The Oilers already had high-drafted wingers such as Taylor Hall and Jordan Eberle in their organization, yet still went with the talented Russian forward with the No. 1 pick of the 2012 NHL draft.
The selection hasn’t worked out for either side and Yakupov reportedly asked for a trade out of Edmonton prior to this year’s deadline.
Luckily for Yakupov’s camp, it’s hardly unprecedented to trade a No. 1 overall pick.
So we decided to get our Johnnie Cochran on (yes, I've been watching too much of the O.J. Simpson show on FX) and look at some past precedent.
Looking back at the last 30 years or so, here's how teams have fared after trading their No. 1 picks and whether or not the deals worked out -- either in the short or long term.
Name: Erik Johnson
Drafted by: St. Louis Blues in 2006
Trade (2011): Johnson, Jay McClement, and a 2011 first-round pick to the Colorado Avalanche for Kevin Shattenkirk, Chris Stewart, a 2011 second-round pick.
The result: Johnson has turned into a solid, but unspectacular player for the Avalanche. He's averaged 22:46 of ice time per game in six seasons with Colorado, but it's safe to say the Blues got the better end of this deal as Shattenkirk has provided an upgrade both offensively and defensively on the blue line.
Name: Rick Nash
Drafted by: Columbus Blue Jackets in 2002
Trade (2012): Nash, Steven Delisle and a 2013 third-round pick to New York Rangers for Brandon Dubinsky, Artem Anisimov, Tim Erixon and a 2013 first-round pick.
The result: Nash, the most productive offensive player in Blue Jackets history, asked out of Columbus after just one playoff appearance in nine seasons. The Blue Jackets got a heart-and-soul player (Dubinsky) in return and used Anisimov in their trade to bring in Brandon Saad. But the team hasn't been very productive since the deal. Meanwhile, Nash is still capable of big offensive numbers but is having a down season in 2015-16.
Name: Ilya Kovalchuk
Drafted by: Atlanta Thrashers in 2001
Trade (2010): Kovalchuk, Anssi Salmela, a 2010 second-round pick to the New Jersey Devils for Johnny Oduya, Niclas Bergfors, Patrice Cormier, a 2010 first-round pick, and a 2010 second-round pick.
The result: The Thrashers struck out big in this trade, not landing a player of substance outside of Oduya in exchange for the dynamic talent. The deal provided short-term benefits for New Jersey as Kovalchuk helped the Devils reach the Stanley Cup final in 2012. The Russian sniper left New Jersey on ugly terms, retiring from the Devils to join the KHL after signing a contract that was initially ruled as circumventing the salary cap.
Name: Patrik Stefan
Drafted by: Atlanta Thrashers in 1999
Trade (2006): Stefan and Jaroslav Modry to the Dallas Stars for Niko Kapanen, and a 2006 seventh-round pick.
The result: Stefan was a big-time draft bust with Atlanta, never exceeding 14 goals in a season, and only lasted 41 games with the Stars following the trade. He's best known in Dallas for a blooper that included him missing a wide open net.
Name: Joe Thornton
Drafted by: Boston Bruins in 1997
Trade (2005): Thornton to San Jose for Brad Stuart, Marco Sturm, and Wayne Primeau.
The result: The Bruins got completely waxed. Thornton has been an all-star calibre player over 11 seasons with the Sharks, scoring 879 points in 830 games. It took the Bruins a year or two to recover from the deal, but they eventually won the Stanley Cup in 2010-11.
Name: Bryan Berard
Drafted by: Ottawa Senators in 1995
Trade (1996): Berard, Don Beaupre, Martin Straka to New York Islanders for Wade Redden and Damian Rhodes.
The result: Berard refused to report after he was drafted by Ottawa but the Senators got a great return as Redden become a staple on their blue line for over a decade. The 1995 No. 1 pick was initially successful with the Islanders, winning the Calder Trophy in 1996-97, but was traded to the Toronto Maple Leafs after just four seasons in Long Island.
Name: Ed Jovanovski
Drafted by: Florida Panthers in 1994
Trade (1999): Jovanovski, Dave Gagner, Mike Brown, Kevin Weeks, and a 2000 first-round pick to the Vancouver Canucks for Pavel Bure, Bret Hedican, Brad Ference, and a 2000 third-round pick.
The result: Jovanovski only played in Florida for parts of four seasons, but helped the Panthers reach the Cup final in 1995-96. Jovanovski was viewed locally as a disappointment by the time he was dealt to Vancouver. He regained his form quickly and became a building block with Vancouver while Bure, the key on Florida's end, had two 50-plus goal seasons with the Panthers in four years.
Name: Alexandre Daigle
Drafted by: Ottawa Senators in 1993
Trade (1998): Daigle traded to the Flyers for Vaclav Prospal, Pat Falloon, and a 1998 second-round pick.
The result: Ottawa selected Daigle over future superstars such as Paul Kariya and Chris Pronger. He had a strong rookie season in Ottawa but the team grew tired of his lack of production after four years and shipped the Laval, Que., native to Philadelphia. Daigle only lasted two seasons with the the Flyers and after brief stints with the Lightning and Rangers, he was out of hockey by the age of 25. He briefly returned with Pittsburgh and Minnesota from 2002-06 and had one 20-goal season with the Wild.
Name: Roman Hamrlik
Drafted by: Tampa Bay Lightning in 1992
Trade (1997): Hamrlik, Paul Comrie traded to the Edmonton Oilers for Bryan Marchment, Steve Kelly and Jason Bonsignore.
The result: Hamrlik lasted 20 seasons in the NHL and played over 1,300 games but he never made a huge impact in Edmonton following his trade from Tampa Bay. He played only 196 games in three seasons for the Oilers, but the team qualified for the post-season in every season he was with the club. Hard to imagine, isn't it?
Name: Eric Lindros
Drafted by: Quebec Nordiques in 1991
Trade (1992): Traded to the Philadelphia Flyers for Peter Forsberg, Steve Duchesne, Kerry Huffman, Mike Ricci, Ron Hextall, a first-round pick, $15 million, and future considerations.
The result: The Lindros break-up with Quebec is one of the biggest stories in NHL history. Prior to the draft, he made it abundantly clear he wouldn't sign with the Nordiques if they picked him so eventually Quebec worked out two trades -- with Philadelphia and the Rangers -- before an arbitrator ruled in favour of the Flyers. The deal ended up working out for both sides as Lindros helped the Flyers reach the Cup final with Phiadelphia and won a Hart Trophy while Quebec, which saw most of the benefits when they later relocated to Colorado, got incredible production from Forsberg. Ricci helped the Avalanche win a Stanley Cup in 1995-96.
Name: Owen Nolan
Drafted by: Quebec Nordiques in 1990
Trade (1995): Nolan to the San Jose Sharks for Sandis Ozolinsh
The result: Nolan was a productive player for the Nordiques, exceeding the 30-goal mark in each of his three seasons with Quebec, but was dealt away after just nine games in the 1995-96 season when they moved to Colorado. Ozolinsh became a dynamic player (especially on the power play) for Colorado immediately, winning the Cup in 1996 and finishing third in the Norris Trophy in 1996-97. Nolan became one of the league's best power forwards with the Sharks, scoring 206 goals with 245 assists in 568 games.
Name: Mats Sundin
Drafted by: Quebec Nordiques in 1989
Trade (1994): Sundin, Garth Butcher, Todd Warriner, and a 1994 first-round pick to the Toronto Maple Leafs for Wendel Clark, Sylvain Lefebvre, Landon Wilson, and a 1994 first-round pick.
The result: This was the only trade on this list that included two No. 1 overall picks. Toronto at the time, as Damien Cox wrote looking back at the deal last July, were interested in upgrading at centre. Quebec had Joe Sakic, Peter Forsberg, Sundin, and Mike Ricci and initially targeted Ricci. Once Sundin's name got included, it required the team to move Clark, the team's fan favourite and local hero. While it was a difficult decision for then-GM Cliff Fletcher, it was a huge steal for the Maple Leafs.
Sundin became one of the most productive offensive players in franchise history and led the team to several deep playoff appearances while Clark returned to the Maple Leafs on two other occasions. The hard-nosed winger only played 37 games with the Nordiques before he was traded to the Islanders.