Team

Betting

OilersNation has no direct affiliation to the Edmonton Oilers, Oilers Entertainment Group, NHL, or NHLPA

Oilers bold predictions: Stan Bowman swings big before trade deadline

By Ryley Delaney

Sep 16, 2026, 11:00 EDTUpdated: Sep 16, 2026, 11:38 EDT

Comments

The Edmonton Oilers are running out of time to win Connor McDavid a Stanley Cup.

In January 2027, McDavid will turn 30 years old. While unlikely to decline, at least for another half-decade, the Oilers need a sixth Stanley Cup soon. McDavid’s contract is set to expire following the 2027-28 season, and if they wish to avoid a Decade of Darkness version two, they may need to trade him as soon as next off-season.

The pressure is on to win this season, it’s basically Stanley Cup or bust for the organization. They’ve made notable moves in the off-season, as has been the case for most of the 2020s, but now it’s time for the Oilers to swing big at the trade deadline.

A bold prediction for this season is the Oilers finally land a big fish before March 1st’s trade deadline.

A history of a buying deadline in the McDavid era

The Oilers have missed the postseason just three times since drafting Connor McDavid. They missed in 2016, ended the Decade of Darkness in 2017, before two more disappointing misses in 2018 and 2019. Thanks, Peter Chiarelli.

Every other season, they’ve made the playoffs, ranging from disappointing first-round exits, good showings, and heartbreaking defeats in the Stanley Cup Finals.

Despite making the playoffs in eight of the last 11 seasons, you’d be hard-pressed to find a trade deadline where the Oilers truly went for it. The closest example is when they acquired Mattias Ekholm from the Nashville Predators, trading their first-round pick for the first time in decades.

Other than that season, it’s been nothing but depth additions. In 2017, they acquired David Desharnais. In 2020, in Ken Holland’s first season as the General Manager, the Oilers acquired Tyler Ennis, Mike Green, and Andreas Athanasiou. It was much of the same in 2021 and 2022, acquiring Dmitry Kulikov in the former and Brett Kulak and Derick Brassard in the latter.

After landing Ekholm before the 2023 trade deadline, the Oilers made another depth add before the 2024 trade deadline, landing Sam Carrick and Adam Henrique from the Anaheim Ducks, as well as Troy Stecher from the Arizona Coyotes.

Despite Holland departing for worse pastures following the 2023-24 season, his successor Stan Bowman hasn’t done much either. Before the 2025 deadline, he acquired Jake Walman from the San Jose Sharks and Trent Frederic and Max Jones from the Boston Bruins. This past deadline, Bowman acquired Connor Murphy, Colton Dach, and Jason Dickinson from the Chicago Blackhawks in two separate trades.

Most of these trades, aside from the 2020 trade deadline, are solid moves that helped the Oilers contend. But aside from the 2023 trade deadline when they acquired Ekholm, they haven’t landed a big fish.

That’ll change this season.

The pressure is on

The Oilers’ championship window, as it stands, is two years at best. McDavid signed a team-friendly contract that carries a cap hit of $12.5 million during the 2025 off-season, with it officially kicking in this past off-season. The bad news is that it’s worth just two years.

After a disappointing first-round exit, the Oilers have two more cracks at this before McDavid enters free agency. If they wish to keep McDavid a lifetime Oiler, there can’t be another first-round exit, and honestly, it may be Cup or bust.

If they don’t win the Cup and McDavid enters 2027-28 without an extension, there’s a very real possibility that the Oilers look to move him. No matter who they trade him for, they lose that trade, but at least you get something for the best player of all-time.

The Oilers need to go for it; it’s as simple as that. Depth additions are nice, and a lot of those trade deadline moves have panned out well for the team. That said, whatever their biggest need is before the trade deadline, they need to fill it with the best player available on the trade wire.

Who could be available?

Predicting who could be available for a trade six months from now is difficult, much less where teams will be in the standings before the season even starts. Hell, even knowing the Oilers’ biggest need before the season even starts is a shot in the dark as well.

Still, there are a handful of notable players set to become unrestricted free agents following the 2026-27 season. On teams likely to contend, Jason Robertson, Nikita Kucherov, and Quinn Hughes are on expiring deals.

Robertson has been involved in trade rumours for a while now, and if he doesn’t appear to re-sign, trading him to recoup assets may be the Dallas Stars’ best move. The same logic can be applied to Hughes. The chances that Kucherov is traded are slim to none at this point, but if the Lightning end up having a tough season, he’d easily become the best player available on the market.

Other notable skaters on expiring deals are Pittsburgh Penguins’ Sidney Crosby, Detroit Red Wings’ Alex DeBrincat, Seattle Kraken’s Vince Dunn, Nashville Predators’ Ryan O’Reilly, and Boston Bruins’ Casey Mittelstadt. They range from incredibly unlikely to be traded (Crosby) to definitely on the move if the team sells (DeBrincat).

This doesn’t even mention players with term left, much like how Ekholm still had four years left on his deal. Connor Hellebuyck and Dylan Larkin requested trades this off-season, though it’s unlikely that the American-born players wish to join or remain on a Canadian team. Elias Pettersson and Alexis Lafrenière are in need of a change of scenery, and who knows if they become available.

Filip Forsberg, Mathew Barzal, Owen Tippett, and Bobby McMann are four players approaching or are already in their 30s who are also top-six forwards. Perhaps one of these players could be shipped out before March 1st’s deadline.

The Los Angeles Kings acquired Artemi Panarin before the 2026 deadline, with the veteran winger signing a two-year deal with the Kings. If they have another rough season, could he be moved? What about David Pastrňák, Kirill Marchenko, or Mika Zibanejad?

Will all these players be available? No, but if there’s even a chance the Oilers have a chance to land a game-changer, it’s something that has to be done.

What assets do the Oilers have to offer

One area of concern is that the Oilers have one of the weakest farm systems in the National Hockey League with limited draft picks. That hasn’t stopped other contenders from acquiring big names before the deadline.

Before the 2026 trade deadline, the Colorado Avalanche acquired Nazem Kadri for a first and a second, a mid-tier prospect in Max Curran, and a struggling veteran in Victor Olofsson. Kadri has term on his contract, and the Oilers had the assets to match that package. Similarly, the Flames sent MacKenzie Weegar to the Utah Mammoth for a prospect, a player with a sizable cap hit, and three 2026 second-rounders. Like Kadri, Weegar’s contract extended past the 2025-26 season.

Panarin was the big soon-to-be free agent moved before the 2026 deadline for prospect Liam Greentree (selected in the late first round), a 2026 third, and a 2028 fourth. Even with limited assets, the Oilers could’ve matched those trades. An added benefit for the Oilers is that they’ll be accumulating cap space ahead of the 2027 trade deadline, something not every contender has the ability to do.

Simply put, they have to swing big before the 2027 trade deadline. The pressure is on, and there’ll surely be a top-six forward or top-pairing defenceman available before the deadline.

Ryley Delaney is a Nation Network writer for DFOEdmonton, DFOCalgary, and Blue Jays Nation. Follow her on X at @Ryley__Delaney.

PRESENTED BY CAPITAL GMC BUICK

Hockey fans recognize elite performance instantly, and that’s exactly how Capital GMC Buick operates. With one of the city’s deepest selections of top-quality GMC and Buick vehicles and a customer experience built to win year after year, this dealership consistently leads the pack. Five current NHL players proudly drive vehicles from Capital GMC Buick, and for good reason. The store has been rated the #1 GM dealership in Canada by DealerRater for three consecutive years, is the only GM dealer in Edmonton endorsed by J.D. Power as a Dealer of Excellence, and has raised over $30,000 for the Stollery Children’s Hospital.