Toronto Maple Leafs or Edmonton Oilers? Which Canadian Contender Is Truly Better Positioned Heading Into the 2025 NHL Offseason

The 2025 NHL offseason has arrived, and as the dust settles on another year of heartbreak for Canadian hockey fans, one question is dominating discussions across the country: Are the Toronto Maple Leafs or Edmonton Oilers better positioned to finally break the Canadian Stanley Cup drought? Both franchises enter this summer at a critical juncture, loaded with talent, facing major questions, and eyeing roster upgrades to make that elusive championship run a reality.

While both teams have superstars, passionate fanbases, and no shortage of pressure, their situations entering the offseason are vastly different. The Oilers, led by Connor McDavid and Leon Draisaitl, suffered another bitter playoff exit, fueling speculation about their long-term core and how much time remains to capitalize on their window. The Maple Leafs, meanwhile, are adjusting to a new-look front office under Brad Treliving, with the infamous “Core Four” still intact but their futures uncertain as contract deadlines loom.

Let’s break down where both teams stand and which Canadian juggernaut might truly be better positioned for success heading into one of the most pivotal offseasons in recent memory.

The Case for the Edmonton Oilers

For the Oilers, it begins and ends with McDavid and Draisaitl — two of the best players in the world, both still in their primes. Despite falling short yet again in the playoffs, the presence of this dynamic duo gives Edmonton an advantage few teams in the league can match. McDavid, coming off another historic season, continues to redefine offensive production, while Draisaitl remains one of the most complete power forwards in the game.

However, the clock is ticking. Draisaitl’s contract is set to expire after the 2025-26 season, and whispers are already swirling that this offseason could determine whether he commits long-term or tests free agency. The Oilers’ ability to construct a roster that convinces their German superstar to stay is crucial.

On the ice, the Oilers boast more than just star power. Zach Hyman delivered a career year, Ryan Nugent-Hopkins remains a valuable two-way contributor, and the blue line, led by Evan Bouchard and Darnell Nurse, provides offensive punch from the back end. Stuart Skinner has emerged as a capable starting goaltender, though questions persist about whether he can steal games when it matters most.

Financially, Edmonton faces limitations. With much of their salary cap tied up in big contracts, General Manager Ken Holland (or potentially his successor, should changes be made) will need to get creative to bolster depth, particularly on defense and in the bottom six forward group. The Oilers’ limited draft capital further complicates matters, making this offseason a balancing act of immediate needs versus long-term sustainability.

Yet, the Oilers can confidently claim they are in “win-now” mode with arguably the best player in the world at the height of his powers. If they can address their weaknesses — specifically defensive structure and depth scoring — Edmonton could be poised for another deep playoff run, assuming internal tensions don’t derail the process.

The Case for the Toronto Maple Leafs

Toronto’s situation is equally complex but offers a different type of intrigue. Under Brad Treliving, the Leafs are navigating a critical offseason, with decisions looming over cornerstone players like Mitch Marner and John Tavares. While Auston Matthews is locked in, and William Nylander has recommitted, the “Core Four” era may be approaching its final chapter.

The Leafs possess elite offensive firepower. Matthews remains one of the NHL’s premier snipers, and Nylander’s breakout campaign reinforced his status as an indispensable part of Toronto’s future. But after another first-round playoff disappointment, questions persist about whether this group has the right composition to succeed in the postseason grind.

Defensively, Toronto made strides, with Morgan Rielly anchoring the blue line and prospects like Timothy Liljegren showing promise. However, defensive consistency remains an issue, and the team’s inability to suppress elite playoff opponents has proven costly.

Goaltending is another wildcard. Joseph Woll displayed flashes of brilliance, but durability concerns and a small sample size raise valid doubts. The Leafs may need to explore veteran goaltending options to stabilize the crease and provide insurance behind their young netminder.

The Leafs enter the offseason with slightly more financial flexibility than the Oilers, particularly if they opt to move Marner or Tavares to free cap space. Such blockbuster trades could reshape the roster and inject fresh energy into a group that’s become synonymous with unmet expectations. Alternatively, Toronto may double down on the current core, banking on marginal improvements and internal growth to finally push them over the hump.

One advantage the Leafs hold is market appeal. As one of the league’s most lucrative franchises, Toronto remains an attractive destination for free agents seeking a big stage and the chance to be part of hockey’s most scrutinized market. Whether Treliving can leverage that appeal to land impactful depth pieces or a veteran goaltender remains to be seen.

Who’s Better Positioned?

Comparing the Oilers and Maple Leafs heading into this offseason boils down to a philosophical debate between certainty and flexibility.

Edmonton has the league’s most dominant superstar duo, a proven formula for regular season success, and a core that’s been battle-tested in deep playoff runs. But their window could close rapidly if they fail to convince Draisaitl to re-sign, making this offseason arguably their most consequential in decades.

Toronto, while lacking the same playoff pedigree, possesses more flexibility to reshape its roster and potentially change the narrative that has haunted this era of Maple Leafs hockey. With key contracts expiring soon, Treliving has the opportunity to chart a bold new course, provided ownership supports decisive moves that may rattle the fanbase but ultimately strengthen the team’s championship pursuit.

In terms of immediate readiness, Edmonton likely holds the edge. A roster built around McDavid and Draisaitl is automatically a contender, and subtle tweaks — especially on the blue line and in bottom-six scoring — could make them lethal. But the Oilers are under immense pressure to succeed now, with long-term uncertainty lurking just beneath the surface.

Toronto, on the other hand, straddles the line between contender and work-in-progress. Their elite offensive core remains intact for now, but foundational decisions this offseason will define whether they continue to tread water or finally assemble a roster capable of postseason breakthroughs.

Ultimately, both franchises face immense expectations, passionate — often impatient — fanbases, and the heavy burden of Canada’s decades-long Stanley Cup drought. But when evaluating who is better positioned right now, the answer leans slightly toward Edmonton, thanks to their superstar duo, recent playoff experience, and established roster core.

Still, that edge is razor-thin and heavily contingent on Draisaitl’s future, front office competence, and the ability to shore up weaknesses without compromising the team’s long-term prospects.

Toronto’s pathway is more uncertain but potentially more transformative. If bold moves are made, contracts are maneuvered wisely, and the supporting cast improves, the Leafs could leapfrog the Oilers as Canada’s top contender by the start of next season.

One thing is certain — for both franchises, this offseason isn’t just about adding pieces; it’s about seizing a window that may close faster than anyone expects. Canadian hockey’s two brightest hopes are at a crossroads, and their offseason choices will shape the NHL landscape for years to come.