Winning a championship often comes after several hard lessons have been learned. Historically, a number of NHL franchises have faced adversity before winning the Stanley Cup. For a few teams, this included heartbreaking losses in the final.

This current version of the Edmonton Oilers has an opportunity to follow the example of these successful organizations. On an instinctive level, players have to take all those difficult emotions around losing and transform them into something positive and powerful.

After losing in two of the last three finals, we’ll find out if the Oilers have learned what it takes. I wouldn’t put too much weight on the early 2025-26 playoff exit. The team had injuries to key players, was exhausted from long playoff runs, and was constrained by their salary cap situation. In addition, their penalty kill wasn’t functioning all year, and their defensive play wasn’t strong enough.

Let’s look back at previous Stanley Cup champions who have learned to win after facing adversity. All of these teams ended up winning multiple championships.

The Oilers were swept in the 1983 Cup final by the powerhouse New York Islanders. Some of the team leaders and GM Glen Sather saw the Islanders in their dressing room after the final game. They saw the gruelling effects of the playoffs on the veteran New York team. Islander players were beat up; they’d sacrificed everything they had. There have been some attempts to rewrite history and say the Islanders were putting on a show. Well, let’s just say the scars and bruises weren’t fake. In addition, that version of the Oilers learned they had to play better defence and needed to add more depth. They began to play a 200-foot game and added more grit. After some hard lessons, Edmonton won five of the next seven Stanley Cups.

In the Yzerman era, the Detroit Red Wings had many playoff disappointments before winning back-to-back in 1997 and 1998. In 1994, the number-one-seed Red Wings were beaten by the number-eight-seed San Jose Sharks in seven games. The next year, the New Jersey Devils swept the Wings in the 1995 Stanley Cup final. Then in 1996, Detroit lost to the Colorado Avalanche in six games in the Western Conference final.

It took fourteen long years for the Red Wings to win the Cup; Yzerman was 32 years old. Some pundits have spoken about “The Yzerman moment“. Detroit’s captain scored the overtime winner in Game 7 of the Western Conference final on a spectacular play. It wasn’t the only reason the Wings finally broke through, but it symbolized their ascent. The Wings and their superstar captain began to play with more grit and played a better overall game.

It took four years for Sidney Crosby’s Pittsburgh Penguins to learn how to win. The Pens lost the 2008 final, but then went on to finally win in 2009, 2016, and 2017. See if this sounds familiar: Crosby’s team found a way to play better defence, be more resilient, and build a deeper lineup.

Some pundits have made the comparison between the 09′ Penguins and the current Oilers. McDavid and Crosby are both generational talents, and Draisaitl and Malkin (in his prime) are dominating power forwards. Pittsburgh also had talented Kris Letang leading their d-core, and the Oilers have Evan Bouchard. Will these similarly skilled teams have similar results when we look back in a few years?

Recently, the Oilers have seen up close what it takes to win. In the Stanley Cup final, Florida was crushed by the Vegas Golden Knights in 2023, and then went on to win in 2024 and 2025. The Panthers learned their lesson from their series against the Knights and prevailed in consecutive finals against the Oilers. The Florida championship teams were deeper and more experienced than the team that failed to go all the way.

Time will tell if Edmonton has learned from their recent defeats. They’re rested after two long playoff runs and have added important pieces. An experienced, no-nonsense coach has been brought in to lead them. Now we get to see if they have what it takes.

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