Worst Oilers Trades Countdown – No. 2: Goodbye, Smytty

The Oilers were just one win away from being at the top of the hockey world in 2006, but it all came crashing down. And it didn’t stop.

The team went on an improbable, wild run through the playoffs that spring, taking down the Presidents’ Trophy-winning Red Wings and the Sharks and Mighty Ducks before eventually losing in Game 7 of the Stanley Cup Final to the Carolina Hurricanes. It was a heartbreaking end to an incredible story.

Unfortunately, there would be plenty more heartbreak on the horizon.

Shortly after the Stanley Cup had been awarded in Carolina, Chirs Pronger, the dominant defenceman who had played such a key role in the team’s playoff run, requested a trade out of town. The Oilers compiled and Pronger was dealt to the Ducks. Beyond Pronger, other veterans like Michael Peca, Jaroslav Spacek, Sergei Samsonov, and Georges Laraque left the team in free agency.

Still, despite the exodus, the Oilers had aspirations of being a playoff contender and proving to the world that their run to the Stanley Cup Final wasn’t some fluke. Breakout seasons from Ales Hemsky, Shawn Horcoff, Raffi Torres, and Jarrett Stoll created a reason for optimism that the Oilers would be able to overcome Pronger’s departure.

Also, Ryan Smyth, who had led the team with 36 goals in 2005-06, was still around. He had been a pillar of consistency for the past decade and, while many players came and went, imagining Smytty wearing any other uniform was unthinkable. There was one small issue of Smyth set to become a free agent at the end of the 2006-07 season, but surely the Oilers would be able to work out a deal for their heart and soul.

The Oilers got off to a strong start to the season but started to fade during the dog days of winter. Injuries to guys like Hemsky and underperformance from guys like Joffrey Lupul led to Edmonton’s supposedly deep offence to be less effective than expected.

By the time February rolled around, the Oilers were on the outside of a playoff spot looking in. A year earlier, general manager Kevin Lowe went all-in at the trade deadline, but, this year, it didn’t appear as though the team was worth investing in. He had already given up a first- and a second-round pick to acquire Dwayne Roloson and Sergei Samsonov the previous year, so buying again would be a big ask.

It was going to be a pretty boring deadline for the Oilers. Maybe Petr Sykora, who was on a one-year deal, would be shipped off to a contender. Maybe Brad Winchester, who wasn’t getting much playing time, would be flipped elsewhere for a new opportunity. The big news would surely be a Ryan Smyth contract extension, but that would come later on because Lowe wouldn’t want to overshadow Mark Messier’s jersey retirement ceremony with such an announcement.

And then Smyth got traded.

It came completely out of the blue. All reports out of the Oilers’ camp indicated that they were working to get a deal with Smyth done and that they were optimistic that it would happen. There were no rumours that sprung from opposing team scouts showing up to watch the team or that Lowe had been shopping Smyth around. It just happened.

Smyth got sent to the New York Islanders in exchange for prospects Robert Nilsson and Ryan O’Marra along with a first-round pick. Lowe wasn’t in attendance at Messier’s ceremony.

The response was that of pure shock. Just like that, the heart and soul of the team, the guy who had been the pillar of consistency for the past decade, the player who exemplified everything about what it meant to be an Oiler and an Edmontonian, was gone. The return? Who knows? Who cares? Ryan Smyth was now a member of the New York Islanders.

After that, the Oilers went into a tailspin. The night of the trade, following Messier’s jersey retirement ceremony, the team put out a completely lacklustre effort, losing 3-0 to the Phoenix Coyotes. That would be the second loss in what would eventually spiral into a 12-game losing streak.

The Oilers would win two games the rest of the way, a shootout victory over the Colorado Avalanche and their season-finale against the Calgary Flames. All told, without Smyth, they won just two of their final 19 games. They would finish the season with 71 points in the standings, their worst total since 1995-96, Smyth’s rookie season.

Over in New York, Smyth helped the Islanders claw into the eighth spot in the Eastern Conference, though they would quickly be dispatched in the first round of the playoffs by the Buffalo Sabres. He scored 15 points in 18 games as an Islander and led the team with four points in five games in the playoffs.

In return, Edmonton got a pack of magic beans. O’Marra was a bust and only ended up playing 33 games in the NHL. Nilsson had a good rookie season for the Oilers but disappeared after that. The first-round pick was used on Alex Plante, another bust who only played 10 games in the league.

I mean, in a vacuum, getting two former first-round picks and another future first-round pick in exchange for a rental isn’t really a bad return at all. If the organization’s player development and scouting had been better, maybe the return on this trade actually ends up looking really good and we end up viewing it as a necessary evil.

But that’s not really the issue with this trade. The issue was failing to commit to the heart and soul of the team.

It was reported later on that Smyth and Lowe were only $100,000 apart in negotiations. Smyth wanted $5,500,000 annually and Lowe would only go as high as $5,400,000 million. That’s absurd because, in the world of hockey contracts, $100,000 is a fairly negligible amount of money. It’s also absurd because Smyth was worth much more than that on the open market. In the off-season, he signed a deal with Colorado worth $6,250,000 annually over five years.

The team had had such a difficult time retaining key players over the years that this seemed like such a no-brainer. Since the 1980s dynasty, there had been a revolving door of star players who came and went — Vincent Damphousse, Jason Arnott, Bill Guerin, Doug Weight, Roman Hamrlik, Chris Pronger — either because they didn’t really want to be here or because the team couldn’t afford to keep them around.

And then, here was Smyth, the guy who was going to be an Oiler for life, and Lowe shipped him away over $100,000.

Fortunately, Smyth made an emotional return to Edmonton a few years later and he ended up finishing off his career as an Oiler. I think this whole situation becomes quite a bit easier to sweep under the rug knowing now that there’s a happy ending. Still, even after watching that ’06 team lose in Game 7, this was the first time I learned the extent to which sports could break your heart.