You can’t truly understand how to win until you’ve learned how to lose. It’s a lesson echoed across all arenas of life, but few know it as intimately or wear it as proudly as athletes. The Edmonton Oilers are a perfect example.
The team entered the NHL in 1979, one of four clubs absorbed from the defunct World Hockey Association. Young, talented, and full of potential, the Oilers quickly rose through the ranks. By 1983, they found themselves in the Stanley Cup Final, facing off against the dynastic New York Islanders. But the Islanders were still at the height of their powers and swept the Oilers with ease. For Edmonton, that defeat wasn’t just a loss—it was fuel.
The following season, the Oilers returned to the Final with a vengeance. This time, they dethroned the very team that had humbled them a year earlier. The victory in 1984 marked the end of the Islanders’ reign and the beginning of a dynasty in Edmonton.
Over the next few years, the Oilers became nearly unstoppable, capturing Stanley Cups in 1985, 1987, and 1988. With Wayne Gretzky leading the charge, they redefined offensive hockey and dazzled fans with their speed, skill, and swagger. Then, in 1988, the unthinkable happened—Gretzky was traded to the Los Angeles Kings. Many assumed the Oilers’ dominance would end there.
But the team had more to give. In 1990, they won their fifth Stanley Cup in seven years, defeating the Boston Bruins—this time without Gretzky. It was a powerful statement: the dynasty wasn’t built on one player alone.
That incredible run earned the Oilers recognition from The Hockey News as the greatest NHL dynasty of all time. Their core was a who’s who of hockey legends. Glenn Anderson, Grant Fuhr, Jari Kurri, Kevin Lowe, and Mark Messier—each of them key contributors to all five championships—would later be inducted into the Hockey Hall of Fame. Paul Coffey was a force on defense during the first three title runs, while Gretzky, enshrined in 1999, led the team through its early triumphs. And behind it all was Glen Sather, who coached the first four championship teams and served as general manager for all five. He was inducted into the Hall of Fame as a Builder in 1997.
The Oilers didn’t just win—they transformed the game. And they did it by turning a crushing loss into the foundation for greatness.
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