Throughout the summer and into the fall, we’ll be counting down the days until the Edmonton Oilers begin their 2023-24 season with a daily trip down memory lane. Today at 89, we have Mike Comrie, a local talent who went from being a hometown in Edmonton hero to a villain because of a contract holdout.

The Oilers selected Comrie in the third round of the 1999 NHL draft, a couple of years after they acquired his older brother, Paul, in a trade with the Tampa Bay Lightning. The two Comrie brothers were well-known around Edmonton not just because of hockey, but because their father, Bill, was one of the co-founders of The Brick, a furniture company that wound up selling for $700 million in 2012.

Comrie made a name for himself as a top prospect when playing in the Alberta Junior Hockey League. He won the Rookie of the Year in 1996-97 and followed that up in 1997-98 with one of the best seasons in the league’s history. Playing for the St. Albert Saints, Comrie scored 60 goals and 138 points over 58 regular-season games and added 48 points in 19 playoff games.

After scoring 44 points in 42 games as a freshman at the University of Michigan in 1998-99, Comrie was selected by his hometown club with the No. 91 overall pick in that summer’s draft. Comrie had first-round talent but he fell to the Oilers in the third round because other teams were worried he wasn’t big enough to have success at the NHL level.

Comrie spent one more season with Michigan and then joined the Kootenay Ice of the Western Hockey League for the 2000-01 season. He scored a whopping 79 points over 41 games for the Ice and then inked an entry-level contract with the Oilers in late December.

Comrie used a loophole that had previously been established by defenceman Mike Van Ryn to sign a contract worth much more than other players who were breaking into the league.

Since Comrie left American college and played a season in the WHL as an over-ager, he was considered a free agent and wasn’t bound to the $1.13 million maximum base salary that had been set for drafted players that year. His deal with the Oilers was worth $10 million over three years, which roughly $7 million of that money coming through bonuses.

Comrie scored 22 points in 44 games after joining the Oilers for the second half of the 2000-01 season and then broke out in 2001-02 with 33 goals and 60 points, good for the team lead in both categories. He followed that up in 2002-03 with 20 goals and 51 points, though he drew some criticism after scoring only one point in six playoff games.

The three-year, entry-level contract Comrie signed with the Oilers came to an end that summer and he sought a significant raise as a restricted free agent. Comrie rejected Edmonton’s qualifying offer, which would have seen him earn a standard 10 percent increase on his $1.13 million base salary from the previous contract, and he then requested a trade when he was held out of the team’s training camp in the fall.

The Oilers had a deal in place with the Mighty Ducks of Anaheim in December that would have seen 2003 first-round pick Corey Perry and a first-round pick in the 2004 draft sent to Edmonton in exchange for Comrie. The deal fell through because Oilers general manager Kevin Lowe wanted Comrie to reimburse around $2.5 million to the Oilers from the bonus money he had earned.

Both sides were criticized during this ordeal. Comrie was called a “spoiled brat” for abandoning his small-market, hometown team over money despite being the heir to an incredible fortune while Lowe and the Oilers were referred to as “vindictive” for throwing a wrench into a deal that appeared to be a win for everyone.

A few days later, Comrie was traded to the Philadelphia Flyers in exchange for Jeff Woywitka, a defenceman who was selected in the first round of the draft a couple of years earlier, along with a first-round pick in the 2004 draft and a third-round pick in the 2005 draft. Edmonton wound up selecting London Knights standouts Rob Schremp and Danny Syvret with those two picks.

Comrie played only 21 games in Philadelphia before the Flyers moved him to the Phoenix Coyotes for veteran goaltender Sean Burke and young forwards Branko Radivojevic and Ben Eager. He made his return to Edmonton in March and was booed mercilessly by fans in what wound up being a 5-4 overtime win for the Oilers.

After spending the lockout season in Sweden, Comrie returned to the Coyotes in 2005-06 and scored 30 goals and 60 points. The following season, Comrie was traded to the Ottawa Senators and he helped the team reach the Stanley Cup Final for the first time. The Sens were beaten in five games by the Anaheim Ducks, the team that nearly acquired Comrie a few years earlier.

Comrie’s career wound up getting cut short by injuries as he opted to retire in 2011 following his third hip surgery. He came back to Edmonton on a one-year contract for the 2009-10 season and had fans chanting his name when he assisted on four goals and got into a fight during a 4-0 pre-season win. Unfortunately, a bout with mono limited Comrie to only 43 games during the regular season.

With 168 goals and 365 points over 589 games, Comrie had a successful career in the NHL, but his story is one that’s loaded with thoughts of what could have been. Could he have become an all-time Oilers great had he stayed in Edmonton longer? Could he have won the Stanley Cup if Kevin Lowe let that deal with Anaheim happen?