The Edmonton Oilers made the wrong call when they named Stan Bowman as the organization’s new general manager. Almost two years later, the franchise continues to decline under Bowman’s guidance.

The Oilers’ descent is only being expedited as the 2026 NHL Trade Deadline nears. Bowman struck again, pulling off his second deal with the Chicago Blackhawks in the past few days. After bringing in veteran defenseman Connor Murphy, the two squads linked up again for another trade, sending forwards Jason Dickinson and Colton Dach to Edmonton in exchange for additional draft picks.

On one hand, you have to applaud Bowman’s aggressive pursuit of improvements. Since taking over the position, he’s relentlessly tried to fix the issues plaguing the Oilers. But his execution on that is anything but impressive. If anything, Bowman is ruining Edmonton’s Stanley Cup chances for both this season and beyond.

How Many Trades Can You Lose?

Things started fine under Bowman. He shook up the forward group, bringing in players like Vasily Podkolzin and Matthew Savoie. At the 2025 NHL Trade Deadline, he swung for the fences by acquiring Jake Walman and Trent Frederic.

One of those trades was great. The deal for Walman was a fair price and they were able to extend the talented two-way defender. The other trade, and subsequent decision to extend Frederic, however, was a horrific mistake.

That kickstarted a chain of bad moves for the Oilers that Bowman can’t get out of. They stupidly acquired goaltender Tristan Jarry and the rest of his bloated contract while sending out a competent, more accomplished goalie in Stuart Skinner.

This most recent move for Dickinson and Dach takes the cake. It’s been two seasons since Dickinson scored a career-best 22 goals. That was the only season he ever reached double digit totals in goal. The reality is that he’s an incredibly strong defensive fourth-line center. He certainly improves their overall team defense and penalty killing units, but what is that worth?

To Bowman, it’s apparently worth a future first-round pick. They don’t have the 2026 one, which was already traded away for Walman. They did have their 2027 and 2028 first-round picks, but one of those will go to Chicago in exchange for Dickinson and Dach. Chicago Tribune writer Kalen Lumpkins detailed the conditions of the draft picks involved, and it makes zero sense for Edmonton.

As Lumpkins explains, the Oilers can choose to give their 2027 first-round pick to Chicago, but it is a top-12 protected pick. That means if Edmonton finishes with a pick in the top 12, they will keep that pick and automatically send their 2028 first-round pick to Chicago. Alternatively, if the Oilers trade their 2028 pick before next year’s Trade Deadline, the 2027 pick automatically converts to the Blackhawks.