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.

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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.

At a time when contending teams throw around second round draft picks like candy, the Oilers only managed to net themselves a fifth round pick in 2014 and a third round pick in 2015 from the Ottawa Senators.

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.

Reinhart has played 12 scoreless games for the Oilers and now finds himself in the minors. Sure, he could still develop into a top four defenseman, but the Oilers need help now and they’re not getting it. They may be regretting the decision to give the Islanders those two picks for Reinhart.

13 Paul Coffey dealt to Pittsburgh

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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.

Simpson was the only piece of value who came back to the Oilers in the deal as he posted three 30 goal seasons in Edmonton, including a career high 43 goals following the trade, while helping the Oilers to two more Cup victories, but it was far from a big enough return for the Hall of Fame defenseman in Coffey, who went on to win another Stanley Cup with the Penguins in 1991.

12 Oilers swap Lupul for Pitkanen

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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.

The pair of Pitkanen and Sanderson lasted just one season in Edmonton before Sanderson retired and Pitkanen was traded again. Lupul, meanwhile, posted back-to-back 20 goal seasons for the Flyers before once again being traded for Chris Pronger.

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.

In Carolina, Pitkanen’s offensive numbers rebounded and he became a top pairing defenseman for the Hurricanes before injuries derailed his career. As for Cole, he lasted less than one season in Edmonton, scoring just 16 goals and 27 points in 63 games, before being dealt back to Carolina.

10 Cole shipped back to Carolina

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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.

The Oilers received Patrick O’Sullivan and a second round pick in the deal, before flipping the pick to the Buffalo Sabres for Ales Kotalik. O’Sullivan was a huge disappointment in Edmonton. He posted just six points in 19 games to end the season and then finished the following season with 34 points in 73 games before being dealt to the Phoenix Coyotes and subsequently bought out. Kotalik, meanwhile, played just 19 games for the Oilers, recording eleven points, and then walked via free agency.

9 The Kurri trade

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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.

Mellanby played just two seasons with the Oilers before joining the Florida Panthers in the expansion draft, while Berube was traded to Toronto before the next season and Fisher never played a game for the Oilers.

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.

He held a heart-felt press conference to say goodbye to his long-time home and then went off to score 15 points in 18 games for the Islanders before adding four points in five postseason games. None of the players the Oilers received in return ever made any significant contributions and Alex Plante, who the Oilers used the first round pick on ended up being a draft bust.

7 The Pronger trade

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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.

This is a deal the Oilers had to make, but it also set the franchise back for years to come and paved the way for a string of future bad trades.

6 Oilers costly trade down the draft

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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.

The Oilers used their first pick on Sidney Crosby’s future junior linemate, Marc-Antoine Pouliot, and their second pick on Jean-Francois Jacques. The 74 combined career points from the pair, pale in comparison to the 410 points the Devils received from the player they selected 17th overall, Zach Parise.

5 Oilers don’t want Rangers to have Courtnall

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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.

Rather than match the offer sheet or decline and take the compensation, the Oilers chose to trade Courtnall to the Washington Capitals, who would match the offer sheet, in exchange for Greg Adams. Courtnall played two seasons in Washington, scoring a career high 42 goals and 80 points in 1988-89 and another 74 points the following year. As for Adams, he scored just nine points in 49 games for the Oilers before being dealt away at the 1989 trade deadline.

4 Sabres get Satan

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Miroslav Satan played parts of two NHL seasons with the Oilers before he was dealt at the 1997 trade deadline to the Buffalo Sabres for Craig Millar and Barrie Moore. The pair played a combined 40 games for the Oilers, while Satan went on to lead the Sabres in scoring six times in eight seasons, reaching the 30 goal mark three times – including a career high 40 goals in 1998-99 – and helped the Sabres to a 1999 Stanley Cup Final appearance.

3 Damphousse trade brings about worst Oilers era

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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.

Meanwhile, the Oilers went on to miss the playoffs for the first time in franchise history and posted their worst season to date in 1992-93. Corson was the biggest piece of the deal for the Oilers. He played three seasons in Edmonton, was named captain in 1994-95, later stripped of his captaincy after fighting with Jason Arnott over an assist, and joined the St. Louis Blues the following season.

2 Moose goes to the Big Apple

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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.

Messier would win the Hart Trophy and lead the Rangers to the league’s best record during his first season in New York. He would also help the Rangers end a 54-year Stanley Cup drought in 1994. Nicholls was the biggest piece coming back to Edmonton, but he played just 95 games for the Oilers, scoring 89 points, before he was dealt to the New Jersey Devils.

1 The Trade

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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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