two-thirds of the way to a championship sequence that may never have happened before: Memorial Cup, Calder Cup, Stanley Cup, all in three straight seasons.
That last step is the one that turns this from a strong storyline into something bordering on hockey folklore. If the Maple Leafs win the Stanley Cup in 2027, Cowan would finish a run that would be almost impossible to ignore, even if history eventually turns up another player who managed it.
Hockey’s record books stretch across more than a century and three different levels of the game, which makes confirming a feat like this a real grind. Players such as Mike Richards and Alex Killorn have won all three trophies during their careers, but finding out whether anyone did it in consecutive seasons would mean digging through championship rosters from junior, the AHL and the NHL.
Still, the larger point is clear: Cowan is already in rare air.
And this isn’t just about stacking trophies. Each one marks a different stage of a player’s growth.
The Memorial Cup is about learning how to win as a junior. The Calder Cup shows a player can do it against pros who’ve been around the block.
The Stanley Cup is the final boss.
Cowan has already lived through two of those tests, and that matters. Championships aren’t just shiny hardware; they’re pressure laboratories.
Overtime shifts, elimination games, every mistake magnified - those are the moments that shape a player’s edge. You don’t fake that experience in practice.
That’s part of why this conversation has traction inside the Maple Leafs orbit. For years, one criticism of the organization was that it produced talented players who hadn’t yet been hardened by championship hockey before reaching the NHL. The Marlies’ Calder Cup run gave some of those young players something far more valuable than numbers on a stat sheet: proof that they know how to win when it counts.
Cowan’s reputation has long been built on scoring, work ethic and nonstop energy. The bigger picture is even more interesting. He’s not just piling up accomplishments; he’s moving through the stages of winning in a way very few players ever get the chance to do.
Of course, the final step is still a long shot. Oddsmakers currently give Toronto only about a two- or three-percent chance of winning the Stanley Cup.
But hockey has a way of making fools out of certainty. The Marlies weren’t widely viewed as real Calder Cup threats last season either.
They had an uneven regular season, caught fire at the right time, got strong goaltending and ended up champions. The Maple Leafs also beat the odds by winning this year’s NHL Draft Lottery.
So no, nobody is lining up a parade yet. But improbable and impossible are not the same thing.
That’s what makes Cowan’s path so compelling. Even before he’s played a full NHL season, he’s already learned how to win at both the junior and professional levels.
If the Stanley Cup ever gets added to that list, it would do more than complete a remarkable résumé. It would cap one of the strangest and most impressive development tracks hockey has ever seen.
In Other News...
Easton Cowan Suddenly Faces A Brutal Leafs Reality
The Maple Leafs spent the offseason piling up forward depth, and it has already made the picture around Easton Cowan a lot less straightforward. Toronto brought in Nick Paul, Colton Sissons, Brandon Duhaime and Teddy Blueger, then added Gavin McKenna in the draft, all while Jack Roslovic is projected to fit into a top-six role. For a young winger trying to force his way into the mix, that kind of added competition changes the math quickly.
Cowan still has a path, but it may hinge on what he does in training camp and how quickly he can show he belongs against a deeper group of NHL options. If the Leafs decide he needs more reps and more confidence before carving out a role, the AHL could be the most realistic next stop. For now, his challenge is less about talent than timing, with Torontos roster leaving very little room to learn on the job. [Read more 🡒]
Maple Leafs Suddenly Look Like A Team Fans Should Fear Again
After missing the playoffs, the Maple Leafs have had a full offseason to rest, reset and reshape the roster for 2026-27. The headlining addition is rookie Gavin McKenna, but Toronto also brought in a group that adds depth and experience in different spots, including Nick Paul, Colton Sissons, Jack Roslovic, Brandon Duhaime, defenseman Darren Raddysh and goaltender Sergei Bobrovsky.
It is the kind of broad roster makeover that can change the feel of a team quickly, especially for a club coming off a year that fell short of expectations. On paper, the mix gives Toronto more options up front, more stability on the back end and a new look in goal, which is enough to make the Leafs appear far more dangerous than they did a season ago, even if the real answer still has to wait for the games to start. [Read more 🡒]