Canadians live in interesting times. Canadian citizens who are fans of the playoff-bound Toronto Maple Leafs might argue that they live in even more complicated situations. Nowadays, it’s increasingly challenging to separate politics from sports, especially when a U.S. president casually suggests that Wayne Gretzky should be named the first governor of Canada after the United States annexes their neighbors to the north.
The genesis of this post is rooted in that surreal blend of commentary. It reflects on where we are now as Canadians and looks back to a rosier, more respectful chapter in the relationship between Canada and the United States. It’s a story where hockey, history, and shared values intersect.
The Maple Leafs Have Made the Postseason Again
As the Maple Leafs gear up for the playoffs, the political climate between Canada and the United States has become increasingly strained. President Donald Trump’s recent threats to annex Canada and the 25% tariffs on Canadian goods have sparked concern and a surge of national pride among Canadians. In contrast, during President Barack Obama’s tenure, Canada-U.S. relations were marked by mutual respect and cooperation, exemplified by initiatives like the Regulatory Cooperation Council aimed at harmonizing regulations to facilitate trade.
Obama’s History Fits the Maple Leafs Context: What Would He Advise the Maple Leafs?
As the Maple Leafs enter the postseason, fans might find more solace in Obama’s leadership style, emphasizing diplomacy and collaboration rather than the current confrontational approach. As the Maple Leafs strive for success on the ice, perhaps Obama’s example of thoughtful engagement offers the best guidance for navigating the situation’s complexities.
The regular season may be where teams build momentum, but the playoffs are where they build a legacy. For the Maple Leafs, a franchise rich in history and talent, the challenge isn’t about proving they can win. It’s about proving they can win when it matters most. That’s a lesson Obama — no stranger to pressure, poise in the face of problems, and leadership under the brightest lights — would understand.
Here are three pieces of advice Obama might offer the Maple Leafs as they head into another postseason with high expectations and higher stakes.
First, “Don’t Let the Past Write Your Future”
As President Obama said, “Progress isn’t always linear — but that doesn’t mean it’s not progress.”
If there’s one thing Obama would remind the Maple Leafs of, it’s that every season is a new chance to define who you are. Yes, the past looms large — early exits, missed chances, the weight of public expectation. But championships aren’t won by fearing ghosts. They’re won by staying present, focused, and believing that this year can be different — because you are different.
Obama’s rise — from a little-known Illinois state senator to President of the United States in just a few years — was built on this principle. Your past doesn’t limit your future unless you let it. The Maple Leafs have the skill, the structure, and the leadership. Now, they must enact the mindset.
Second, “Play Like a Team, Not a Collection of Talent”
As President Obama noted in his acceptance speech, “You don’t win elections (or playoff series) alone.”
Obama would be the first to point out that even the most gifted players must trust the system, buy into each other, and elevate those around them. In a playoff series, every shift matters. Every line combination, every defensive pairing, and every player must pull in the same direction. There should be no passengers or egos. No one should try to do it all.
He often credited his campaign teams—not just his speeches—with getting him to the White House. Like politics, hockey is won not just on big moments but in small, selfless ones: the backcheck, the blocked shot, smart line change, or putting oneself in the right place at the right time.
The Maple Leafs have elite players, but championships come when those players embrace the grind, the roles, and the “we” over the “me.”
Third, “Stay Calm. Stay Sharp. Stay Hungry.”
President Obama noted the importance of habits and routines. He would tell the Maple Leafs that, “in big moments, nerves are natural. But nerves don’t win games — habits do.”
The team has been here before — and the pressure can feel enormous. But Obama would tell the Maple Leafs what he told his staff before major debates or during national crises: control what you can control. Preparation. Poise. Belief. Action.
Stay focused on your game. Don’t chase the moment — own it. Whether it’s Auston Matthews needing to shake off a tight-checking game or Mitch Marner bouncing back from a tough shift, the advice holds: trust your training. Trust each other. Be unshakable in your intent, even if the breaks don’t go your way early.
Championship teams win not just because they’re talented, but because they keep their composure when others unravel. Keep skating, pushing, and working.
A Final Word from Obama: “This Time, Write a New Chapter”
Obama would likely end his advice with the measured encouragement he’s known for—the kind that sticks.
“You’ve been building toward this moment all season. You have the tools. You’ve got the talent. You’ve got the scars — and that’s not a weakness; that’s wisdom. Now it’s time to finish the work. Toronto is with you. The country is watching. And the story of this season is still yours to write.”
The Maple Leafs have everything they need. This time, the moment doesn’t have to be too big. This time, it can be theirs.
Related: Mitch Marner Shouldn’t Walk Away from Maple Leafs Greatness
