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........

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