It has been 11 seasons since Edmonton drafted Connor McDavid first overall in 2015, and the Oilers captain is still without a Stanley Cup ring. As we approach what could be the end of the McDavid era in Edmonton — if next year is not his final season, it is possible the year after that will be — it is time to examine what Oilers ownership and management did with its winning lottery ticket.
If McDavid never wins a championship in Edmonton, it will be fair to argue that the gift has been squandered, that despite one of the greatest head starts in hockey history, Oilers brass could not get it done. If they do build a championship team around their centrepiece, then the critics will be silenced forever.
The Good
For starters, ownership and management kept McDavid and Leon Draisaitl in the fold, extending both to long-term contracts. Same with Evan Bouchard. Edmonton used to be a place where veterans never stayed long and free agents avoided. Owner Daryl Katz treats his players well and spends to the cap. Players want to stay and come here — a huge difference from the Chris Pronger era.
Despite heavy criticism, the Oilers are one of the most successful NHL teams over the last four seasons: three trips to the Western Conference Final and consecutive trips to the Stanley Cup Final. Only one other club has been that good over that span.
Zach Hyman's free agent signing was Ken Holland's handiwork, resulting in one of the best bargains in the league. A player averaging just under 40 goals a year on a seven-year contract at $5.5 million per year is rare. What were the Toronto Maple Leafs thinking?
The Vasily Podkolzin trade: Stan Bowman sent a fourth-round pick to Vancouver for a top-six forward who is also the toughest player on the team. Podkolzin is an ultimate team guy and was Edmonton's best player in the 2026 playoffs, with more to come.
Getting Cam Talbot in June 2015: Peter Chiarelli acquired Talbot from the New York Rangers for second- and third-round picks. Talbot was Edmonton's starter for four years and helped end their 10-year playoff drought in 2016-17.
The Mattias Ekholm trade: Ken Holland gave up Tyson Barrie, Reid Schaeffer, a first-round pick (24th overall), and a fourth-round pick, but Ekholm proved to be a major defensive pillar. His presence enabled Bouchard to reach a new level.
The Bad
Despite these successes, there have been notable missteps. The Oilers have struggled to build a complete roster around McDavid, often lacking depth scoring and reliable goaltending. The team's salary cap management has been questioned, with some contracts hampering flexibility. Additionally, the team has faced criticism for its defensive system and special teams performance at critical moments.
The Ugly
The ugly side includes the failure to win a Cup despite having the best player in the world. The 2023 playoff collapse against the Vegas Golden Knights, where the Oilers blew a 3-2 series lead, remains a painful memory. The constant turnover in coaching staff and front office has also created instability. If McDavid leaves without a championship, the legacy of this management era will be one of wasted potential.
