December is a pivotal month in the NHL. While the midpoint of the schedule hasn’t quite arrived, there have been more than enough games for teams to get a sense of their strengths and weaknesses, and potential for success moving forward. It’s early enough that if a team decides to shake things up, it can do so without punting on the season.
That’s why it’s not uncommon to see some major trades made at this time of year. The Edmonton Oilers have been involved in their share of December deals, including a blockbuster move just a couple weeks ago.
Related: Oilers Acquire Tristan Jarry & Spencer Stastney In Multiple Trades
On Dec. 12, Edmonton acquired goaltender Tristan Jarry and forward Samuel Poulin from the Pittsburgh Penguins in exchange for Stuart Skinner, defenceman Brett Kulak and a 2029 second-round draft selection. Here’s a look at where that trade ranks among December deals in Oilers history.
5) Trade With Rangers in 1992
On Dec. 11, 1992, following a lengthy contract holdout that dragged more than two months into the season, Oilers general manager Glen Sather dealt defenceman Kevin Lowe to the New York Rangers in exchange for forward Roman Oksiuta and a third-round pick in the 1993 NHL Draft (used to select Alexander Kerch). The trade marked the end of an era.
Lowe was the only remaining player that was part of all five of Edmonton’s Stanley Cup-winning teams (1984, 1985, 1987, 1988, 1990) and the last of the seven future Hall-of-Famers who formed the core of Edmonton’s 1980s hockey dynasty. He had served as Edmonton’s captain in the 1991-92 season.
Prior to trading Lowe, the Oilers had never failed to reach the playoffs. Following the defenceman’s departure, Edmonton would go on to miss the postseason each of the next four years. Meanwhile, Lowe won his sixth championship as a member of the Rangers in 1994.
Oksiuta and Karch played just 36 games and five games, respectively, as Oilers. Both were long gone by 1996-97, when Lowe returned to the Oilers as a free agent. Incidentally, that also was the season Edmonton finally returned to the postseason.
4) Trade with Penguins in 1983
On Dec. 5, 1983, the Oilers traded forward Tom Roulston, 26, to the Penguins for Kevin McClelland, a 21-year-old winger who had yet to play a full season in the NHL.
McClelland immediately became a fixture in the Oilers lineup, taking on an enforcer role. At a time when fighting was a significant part of the game, McClelland established himself as one of the NHL’s top scrappers.
The 190-pound forward spent nearly six years with the Oilers and was part of Edmonton’s first four Stanley Cup championship victories (1984, 1985, 1987, 1988). He finished first or second on the team in penalty minutes every season from 1983-84 to 1988-89.
McClelland was dealt to the Detroit Red Wings on Nov. 2, 1989. At the time of the trade, he was Edmonton’s all-time leader in penalty minutes for both the regular season (1,291) and playoffs (276). To this day, he has been surpassed by only Kelly Buchberger for regular season penalty minutes and Glenn Anderson for postseason penalty minutes.
3) Trade with Flyers in 2003
Arguably the nastiest contract dispute in Oilers history ended on Dec. 16, 2003, when Edmonton dealt centre Mike Comrie to the Philadelphia Flyers for highly touted defenseman prospect Jeff Woywitka, along with a Round 1 pick in the 2004 Draft (used to select forward Rob Schremp) and a Round 3 pick in the 2005 Draft (used to select defenceman Danny Syvret).
Comrie, a 23-year-old restricted free agent, had racked up 53 goals and 58 assists in 151 games over the prior two seasons combined. He was expected to be a big part of the team’s future before things turned ugly between him and Oilers general manager Kevin Lowe, who ironically had himself been involved in a holdout 11 Decembers earlier.
This is a trade that’s significant only because of what could have been. Woywitka never played for the Oilers; after two seasons in the American Hockey League (AHL), he was dealt to the St. Louis Blues in August 2005. Syvret and Schremp, meanwhile, only appeared in a handful of games each with the Oilers; Edmonton traded Syvret to Philadelphia in 2008 while Schremp left the Oilers via free agency in 2010.
Comrie never reached the level of his first few seasons in Edmonton. He wound up bouncing around the league for several years before ending up back with the Oilers in 2009-10.
2) Trade with Penguins in 2025
After reaching the Stanley Cup Final in consecutive postseasons only to be defeated by the Florida Panthers on both occasions, the Oilers decided that it was time for a change between the pipes.
Skinner accomplished some great things as an Oiler; he was an All-Star Game selection, a Calder Trophy finalist, and set the franchise record for consecutive wins as a goalie. But his lack of consistency was widely perceived as the factor holding Edmonton back from winning the championship. So when he got off to a subpar start this season, Oilers general manager Stan Bowman decided it was finally time to move on from the local product.
While Jarry doesn’t have the NHL playoff experience that Skinner possesses, the Oilers hope the 30-year-old can be the steady presence they’ve been missing in goal. Jarry won his first three starts with the Oilers, although he was hurt against the Boston Bruins on Dec. 18 and is currently sidelined for a couple weeks.
1) Trade with Lightning in 1997
On Dec. 30, 1997, the Oilers acquired top-pairing defenceman Roman Hamrlik and forward Paul Comrie in exchange for blueliner Bryan Marchment along with forwards Jason Bonsignore and Steve Kelley.
This was the first of two moves that Sather made in the span of a few days that transformed the Oilers’ season. The second came on Jan. 4, 1998, when Edmonton sent forward Jason Arnott and rearguard Bryan Muir to the New Jersey Devils in exchange for forwards Bill Guerin and Valeri Zelepukin.
After going 11-22-9 through its first 42 games and falling several points back of a playoff spot, Edmonton went 24-15-1 the rest of the way to clinch a postseason berth. The Oilers then upset the Colorado Avalanche in the opening round of the Stanley Cup Playoffs, before falling to the Dallas Stars in Round 2.
Hamrilk was a significant contributor to Edmonton’s amazing second half of the 1997-98 season, racking up six goals and 20 assists in 41 regular season games with the Oilers. The Czech blueliner went on to play two full seasons in Edmonton, totalling 32 points in 1998-99 when he was selected to the All-Star Game and 45 points in 1999-00. He was dealt to the New York Islanders in June 2000.
Twenty-eight years later, Edmonton’s incredible turnaround in 1997-98 remains almost impossible to top. But if Jarry can backstop the Oilers to a championship, the latest December trade by the Oilers will take over top spot on this list.
