Oilers GM Ruining Stanley Cup Chances

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.

Conditions of the 1st round pick the Blackhawks received in the Dickinson/Dach trade:

If the Oilers pick top 12 in 2027, the pick slides to 2028 unconditionally

If the Oilers trade their 2028 pick before the 2027 trade deadline, the Hawks would get the 2027 pick…
— Kalen Lumpkins (@kalenalumpkins) March 5, 2026

Don't Forget About the Offer Sheets

Does everyone remember one of the first actions Bowman took as GM in Edmonton? As a refresher, he inherited two difficult restricted free-agent situations with defenseman Philip Broberg and forward Dylan Holloway. The team spent first-round picks on both players in recent years, but both needed new contracts.

Instead of signing them to deals that were more than fair and reasonable for their salary cap situations, Bowman let both walk and accepted the draft pick compensation from the St. Louis Blues.

The Oilers could really use both Holloway's offensive production and Broberg's two-way impact on the blue line.

Just this season alone, the Oilers have dealt away Stuart Skinner, Brett Kulak, their first round picks in 2026 and either 2027 or 2028 and Sam O'Reilly. In return, they've brought in Isaac Howard, Tristan Jarry, Sam Poulin, Jason Dickinson, Colton Dach, Connor Murphy, Spencer Stastny and Connor Ingram.

Not only is that an unimpressive return for what they've given up, it's made the team worse. They are not any closer to the Stanley Cup. If anything, they are a worse version of the teams that went to the Stanley Cup Finals in back-to-back seasons. That's all thanks to the awful work of general manager Stan Bowman.

Make sure you bookmark Breakaway On SI for the latest news, exclusive interviews, recruiting coverage, and more!