Top 15 Worst Trades in Edmonton Oilers History

If the Edmonton Oilers are ever going to turn the corner, then sooner or later they’re going to have to make some significant roster changes. Stockpiling high picks hasn’t worked as the team continues to flounder at the bottom of the NHL standings once again. In order to take the next step, it appears they’ll need to shake things up and move one or two of the young players they’ve drafted in order to acquire some help on the backend and possibly between the pipes.

There’s been much speculation that Ryan Nugent-Hopkins and Jordan Eberle are the most likely pieces to be moved out of Edmonton. Given the imminent return of Connor McDavid and the emergence of Leon Draisaitl in his absence, it would seem that the Oilers' depth down the middle makes Nugent-Hopkins expendable. As for the team’s wingers, Taylor Hall has become one of the top left wingers in all of the NHL and isn’t likely to be dealt anytime soon. Nail Yakupov may have been a target for trade speculation a few months ago, but seemed to have found chemistry alongside McDavid before the latter went down with an injury and then Yakupov suffered his own. The Oilers would likely want to see what they have in a healthy Yakupov before deciding what to do with him. Eberle, meanwhile, hasn’t produced as much as the Oilers would’ve liked so far this season and as a player whose been there for many of the lean years, it’s conceivable that Oilers may want to move on from him.

At this point, standing pat may be a riskier move for the Oilers than making a deal, but the Oilers have to make sure they get a potential deal right. After all, any blockbuster trade will help shape this Oilers roster for years to come and they should know better than anyone, that’s not a deal you want to mess up. Otherwise, it could go down in infamy with these 15 deals as the worst trades in Edmonton Oilers history.

15 Oilers don’t get enough for Hemsky

Perry Nelson-USA TODAY Sports

Ales Hemsky played parts of 11 seasons for the Oilers. He was there for the 2006 run to the Stanley Cup Final and many of the bleak years that followed. Hemsky always struggled to stay healthy, but always managed to produce when he was. When the Oilers began their rebuilding phase, they never maximized Hemsky’s trade value and instead waited until the 2014 trade deadline to finally move their long-time winger and his expiring contract.

14 Chiarelli moves the 16th and 33rd picks

Perry Nelson-USA TODAY Sports

One of Peter Chiarelli’s first moves as general manager was to trade the 16th and 33rd overall pick in the 2015 Draft to the New York Islanders for defensive prospect Griffin Reinhart, believing that Reinhart was capable of stepping into the Oilers lineup immediately as a potential top-four, puck-moving defenseman. That hasn’t happened.

13 Paul Coffey dealt to Pittsburgh


After the Oilers picked up their third Stanley Cup victory in 1987, a financial dispute with legendary defenseman Paul Coffey led to the him being traded to the Pittsburgh Penguins. Along with Coffey, the Penguins also received Dave Hunter and Wayne Van Dorp in exchange for Craig Simpson, Dave Hannan, Chris Joseph, and Moe Mantha.

12 Oilers swap Lupul for Pitkanen


Joffrey Lupul was supposed to be a key piece for the Oilers in the Chris Pronger trade, having scored 28 goals the season before the deal. However, Lupul’s lone season in Edmonton was a massive disappointment and he scored just 28 points in 81 games. Rather than hold on to the young winger and hope for a bounce back season, the Oilers instead shipped Lupul and captain Jason Smith to the Philadelphia Flyers for Joni Pitkanen, Geoff Sanderson, and a third round pick.

11 Oilers dump Pitkanen for Cole

Shaughn Butts/Edmonton

After the Oilers acquired Pitkanen from the Flyers in the Lupul deal, the young defenseman’s play failed to live up to expectations in Edmonton. His point total dropped from 43 points in 2006-07 with the Flyers to just 26 points in 63 games with the Oilers in 2007-08. Rather than hold on to him, the Oilers once again decided to cut bait with a player after just one season and shipped Pitkanen to the Carolina Hurricanes for Erik Cole.

10 Cole shipped back to Carolina


After dumping Lupul for Pitkanen and Pitkanen for Cole, this string of bad trades ended with the Oilers sending Cole back to Carolina at the 2009 trade deadline. In the three team deal, Cole returned to the Hurricanes, where he would post another 26 goal season, along with a fifth round pick from Edmonton and a second round pick from the Kings, while Justin Williams went to Los Angeles where he'd go on to help the Kings pick up two Stanley Cup victories.

9 The Kurri trade


After 10 seasons, 474 goals, 1,043 points and five Stanley Cup victories with the Oilers, Kurri chose not to re-sign in Edmonton following their 1990 Cup win and instead went to play in Italy for a year. The following offseason his rights were traded, along with Dave Brown and Corey Foster to the Philadelphia Flyers for Craig Fisher, Scott Mellanby and Craig Berube before the Flyers flipped Kurri to Los Angeles the same day. Kurri played parts of five seasons for the Kings and scored 87 points in 1992-93 and helped Gretzky and company to the 1993 Stanley Cup Final.

8 Ryan Smyth's teary-eyed goodbye

Chris Austin-USA TODAY Sports

Ryan Smyth was a hot commodity and a 12-year veteran of the Edmonton Oilers when the decision was made to move him at the 2007 trade deadline after the two sides couldn't come to an agreement on a contract extension. Smyth was dealt to the New York Islanders for Ryan O'Marra, Robert Nilsson, and a first round draft pick.

7 The Pronger trade


Following the Oilers run to the 2006 Stanley Cup Final, Chris Pronger requested a trade out of Edmonton. When the news became public it became foregone conclusion that any deal the Oilers made would be at a diminished return. In the end, he was dealt to the Anaheim Ducks for Joffrey Lupul, Ladislav Smid, a first round pick in 2007, second round pick in 2008, and a conditional pick in 2008 that became a first when the Ducks won the Stanley Cup the following spring.

The Oilers used that pick to draft Jordan Eberle, who remains the only significant piece in Edmonton from the deal. Lupul played just one disappointing season in Edmonton before being dealt away. Smid played parts of eight seasons for the Oilers, before he too was dealt away. The other draft picks paid no dividends for the Oilers.

6 Oilers costly trade down the draft


Some have long suggested that the Oilers should’ve used their position in the draft to trade down and add additional pieces. That’s not a strategy that has always worked for the Oilers. Holding the 17th overall pick at the 2003 NHL Draft, the Oilers opted to trade the pick to the New Jersey Devils for the 22nd and 68th overall picks.

5 Oilers don’t want Rangers to have Courtnall


The Oilers acquired Geoff Courtnall from the Boston Bruins in the midst of a 36 goal, 68 point season in 1987-88. Courtnall posted 8 points in 12 games for the Oilers and helped them to a 1988 Stanley Cup victory despite posting just three assists in 19 playoff games. The following summer, Courtnall became a restricted free agent and signed an offer sheet with the New York Rangers.

4 Sabres get Satan


3 Damphousse trade brings about worst Oilers era


Vincent Damphousse scored 38 goals and 89 points in his lone season in Edmonton in 1991-92, but the following summer he was dealt with a fourth round draft pick to the Montreal Canadiens for Shayne Corson, Brent Gilchrist, and Vladimir Vujtek. Damphousse went on to play parts of seven seasons in Montreal, reaching the 80 point mark four times, including a career high 97 points in 1992-93.

2 Moose goes to the Big Apple


Upset that the Oilers were letting Adam Graves walk as a free agent after the 1990-91 season, Mark Messier requested a trade out of Edmonton. He got his wish on October 4, 1991 when he was traded along with future considerations that would later become Jeff Beukeboom to the New York Rangers for Bernie Nicholls, Louie DeBrusk, Steven Rice and future considerations that would later become David Shaw.

1 The Trade


When it comes to bad Oilers trades, there can really only be one. After the Oilers picked up their fourth Stanley Cup victory in 1988, then owner Peter Pocklington, who was dealing with some financial troubles, consummated a deal with then Los Angeles Kings owner Bruce McNall for Wayne Gretzky. The deal sent “The Great One”, along with Mike Krushelnyski and Marty McSorley, to the Kings for Jimmy Carson, Martin Gelinas, three first round draft picks, and $15 million.

Carson would score 49 goals and 100 points in his lone full season in Edmonton and the Oilers would go on to win the Stanley Cup once more in 1990, but there’s no telling how many more they’ve could’ve won had they kept Gretzky. Instead he went on to play parts of eight seasons for the Kings, helping to grow the game in the United States and carrying the team to a Stanley Cup Final birth in 1993.

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Top 15 Worst Trades in Edmonton Oilers History