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Flashback Friday: Looking at the Ryan Smyth trade 19 years ago that never should’ve happened

Photo credit: Lou Capozzola-USA TODAY Sports
Feb 27, 2026, 22:00 ESTUpdated: Feb 27, 2026, 22:17 EST
There have been two Edmonton Oilers to hit games played milestones this season.
For the first time in franchise history, a player played their 1,000th game with the Oilers, as Adam Henrique reached the quadruple-digit game mark on October 21st against the Ottawa Senators. On January 18th, Ryan Nugent-Hopkins became the first Oiler to play all of his 1,000 games with the Oilers.
Only one other player in franchise history, Kevin Lowe, would play 1,000 for the Oilers. Over his 19-season career, the defenceman played parts of 15 seasons with the Oilers, tallying 62 goals and 315 points in 1,037 games, reaching the 1,000 games played mark with the Oilers in the 1996-97 season, his final full season in the league. His 1,000th game was played with the New York Rangers in 1992-93.
Third on that list of most games played in the orange and blue is Ryan Smyth. Realistically, he should’ve been one of the rare players to play every single game with the same organization, but extension talks broke down after they couldn’t agree on the average annual value. The thing is, it wasn’t a huge difference either.
So on February 27th, 2007, the Oilers traded Smyth, a catalyst to the creation of Oilersnation. In this edition of Flashback Friday, we’ll look at the first big trade of the Decade of Darkness.
Trading Ryan Smyth
Let’s look at the context leading up to the trade, both in terms of Ryan Smyth’s career and the situation the Oilers were in. Drafted sixth overall in the 1994 draft, the Banff, Alberta native blossomed into a consistent 25+ goal scorer and 60+ point getter. In 2005-06, he scored a career-high 36 goals and added 30 assists, with his 66 points being the second-most in his career.
The Oilers had made the playoffs when Smyth was on their team in the past, usually playing either the Dallas Stars or Colorado Avalanche, but they never made it out of the second round, and hadn’t made it out of the first round since the 1997-98 season. That changed in the 2006 playoffs, as the eighth-seeded Oilers became the first team in National Hockey League history to make the Stanley Cup Finals, knocking off the Presidents’ Trophy-winning Detroit Red Wings, the San Jose Sharks, and the Colorado Avalanche.
Unfortunately, Dwayne Roloson suffered an injury late in Game 1 of the Stanley Cup Finals, and the Oilers ultimately lost 3-1 in Game 7 of the Finals to the Carolina Hurricanes. Along the way, Smyth scored seven goals and 16 points in 24 games. The best moment from that run was returning in the same game after losing a few teeth, then setting up a triple overtime winner to tie the series against the Sharks at two.
Smyth was on pace to set career-highs with the Oilers, scoring 31 goals and 53 points in 53 games, which is on pace for 45 goals and 82 points over an 82-game season. While Smyth was on pace to have a career-year, the Oilers were nine points out of a playoff spot with 19 games to go, and since they couldn’t agree to terms on an extension, they traded him.
On February 27th, 2007, the Oilers sent the heart and soul of the team to the New York Islanders in exchange for Robert Nilsson, Ryan O’Marra, and a 2007 first round pick that was used to select Alex Plante. Nilsson played 199 NHL games with the Oilers, scoring 31 goals and 98 points. O’Marra played 33 NHL games, scoring a goal and seven points, and Plante played 10 NHL games, picking up two assists.
Smyth finished his Oilers tenure with 265 goals and 549 points in 770 games, ranking seventh in all-time Oilers scoring at that point. He went on to score five goals and 15 points in the Islanders’ remaining 18 games, as the eighth-seeded Islanders fell to the Buffalo Sabres in the first round.
That off-season, Smyth signed a five-year deal with the Colorado Avalanche, playing 132 games with them where he scored 40 goals and 96 points. He was eventually traded to the Los Angeles Kings, where he scored 45 goals and 100 points in 149 games. But this story has a happy ending.
At the 2011 draft, the Oilers sent Colin Fraser and a seventh-round pick in 2012 to the Kings to bring Smyth home for the twilight of his career. He was still productive in 2011-12, the final year of that five-year deal, as he scored 19 goals and 46 points in 82 games. During the lockout shortened 2012-13 season, the Banff native scored two goals and 13 points, and in his final season, Smyth scored 10 goals and 23 points in 72 games.
One of the best moments from the Decade of Darkness came in Smyth’s final game. Donning the C above his heart, Captain Canada was a power play goal away from breaking the franchise record for power play goals in a career. Drawing eight minutes of penalties, the then 38-year-old played just under 24 minutes. While he wasn’t able to break the record, he had a nice send off to end his career in a moment that brings out tears.
In the end, Smyth played 971 regular season games with the Oilers, scoring 296 goals and 631 points. For his career, he played 1,270 games, with 386 goals and 842 points, but he should’ve remained an Oiler for the entirety of his career. It’s hard to look back on February 27th, 2007 with any fondness.
Ryley Delaney is a Nation Network writer for Oilersnation, FlamesNation, and Blue Jays Nation. Follow her on Twitter @Ryley__Delaney.
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