Former NHL General Manager Claims Critical Offseason Mistake by Stan Bowman Last Summer May Have Ultimately Cost the Edmonton Oilers a Shot at Winning the Stanley Cup.

Former NHL general manager Mike Gillis has sparked considerable debate in the hockey world with his recent comments about a critical misstep made by Stan Bowman during the previous offseason—one he believes may have derailed the Edmonton Oilers’ chances of winning the Stanley Cup. While the Oilers came heartbreakingly close, ultimately falling short in the Finals, Gillis contends that the seeds of that disappointment were sown months earlier, and that one particular decision—or lack thereof—might have been the turning point that cost Edmonton their long-coveted championship.

According to Gillis, the Oilers were on the brink of becoming a true dynasty-level team. With generational talents like Connor McDavid and Leon Draisaitl, along with a surging supporting cast and a competent coaching staff, Edmonton had every piece in place to make a dominant playoff run. In fact, many insiders felt the 2024–25 campaign was Edmonton’s best shot at claiming the Cup since their glory days of the 1980s. But Gillis argues that a single oversight in the 2024 offseason, connected to the involvement of Stan Bowman, played a crucial role in undermining that quest.

Bowman, the former longtime general manager of the Chicago Blackhawks, had stepped back into the NHL conversation in advisory and informal consulting roles after his controversial exit from Chicago. Though never officially named as part of Edmonton’s front office, sources indicated that Bowman had provided strategic input during key moments of the Oilers’ offseason planning. Gillis believes that Bowman’s influence led to a significant miscalculation in roster construction—one that created a depth issue that became glaringly obvious during the team’s final playoff push.

Specifically, Gillis points to Edmonton’s failure to adequately address their third-pairing defensive depth and bottom-six forward resilience. According to him, there were opportunities—viable, affordable ones—to solidify both areas. He says Bowman advised against making certain signings or trades that would have bolstered the roster, instead encouraging the team to rely on internal options and unproven prospects. While the decision may have saved cap space in the short term, it left Edmonton vulnerable when injuries and fatigue inevitably hit during the playoffs.

“Stan’s track record in Chicago was built on elite top-end talent, but also on veterans filling depth roles,” Gillis explained. “What surprised me is how different his advice seemed to be in Edmonton. There were players available last summer who could have played critical minutes in the playoffs—guys like Ilya Lyubushkin, Erik Haula, or even a returning Mattias Janmark in a stronger role. They passed on those types of moves. That hesitation, in my opinion, cost them when it mattered most.”

One of the key moments Gillis points to is the Oilers’ Game 5 loss in the Stanley Cup Final, where their third defensive pairing was exposed multiple times by a relentless forecheck. That game swung momentum firmly in favor of their opponents, who went on to clinch the series in Game 6. Injuries to top-pair defensemen forced the Oilers to rely heavily on depth players who simply weren’t equipped to handle the intensity of the Finals. Gillis suggests that better preparation during the offseason would have prevented that collapse.

“You don’t build a Cup-winning team on talent alone,” Gillis continued. “You win championships by anticipating adversity and building around it. Edmonton had the skill. What they didn’t have—because of a missed opportunity last summer—was the depth to weather the storm.”

Some fans and analysts have pushed back against Gillis’s comments, arguing that hindsight makes all mistakes look clearer than they are. After all, Bowman wasn’t officially hired by Edmonton, and his role—if any—was informal. But others are echoing Gillis’s concerns. A number of hockey writers have noted that Edmonton’s offseason strategy felt incomplete, especially for a team in win-now mode. Despite McDavid and Draisaitl both putting up Hart Trophy-worthy seasons, the roster behind them looked one injury away from disaster—and that disaster came at the worst possible time.

There’s also the broader question of Bowman’s influence and whether his reputation as a “championship architect” blinded Edmonton’s brass to the realities of the modern NHL. Bowman, of course, helped lead Chicago to three Stanley Cups in the 2010s, but his final years in Chicago were marked by bloated contracts, questionable trades, and a sharp decline in organizational depth. That history, some argue, should have been a warning sign rather than a reason to trust his input.

“Bowman’s time in Chicago was complicated,” said one anonymous executive from a Western Conference rival. “Yes, he won. But how much of that was him, and how much of that was inherited talent and a strong coaching staff? Edmonton put a lot of faith in advice from a guy who hadn’t built a successful team in nearly a decade. That’s a risky bet.”

The Oilers themselves have remained silent on the issue. General Manager Ken Holland, now in an executive advisory role, has not commented on Gillis’s claims. Head coach Kris Knoblauch, meanwhile, has focused on the positives from the season, stressing that the team’s core remains intact and that their window to win is still wide open. But within the fanbase and among analysts, Gillis’s remarks have reopened difficult questions about the decisions that shaped the 2024–25 season.

Should the Oilers have pushed harder to acquire depth via trade? Did they lean too heavily on internal development and mid-tier veterans? Were they too conservative in free agency? And, most importantly, should the team have relied—whether officially or not—on input from someone like Bowman, whose most recent track record is, at best, mixed?

Even some Oilers players have subtly hinted at frustration with the roster’s depth. In post-game interviews following their Finals exit, a few veterans mentioned the challenges of playing heavy minutes without much relief. While no one has directly criticized management, the subtext was clear: the team was top-heavy, and that imbalance became costly down the stretch.

Adding to the intrigue is the fact that several players Edmonton reportedly passed on last summer went on to play key roles on playoff teams. Erik Haula had a breakout postseason, helping his team advance deep with clutch faceoff wins and penalty-killing contributions. Ilya Lyubushkin brought grit and reliability on the blue line for a contender. These were not expensive acquisitions, but they were the kind of veteran depth moves that often define a team’s playoff fate.

Gillis’s comments come at a crucial time for the Oilers, who are now preparing for another run and facing difficult decisions about the future of their roster. With Draisaitl’s contract situation looming and McDavid’s prime years continuing to tick by, the margin for error is vanishingly small. Edmonton can’t afford another summer of hesitation or misjudged strategy. If they’re to finally raise the Cup again, every offseason move must be executed with precision.

And that, Gillis warns, is the true lesson of Bowman’s alleged mistake.

“This team isn’t going to have ten more chances,” Gillis concluded. “They might have two, maybe three if things break right. Every decision counts. Every summer matters. And if you let a single offseason slip away because you’re listening to the wrong people or chasing outdated formulas, it can cost you everything. The Oilers learned that the hard way.”

Whether or not the front office agrees with Gillis, his remarks have reignited an urgent conversation in Edmonton: What went wrong? Who holds responsibility? And most importantly, how can they make sure it doesn’t happen again?

If the Oilers are to avoid repeating history, they’ll need to learn from every misstep—real or perceived—and ensure that this summer, every roster move aligns with the only goal that matters: bringing the Stanley Cup back to Edmonton.