5 of the worst trades the Edmonton Oilers ever made

Despite being a historic franchise thanks to the dynasty they formed throughout the 1980s, the Edmonton Oilers went through some major downtimes before landing Connor McDavid.

Part of that was due to some poor drafting, but plenty of it had to do with some poor trades. Things have gotten better in that regard in recent years, but this team has had some very poor asset management which resulted in plenty of struggles. Let’s look at the five worst trades in Oilers franchise history.

Wayne Gretzky to the LA Kings (1988)

The Oilers choosing to trade Wayne Gretzky to the LA Kings during the 1988 offseason will likely always be the most shocking deal in NHL history. Despite coming off a 40-goal, 149-point season in just 64 games, the Oilers moved him, Mike Krushelnyski, and Marty McSorley in exchange for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million.

This trade never came even close to working out for the Oilers, who, despite winning a Cup in 1990, fell into a downward spiral shortly after. Gretzky, meanwhile, went on to score 246 goals and 918 points in 539 games with the Kings.

Mark Messier to the New York Rangers (1991)

Though the Mark Messier trade to the New York Rangers wasn’t as shocking, it was devastating nonetheless. Messier made it clear to the Oilers that he wanted a pay raise, and they weren’t willing to give him that, resulting in him being shipped out of town alongside Jeff Beukeboom for Bernie Nicholls, Louie DeBrusk, Steven Rice, and David Shaw.

Nicholls, who was the Oilers’ biggest get in this trade, played parts of just two seasons in Edmonton before being traded again. The Oilers have failed to win a Cup since this deal was made, whereas the Rangers, led by Messier, were able to win it all in 1994.

Ryan Smyth to the New York Islanders (2007)

As the 2007 deadline approached, it was clear that the Oilers would have to move on from Ryan Smyth. The two sides couldn’t find common ground in an extension, resulting in him being moved to the New York Islanders in exchange for Robert Nilsson, Ryan O’Marra, and a first-round pick.

Both Nilsson and O’Marra made little impact for the Oilers, while the first-round pick was used to select Alex Plante, who played in just 10 career NHL games. As for Smyth, he would go on to play very good hockey in stints with the Islanders, Colorado Avalanche, and Los Angeles Kings before returning to the Oilers as a free agent for the final three seasons of his career.

16th and 33rd overall picks to the New York Islanders (2015)

Just two months after being hired by the Oilers, Peter Chiarelli started his highly criticized tenure as their general manager by trading his first-round pick at No. 16 overall and his second at No. 33 in exchange for Griffin Reinhart. At the time, the Oilers needed to improve on the back end, and Chiarelli hoped this deal would help do just that.

Despite being taken fourth overall in the 2012 draft, Reinhart’s footspeed was not up to NHL level and resulted in him only playing 37 games in his career. As for the Islanders, they went on to select Mat Barzal at No. 16. Several other highly talented players were up for grabs when the selection was made, including Kyle Connor, Thomas Chabot, Joel Eriksson Ek, and Brock Boeser.

Taylor Hall to the New Jersey Devils (2016)

Though this trade didn’t go horribly for the Oilers, everyone was shocked seeing that they chose to trade Taylor Hall straight up for Adam Larsson. At the time, Hall was considered one of the most talented young forwards in the league, while Larsson was viewed as a top-four defenceman.

Larsson went on to play five seasons in Edmonton and was solid throughout. That said, Hall went on to win the Hart Trophy just one season after the deal was made, proving how lopsided it was in terms of value.

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