If you recall just a few years back as general manager of the Edmonton Oilers, Ken Holland said arguably his most infamous quote "I don't think that you can be all-in every year. I think you pick and choose."
This quote encapsulates his tenure as GM of the Oilers well, refusing to do what is necessary to win a Stanley Cup, instead there were plenty of half-baked solutions where instead of dropping multiple picks and prospects on acquiring a big fish, he attempted to shore up the depth.
This conservative approach can be useful in some situations but we would not be here today, only a day after franchise player Connor McDavid signed only a two-year commitment, if it was successful.
However, since Holland and the Oilers mutually agreed to part ways, the M.O. of the club seems to be much different. In the words of Mike Ehrmantraut from Breaking Bad "No more half measures".
Bowman looks to make a big splash
After the big news of Monday broke with McDavid signing his extension, the Oilers GM joined Bob Stauffer on his program Oilers Now to give an interview. During the conversation Stauffer let slip some very interesting tidbits.
He revealed that Bowman told him when speaking about trading draft picks "If we move first or second round picks for players we are gonna do our best to ensure there is term length left on the players or we extend the players."
He then brought up examples of this with the Oilers trading prospect Shane LaChance to the New Jersey Devils for Trent Frederic and a first round pick to the San Jose Sharks for defenceman Jake Walman. To add to this, similar ideas applied with the trade for Ike Howard this summer where the club traded former first round pick and top prospect, Sam O'Reilly.
If the team wants to make a big move like the aforementioned Frederic and Walman trades, this would be huge for the Oilers and their cup chances. This is also made especially more possible with the hometown discount that McDavid re-signed for.
Oilers hope to add a top-six forward
There are rumours that the team is still hoping to add to their top-six forward group with NHL insider Pierre LeBrun from TSN reporting last week that the team offered a contract to the top free agent remaining, Jack Roslovic but that he did not want to sign.
""We believe he had a deal on the table from the Oilers and it didn't interest him.""Pierre LeBrun, Overdrive
If true, this means that the Oilers will have to look elsewhere to add to their forward group, likely through the trade market in season or next off-season.
If Bowman is able to identify a target and work on a trade, he will have plenty of assets at his disposal according to Puckpedia.com. As of right now the team has two first round picks (2027 and 2028) as well as second and third round picks in for the next three years (2026, 2027, and 2028).