Winning championships is often the defining factor when separating good athletes from the greatest of all time. Tom Brady won seven Super Bowls, Michael Jordan six NBA championships, and Wayne Gretzky four Stanley Cups.

The Weight of Expectation

Connor McDavid, widely regarded as the best player in the world today, recently showcased his brilliance at Milano Cortina 2026, leading all competition with 13 points during the Olympics. However, despite his individual success, his team was defeated in the gold medal game, losing 2-1 to the USA.

This loss adds to a growing narrative surrounding McDavid’s performance in crucial moments.

McDavid Can’t Win the Big One?

Whereas some players struggle in big moments, McDavid’s playoff statistics suggest otherwise. He has 44 goals and 150 points in 96 career postseason games, averaging 1.56 points per game – the third-highest in NHL history, trailing only Mario Lemieux (1.60) and Wayne Gretzky (1.84).

Despite these impressive numbers, his performances in do-or-die games are under scrutiny.

In the past two Stanley Cup Finals, McDavid excelled, recording 42 points in 25 games during the first run and 33 points in 22 games in the most recent attempt. He even earned the Conn Smythe Trophy in a losing effort.

However, in both series, he failed to register a point in the deciding game. The Oilers lost Game 7 to the Florida Panthers after leading 3-0, and again lost to the Panthers in Game 6 the following year.

More recently, at the Olympics, McDavid was held pointless in the gold medal game against the United States.

He did secure a championship for Canada at the 4 Nations Face-Off with an overtime winner versus the US, but that tournament is not considered as significant as a Stanley Cup Final or Olympic event.

McDavid Deserves to Win

Even critics acknowledge that McDavid deserves success. As one observer noted, there have been plenty other players who have won while making far less contributions. The hope is that McDavid will achieve major team success, but until he does, the narrative surrounding his ability to win when it matters most will continue to grow.