Maple Leafs’ Cowan Chasing a First in Hockey History

The Toronto Maple Leafs prospect is already two-thirds of the way to a feat that may never have been accomplished before. If he completes it, there will be a parade. What stands between him and one of hockey’s rarest accomplishments?

Easton Cowan Shows the Relentless Drive of a Winner

When people talk about Easton Cowan, the conversation usually revolves around his scoring, relentless work ethic, or seemingly endless motor. Maybe they’re asking the wrong question. Instead of asking how many points Cowan might score in the NHL, perhaps we should be asking something much bigger. Could he be on the verge of completing one of hockey’s rarest championship journeys?

Cowan captured the Memorial Cup with the London Knights in 2025. One year later, he helped the Toronto Marlies win the Calder Cup, proving he could contribute to a championship team at the professional level before becoming a full-time NHL player.

Now comes the “what if?”

If the Toronto Maple Leafs were to win the Stanley Cup in 2027, Cowan would complete an extraordinary progression in three consecutive seasons: the Memorial Cup, the Calder Cup, and the Stanley Cup.

It’s possible that no player has ever completed that championship journey in three consecutive seasons. The challenge is proving it.

It’s Hard to Confirm Whether Any Other Hockey Player Has Won All Three in Consecutive Seasons

Hockey history stretches back more than a century across three different leagues. While players such as Mike Richards and Alex Killorn eventually won all three championships during their careers, confirming whether anyone has done it in consecutive seasons would require tracing championship rosters across generations of junior, AHL, and NHL teams.

Rather than make a claim that cannot be conclusively proven, it is enough to recognize that Cowan has the opportunity to accomplish something that is, at the very least, extraordinarily rare. Even if research someday uncovers another player who managed the feat, it would still place Cowan in exceptionally exclusive company.

More Than Three Trophies

More importantly, this potential accomplishment says something about the player Cowan is becoming. Each championship represents a different stage of a player’s development. The Memorial Cup teaches young players how to win at the junior level. The Calder Cup proves they can do it against seasoned professionals.

But the Stanley Cup is hockey’s ultimate prize.

Together, these championships represent a developmental journey that very few players ever complete. That is what makes Cowan’s path so intriguing. He isn’t simply collecting championships. He is collecting experiences. Every elimination game, every overtime period, and every pressure-packed shift teaches lessons that cannot be replicated in practice.

Championships also expose players to levels of expectation that simply do not exist during ordinary regular-season games. Every mistake matters a little more. Every shift carries greater weight. Learning how to handle those moments at a young age can shape a player’s confidence for years to come.

For years, one criticism of the Maple Leafs organization was that it developed talented players but not necessarily players who had experienced winning championships before arriving in the NHL. That narrative may be changing.

The Marlies’ Calder Cup championship gave several young Maple Leafs prospects something statistics cannot measure, a belief that they know what it takes to win when the games matter most. Confidence built through championships often becomes part of a team’s culture, with players carrying those expectations forward as they move up the organizational ladder.

Why This Isn’t as Crazy as It Sounds

At this point, some readers are probably asking why we’re even discussing the possibility of the Maple Leafs winning the Stanley Cup. It is a good question. Most oddsmakers currently give Toronto only about a two- or three-percent chance of winning it all. But hockey has a habit of ignoring the odds.

Very few people believed the Toronto Marlies were legitimate Calder Cup contenders last season. They had an inconsistent regular season, got hot at exactly the right time, received outstanding goaltending, and suddenly they were champions.

But the Maple Leafs also defied the odds by winning this year’s NHL Draft Lottery. Sports history is filled with teams that weren’t supposed to win, until they did. No one is predicting a Stanley Cup parade in Toronto next spring.

But improbable does not mean impossible. Without that small possibility, this conversation wouldn’t exist. Hockey is filled with unlikely stories that only seem inevitable after they happen. Every championship run begins as a possibility that many people dismiss before the season even starts.

The Journey Is the Story

Whether Cowan ultimately becomes the first player to complete this remarkable championship journey in three consecutive seasons may never be the most important part of the story. The real story is that he has already accomplished something few young players ever do.

Before playing a full NHL season, Easton Cowan has already learned how to win at both the junior and professional levels. Those experiences cannot guarantee NHL success, but they certainly provide a foundation that many prospects never have the opportunity to build.

If the next championship ever comes, it won’t simply complete an impressive résumé. It would complete one of hockey’s most extraordinary developmental journeys. It might also become the clearest sign yet that the Maple Leafs are developing not only talented players, but winners.

[Note: I want to thank long-time Maple Leafs fan Stan Smith for collaborating with me on this post. Stan’s Facebook profile can be found here.]