The Two Trades That Broke Oilers Fans’ Hearts: Wayne Gretzky and Ryan Smyth

The Edmonton Oilers have made plenty of trades throughout their history, but two stand above almost all the others when it comes to breaking the hearts of their fans. Nearly two decades apart, the Oilers traded away Wayne Gretzky and Ryan Smyth — two players who represented very different eras of the franchise. Gretzky was the greatest player in hockey and the face of an NHL dynasty. Smyth was the hometown-feeling warrior who became the heart and soul of the Oilers. Both trades shocked Edmonton, and both remain unforgettable pieces of Oilers history.

The Wayne Gretzky trade on August 9, 1988, is still one of the most famous trades in sports history. Just months after Gretzky helped Edmonton win its fourth Stanley Cup in five years, the Oilers sent him, Marty McSorley and Mike Krushelnyski to the Los Angeles Kings. Edmonton received Jimmy Carson, Martin Gelinas, three first-round picks and $15 million in cash.

At the time, it was almost impossible for Oilers fans to understand. Gretzky wasn’t simply another superstar. He was the face of the franchise, the best player in the world and the centerpiece of one of the greatest teams hockey had ever seen. He had already won eight Hart Trophies in nine seasons with Edmonton and had led the Oilers to four Stanley Cups. The idea of trading him seemed almost unthinkable.

The trade did change hockey forever, though. Gretzky helped put hockey on the map in Los Angeles, eventually taking the Kings to the 1993 Stanley Cup Final. Edmonton, meanwhile, managed to win one more Stanley Cup in 1990 without him. The Oilers also received significant future assets from the deal, including draft picks and young players. Looking back, the trade was far more complicated than simply saying Edmonton “lost” it.

Then came February 27, 2007. This time, Edmonton traded away someone who felt completely different from Gretzky but was just as important emotionally. Ryan Smyth was dealt to the New York Islanders at the trade deadline after contract negotiations with the Oilers broke down. Edmonton received Robert Nilsson, Ryan O’Marra and a first-round pick in the 2007 NHL Draft.

Smyth’s departure hurt in a different way. He had spent 770 games with Edmonton and had become the kind of player fans identified with the city itself. He was tough, emotional, willing to go into the dirty areas and seemingly impossible to separate from the Oilers identity. When the trade happened, Smyth was visibly emotional while saying goodbye to Edmonton, telling reporters that the city had been home to him and his family for 12 years.

The timing made the Smyth trade even more painful. The Oilers had just reached the Stanley Cup Final the previous season, and Smyth had been a huge part of that run. Edmonton was still trying to remain competitive when the contract talks fell apart. Rather than risk losing Smyth for nothing in free agency, general manager Kevin Lowe made the difficult decision to trade him.

There is also an interesting connection between the two trades. On the day Smyth was traded, he reportedly pointed out that even legends like Gretzky and Mark Messier had been traded by the Oilers. That was the reality of Edmonton hockey: no matter how important a player became, the business side of the NHL could eventually win.

The Gretzky trade changed the NHL. The Smyth trade changed how an entire generation of Oilers fans viewed their team. One was a shocking blockbuster involving the greatest player in hockey history. The other was a painful deadline decision involving a player many fans believed should have been an Oiler for life.

And that’s probably why both trades still get talked about today. Edmonton fans have seen some incredible players come through the organization, but Gretzky and Smyth represented something more. One was the superstar who made the Oilers a dynasty. The other was the player who embodied what it meant to be an Edmonton Oiler. Losing either one hurt. Losing both became part of the franchise’s history.