It’ll be somewhat of an unusual night in Montreal as the Edmonton Oilers are scheduled to select at No. 29 overall in the NHL draft, which is the latest they’ll be making their top pick in well over a decade.

There’s also no guarantee that No. 29 overall is where the Oilers will be drafting. The team is in win-now mode and their first-round pick could be moved to acquire a player to help the team right now. There’s also a possibility that the Oilers could trade down to stockpile more draft picks, as they don’t currently own picks in the second, third, and fourth rounds.

The Oilers just went on their deepest playoff run of the Connor McDavid and Leon Draisaitl era and there’s no better time than now to go all-in on trying to win. Getting swept by the Colorado Avalanche in the Western Conference Final showed that the Oilers have quite a bit of work to do in order to hang with the league’s elite teams. They badly need a legitimate starting goaltender and they could use some more scoring depth and help on the blueline.

The last time the Oilers traded away their first-round pick was all the way back in 2006 when the team acquired Dwayne Roloson from the Minnesota Wild at the trade deadline. If the Oilers could move the No. 29 overall pick for a player anywhere near as impactful as Roloson was, they’d do it in a heartbeat.

The challenge is that the Oilers don’t have very many picks in this year’s draft, so trading the No. 29 overall pick would essentially leave them with an empty draft class beyond late-round flyers.

This is something we’ve seen Ken Holland do multiple times in his tenure as the general manager of the Oilers.

Back in 2020, the Oilers moved their third-round pick to the San Jose Sharks for picks in the fourth and fifth rounds. The swap resulted in Edmonton getting Carter Savoie and Tyler Tullio, two quality forward prospects.

Holland has also shown that he’s willing to trade down in the first round. Last summer, the Oilers traded the No. 20 overall pick to Minnesota and got back the No. 22 and No. 90 overall picks in return. The Wild moved up to select goaltender Jesper Wallstedt while the Oilers took Xavier Bourgault and Luca Munzenberger.

It makes a lot of sense for the Oilers to trade down because the team doesn’t have another pick until the fifth round and having more bullets in the second and third rounds would be helpful for the Oilers to continue to add depth to their system. But on the other hand, many teams get burned when they trade quality for quantity. Back in 2003, the Oilers traded down to select Marc-Antoine Pouliot and J-F Jacques and gave up the pick that was used on Zach Parise. Maybe going with the best player available is the right move.

This year’s draft is going to be a bit of a crapshoot because both player development and team scouting have been limited by the pandemic for over two years now.

Seasons have been postponed and delayed, tournaments have been canceled, and travel restrictions have ultimately limited the access that scouts have to watch players. Many Canadian players in this year’s draft class are ones who were set to play their first CHL seasons in 2020-21, the year that was almost completely derailed due to COVID-19.

When you put it all together, a lot of prospects are going to be a little behind where they’d normally be at their given age and teams might also have less intel in certain areas than usual. All 32 teams’ draft lists are going to be wildly different and there will be a lot of off-the-board picks this year, so simply waiting and going with who they deem to be the best player available at No. 29 overall could net the Oilers a very good prospect.

The reality of the salary cap world is that teams need to constantly be internally developing quality talent on inexpensive contracts and the No. 29 overall pick is Edmonton’s best bet at finding a player who can do that for them in the future.

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