The Edmonton Oilers had an absolutely miserable 10-year stretch of drafting from the mid-80s to the early 90s.

They got off to an amazing start, selecting Kevin Lowe, Mark Messier, and Glenn Anderson with their first-ever three picks in 1979. They continued hitting home runs the following couple of years, drafting Paul Coffey, Jari Kurri, Andy Moog, Grant Fuhr, and Steve Smith in 1980 and 1981.

But after that? The Oilers had a hell of a time at the draft. They had a few nice finds like Esa Tikkanen, Jeff Beukeboom, and Kelly Buchberger here and there, but the team’s stretch of drafting over this 10-year span featured way more whiffs than hits. Using top picks on Jason Soules? Scott Allison? Joe Hulbig? Yikes!

This trend of miserable drafting came to an end in 1993 when the Oilers stepped up to the podium and selected Jason Arnott from the Oshawa Generals. A big, strong, talented centre, Arnott was the best player the Oilers had drafted in a decade. He broke into the league in 1993-94 and immediately scored 33 goals and 68 points. That showing was good enough for Arnott to be voted runner-up for the Calder Trophy, second only to some guy named Martin Brodeur.

Arnott became Edmonton’s beacon of hope in a difficult time. He was their consolation prize for missing the playoff for the first time ever and he was going to be the guy to help get the team back to their glory days. Not only would Arnott help the Oilers get back into the playoffs a few years later, his ensuing trade tree would help the Oilers make their Stanley Cup Final run in 2006 and also help the team end their decade-long drought in 2017.

Arnott spent parts of five seasons with the Oilers, scoring 100 goals and 239 points over 286 games. As great as he was right off the hop, Arnott’s game seemed to slow down over time.

In January of 1998, the Oilers sent Arnott along with defenceman Bryan Muir to the New Jersey Devils in exchange for Bill Guerin and Valeri Zelepukin. The deal was centred around two struggling forwards, Guerin and Arnott, who both needed a change of scenery. Arnott has just five goals in 35 games on the season for the Oilers at that point while Guerin had held out until late November due to a contract dispute with general manager Lou Lamoriello.

This trade was part of a mid-season shake-up for the Oilers. Just a few days earlier, the Oilers had dealt two former top draft picks, Jason Bonsignore and Steve Kelly, to the Tampa Bay Lightning in exchange for Roman Hamrlik and Paul Comrie. Within a span of under a week, the Oilers’ top picks from the 1993, 1994, and 1995 drafts were gone.

At the time of the trade, the Oilers were mired in a five-game losing skid that brought them to 11-22-9 on the season. This deal seemed to light the team on fire, as they immediately went on a six-game winning streak. Edmonton would have a solid second half of the season and a four-game winning streak to finish things off at the end helped propel them into a playoff spot where they would shock the Colorado Avalanche in the first round.

Guerin would play two-and-a-half more seasons for the Oilers, tallying 79 goals and 161 points over the course of 211 games. He also played the role of tough guy for the Oilers up front, racking up 354 penalty minutes over his time in Edmonton.

A little over a month into the 2000-01 season, Guerin was shipped to Boston along with Edmonton’s 2001 first-round pick for Anson Carter and Boston’s 2001 first- and second-round picks. Also, elsewhere in this trade tree, Zelepukin was sent to Philadelphia for Daniel Lacroix, who only played a few games in Edmonton. This deal had a lot of ramifications for the eventual 2006 Stanley Cup Final run team.

A key part of this trade was behind the scenes. Remember “you can view it as Hall for Larsson, Lucic, and Puljujarvi” from a few years back? That’s nothing new. Read the first line of Mark Spector’s article above.

General manager Kevin Lowe freed up some cash that the Oilers would use to ink Mike Comrie to an incentive-laden entry-level deal. Comrie was a fourth-round draft pick of the Oilers in 1999, but, thanks to a loophole in the Collective Bargaining Agreement (as he left college to play in the CHL as an over-ager), he became a free agent, free to sign an entry-level deal anywhere.

Comrie would become a local hero in Edmonton, tallying 74 goals and 154 points in 235 games over three seasons. But that status changed quickly as Comrie held out at the end of his entry-level deal and was eventually traded to the Flyers for Danny Syvret, Jeff Woywitka, and a first-round pick that was used on Rob Schremp.

Circling back, the Oilers got Anson Carter, a late-bloomer, power-forward winger in exchange for Guerin along with a couple of draft picks. They used the first-rounder on Ales Hemsky and the second-rounder on Doug Lynch. 

Carter wasn’t with the Oilers for long, but he became a fan favourite for his offensive prowess and gritty style of play. Over 211 games with the Oilers, Carter scored 69 goals and 157 points. At the 2003 trade deadline, Carter was traded along with Ales Pisa to the Rangers for Cory Cross and Radek Dvorak. Cross would play over 100 games in Edmonton before getting dealt to the Penguins for Dick Tarnstrom. Both he and Dvorak would be solid depth players on the Oilers’ 2006 team.

Doug Lynch and Jeff Woywitka, the defence prospects Edmonton got through trading Guerin and Comrie, ended up being packaged along with Eric Brewer in a trade for Chris Pronger. He and Ales Hemsky were two of the most important players on that 2006 team.

The Arnott trade chain continues through Pronger because of the Lynch connection, but that’s something that’s been discussed at length already. If you read my Mark Messier trade post, you can pick up the Pronger part and see that it’s resulted in Andreas Athanasiou, so that’s the same here too. The key we’ll be focusing on here is Hemsky.

Hemsky was an excellent player for the Oilers throughout the 2000s. After being drafted 13th overall in 2001, Hemsky broke into the league in the 2002-03 season, posting six goals and 30 points in 59 games. He would put together a decent sophomore season in 2003-04, spend the lockout year in Europe, and then enjoy a breakout year in 2005-06, scoring a team-leading 77 points.

After that, Hemsky’s legacy in Edmonton gets muddled up a little bit. Partially because the team wasn’t good and partially because he dealt with so many injuries, many forget just how good Hemsky was. His hands, his vision, and his shot were all top-notch, but that 2006 team was really the only good Oilers team was ever a part of.

Hemsky stuck around in Edmonton for a long time, scoring 142 goals and 477 points over 652 games. The team might have hung on a little too long, though. There was plenty of talk about dealing Hemsky away as the team was going through their Oil Change tanking years, but it didn’t happen until 2014 when Hemsky was a shell of his former self. All the Oilers would get in return for arguably their best player of the 2000s was a third- and fifth-round pick.

Lost in the excitement of drafting Connor McDavid with the first pick in 2015 was the under-the-radar acquisition of Cam Talbot, the understudy of Henrik Lundqvist who had thrived as a backup in New York. The Oilers sent that third they acquired from Ottawa for Hemsky along with two other draft picks to acquire Talbot.

Ironically, the Oilers also acquired another goalie a few weeks later, Anders Nilsson, to share the net with Talbot. Edmonton moved Liam Coughlin, the guy they drafted with the fifth-round pick they got from Ottawa for Hemsky, to Chicago for Nilsson. More on that in a minute.

Talbot would play a key role in helping return Edmonton to the playoffs in 2017. After a decent showing in 2015-16, Talbot would put up one of the best seasons seen by a goalie in franchise history in 2016-17. Talbot started a whopping 73 games for the Oilers that season, posting a .919 save percentage. He set the franchise’s single-season record for games played, wins, and saves that season.

Talbot would fizzle out over the next couple of seasons after that, but his importance to the 2017 team is undeniable. He would end up getting dealt to the Flyers for Anthony Stolarz ahead of the 2019 trade deadline, who left as a free agent shortly after.

Flipping back to Nilsson to finish things off, he remains our one final connection to Jason Arnott. Nilsson played just 26 games for the Oilers before being traded to St. Louis for prospect Niklas Lundstrom and a fifth-round pick in 2016, which Edmonton used on Graham McPhee. McPhee doesn’t have a contract with the Oilers and he just put up 12 points in 34 games playing for Boston College, so I think this might be the end of the line for the Arnott trade tree.

Arnott helped the Oilers get back into the playoffs in 1997, his trade directly helped the Oilers make a run to the Cup Final in 2006, and it also helped them get back into the playoffs after another long hiatus in 2017. That’s a pretty good run.