The Edmonton Oilers currently have five picks in the 2021 NHL Entry Draft, but there’s a good chance that will change over the course of Friday and Saturday.
Related: 2021 NHL Draft Guide
In their history, the Oilers have made 29 Draft Day trades, involving 21 players and 66 picks. Ten of those deals have come in the last eight drafts, including last year when they traded a third-round pick to the San Jose Sharks in exchange for fourth and fifth-round selections, which Edmonton used to select Carter Savoie and Tylor Tullio, respectively.
It’s rolling the dice to make a trade, and the draft is always a crapshoot, so making a trade at the draft is the ultimate gamble. Here’s a look at five times it paid off for the Oilers, beginning with their very first NHL Draft after joining the league in 1979 via the World Hockey Association merger.
1979 Trade with Minnesota North Stars
Oilers acquire Dave Semenko and 3rd round pick (Mark Messier) in exchange for 2nd round pick (Neal Broten) and 3rd round pick (Kevin Maxwell)
Semenko had been a sizeable part of the Oilers during their final two seasons in the WHA. The problem was that the six-foot-three enforcer’s NHL rights were held by the Minnesota North Stars, so to keep Semenko in his lineup, Oilers coach Glen Sather had to swing a trade for the 22-year-old forward.
Edmonton received the 48th overall pick as part of the deal, which the Oilers then used to select Messier. An 18-year-old forward from St. Albert, AB, Messier was in his first year of NHL draft eligibility but had played pro the previous season with the Cincinnati Stingers and Indianapolis Racers in the WHA.
Messier spent 12 seasons with the Oilers, serving as captain for the last three (1988-89 to 1990-91), and was integral to all five of the team’s Stanley Cup titles (1984, 1985, 1987, 1988, 1990). He received the Conn Smythe Trophy in 1984 and was awarded the Hart Trophy as MVP of the 1989-90 season.
Among Edmonton’s all-time regular-season leaders, Messier ranks third in games (851), fourth in goals (392), second in assists (643), and third in points (1,043). Messier, who also won a sixth Stanley Cup in 1994 and second Hart Trophy in 1992 while playing for the New York Rangers, was inducted into the Hockey Hall of Fame in 2007.
Semenko, meanwhile, earned his keep as Wayne Gretzky’s unfailing bodyguard over parts of eight NHL seasons in Edmonton. Anyone who dared take a run at Edmonton’s superstar would have to answer to Semenko, who ranks sixth all-time on the Oilers with 981 penalty minutes.
After retiring, Semenko was a fixture around the Oilers organization, working in roles including radio analyst, assistant coach, scout and team ambassador. Sadly, Semenko passed away from pancreatic cancer at age 59 in 2017.
It must be said that the North Stars did alright for themselves with the deal, too. Broten, a native of Roseau, MN, became a Minnesota hockey icon and is regarded as the state’s greatest center. He played nearly 1,000 games with the franchise that drafted him and represented the North Stars at two All-Star Games. Broten was inducted into the United States Hockey Hall of Fame in 2000.
1999 Trade with Nashville Predators
Oilers acquire 3rd round pick (Mike Comrie) in exchange for Craig Millar
With the newly acquired 91st pick in 1999, the Oilers took Edmonton product Comrie, a center at the University of Michigan. He signed a three-year contract with the Oilers on Dec. 30, 2000, and made his debut that night on Hockey Night in Canada.
As a 20-year-old rookie, Comrie totaled 22 points in 41 regular-season games. In Game 4 of the first round of the 2001 playoffs against the Dallas Stars, he scored the overtime winner, an iconic goal in Oilers history.
Comrie led the Oilers in games (82), goals (33) and points (60) in 2001-02. The following season he notched 20 goals, including a team-leading six game-winners and 31 assists in 69 games. He became an RFA in the 2003 offseason.
Negotiations on a new contract with the Oilers fell apart and led to Comrie requesting a trade. An already contentious situation reached new levels of acrimony when a trade agreement was reached with the Anaheim Mighty Ducks, only to have Edmonton GM Kevin Lowe refuse to make the deal unless Comrie paid back half of the bonuses from his rookie contract.
Eventually, in December 2003, Comrie was dealt to the Philadelphia Flyers for Jeff Woywitka, a 2004 1st round pick (used to select Rob Schremp) and 2005 3rd round pick (used to select Danny Syvret), bringing a bitter end to what had started as such a feel-good story of the local kid made good.
Fortunately, this does have a happy ending: Comrie returned to the Oilers for the 2009-10 season, and his first game back in Edmonton ended with an unlikely standing ovation, perhaps the most memorable pre-season moment in Oilers history.
2000 Trade with New York Islanders
Oilers acquire Eric Brewer, Josh Green and 2nd round pick (Brad Winchester) in exchange for Roman Hamrlik
Of the many trades the Oilers made for financial reasons through the 90s and into the 00s, rarely did it turn out as positively as in the case of Hamrlik.
The Czech defenceman had been Edmonton’s representative in the 1999 All-Star Game and scored 45 points for the Oilers in 1999-00. In the 2000 offseason, he became a restricted free agent. He was set to go to arbitration, where he was expected to seek a contract worth at least $4 million per year, a significant upgrade from the $2.25 million he had been making. (from ‘No Holiday for Roman: Hamrlik Not Happy About Being Traded to the Isles’, The New York Post, 06/26/00). That was more than the cash-strapped Oilers could afford, forcing a move by Lowe, who was then just weeks into his role as Oilers GM.
Brewer excelled as a shutdown defenceman for the Oilers, so much so that he was named to the 2002 Canadian Olympic Team that won gold in Salt Lake City. The following year, he represented the Oilers at the NHL All-Star Game. In the 2005 offseason, Brewer was part of a package dealt to the St. Louis Blues for Chris Pronger, a pivotal trade that set Edmonton on the path to Game 7 of the 2006 Stanley Cup Final.
Winchester appeared in 78 regular-season games for the Oilers and suited up 10 times during that 2006 postseason run, scoring the winning goal in Game 2 of Edmonton’s first-round upset of the Detroit Red Wings. Fellow forward Green played in 88 regular-season and three playoff games as an Oiler.
Hamrlik signed a four-year contract worth $13 million with the Islanders before the 2000-01 season, becoming the Isles’ highest-paid player at the time. (from ‘Excitement as Hamrlik Signs,’ The New York Times, 09/08/00)
2002 Trade with Buffalo Sabres
Oilers acquire two second round picks (Jeff Deslauriers and Jarett Stoll) in exchange for Jochen Hecht
Lowe traded Hecht, a forward who had 40 points in his lone season with the Oilers in 2001-02, to get the 31st and 36th overall picks in 2002, which were used, respectively, to select goaltender Deslauriers and center Stoll.
Stoll played in five different seasons for the Oilers and was pivotal to their Stanley Cup Finalist team of 2005-06. That season, he played all 82 games and ranked third on the Oilers with 68 points (22 goals, 46 assists while leading the team with 243 shots. He then played all 24 playoffs games in the spring of 2006, notching 10 points (four goals, six assists).
Stoll was traded to the Los Angeles Kings on June 29, 2008, in a deal that brought blueliner Lubomir Visnovsky to Edmonton.
Deslauriers played 58 games total with the Oilers. In 2009-10, he led Oilers goalies with 16 wins and 3 shutouts in 48 games and was Edmonton’s Molson Cup winner for that season.
The swap also worked out well for the Sabres: Hecht played 10 seasons in Buffalo, scoring at least 15 goals on five occasions.
2015 Trade with New York Rangers
Oilers acquire Cam Talbot and 7th round pick (Ziyat Paigin) in exchange for 2nd round pick (Jonas Siegenthaler), 3rd round pick (Sergey Zborovskiy) and 7th round pick (Adam Huska)
In 2016-17, goaltender Talbot helped bring Edmonton out of the decade of darkness, winning a franchise-record 42 games as he backstopped Edmonton to its first postseason appearance in 10 seasons and a Western Conference First Round series victory over the Sharks.
Talbot won Edmonton’s Molson Cup award for 2015-16. On the franchise career leader lists for goalies, he ranks fifth in games (227) and wins (104) and sits third with 12 shutouts.
In 2019, Talbot was traded to the Flyers for Anthony Stolarz. He played last season for the Minnesota Wild. Of the four draft picks involved in the Oilers-Rangers deal, only Seigenthaler has reached the NHL.
What’s your pick for the Oilers’ best Draft Day trade? Let us know in the comments below!
Brian is an Edmonton-based sports writer and broadcaster. His experience includes working as a sports reporter for the Edmonton Sun, where he covered the Edmonton Oil Kings 2013-14 Memorial Cup championship season.