The Worst NHL GMs: A Look at Long-Serving Disasters (2026)

The NHL's Longest-Serving GM Disasters: A Controversial Countdown

The world of sports is filled with intriguing questions, and some of the most captivating ones are those that seem simple on the surface but reveal a complex web of factors when you dig deeper.

Today, we're tackling a question that might seem straightforward: Who was the worst NHL general manager to keep their job for five years or more? But as we'll see, this query opens a Pandora's box of controversial opinions and historical what-ifs.

In a league where results are everything, it's expected that underperforming GMs will be swiftly replaced. Yet, occasionally, teams stick with a GM long past the point of diminishing returns. These are the stories we're exploring today, as we count down the 10 worst GMs who managed to stay in the same role for at least half a decade.

  1. Mike O'Connell, Boston Bruins (2000-2006): O'Connell stepped into the daunting task of replacing a legend, Harry Sinden. While his Bruins had some regular-season success, they never advanced in the playoffs. His most infamous move was trading Joe Thornton, a future MVP, for a package that included Wayne Primeau and Marco Sturm. This trade is now considered one of the worst in NHL history.

  2. Glenn Sather, New York Rangers (2000-2015): Sather, a Hall of Famer with the Oilers, had a long tenure in New York. He's remembered for his infamous quote about never losing with the Rangers' payroll, but the team struggled in his early years. Sather signed numerous bad UFA contracts, and while the Rangers improved later, many fans recall the initial struggles.

  3. Max McNab, Washington Capitals (1975-1981): McNab took over an expansion team with a terrible first season. Despite high draft picks, the Caps never finished with more than 70 points in his tenure. However, he did draft future star Mike Gartner.

7.5. Ron Francis, Seattle Kraken (2019-2023): Francis was the Kraken's first GM, but his role was limited during the team's initial years. He was promoted to president in 2023, but his expansion draft strategy was criticized for a lack of significant moves. He did acquire two first-round picks for Yanni Gourde.

  1. Michael Barnett, Arizona Coyotes (2001-2007): Barnett's Coyotes made the playoffs in his first year but declined afterward. He traded young star Danny Briere, and the team struggled during his tenure, partly due to external factors.

  2. Doug MacLean and Scott Howson, Columbus Blue Jackets (1998-2013): These two GMs oversaw a single playoff appearance with no wins. MacLean drafted Rick Nash, but Howson later traded him. Howson received a GM of the Year vote despite being fired early in the season.

  3. Gerry McNamara, Toronto Maple Leafs (1981-1988): Working for notorious owner Harold Ballard, McNamara had little chance. He made some unpopular moves, like trading Darryl Sittler, but also drafted Wendel Clark. The Leafs' struggles were more about Ballard's mismanagement than McNamara's decisions.

  4. Rejean Houle, Montreal Canadiens (1995-2000): Houle had playoff success early, but he's infamous for trading Patrick Roy, one of the greatest goalies, just weeks into his tenure. This move, and others like trading captain Pierre Turgeon, overshadowed his achievements.

  5. Kevyn Adams, Buffalo Sabres (2020-present): Adams has overseen a period of fan unrest and no playoff appearances. His handling of the Jack Eichel trade and the team's overall direction have been criticized.

  6. Jim Benning, Vancouver Canucks (2014-2021): Benning's Canucks made the playoffs twice but finished under .500 in other years. He's known for disappointing drafts and the failed promise of being 'almost there.'

  7. Mike Milbury, New York Islanders (1995-2006): Milbury was unafraid to make big moves, but many backfired. He traded young stars like Roberto Luongo and Jason Spezza, and his teams missed the playoffs in most seasons. The Milbury era is a cautionary tale for Islanders fans.

And now, the controversy:

  • Should Ron Francis be on this list? His role as GM was limited during the Kraken's initial years, and his promotion to president might suggest a different evaluation.
  • Is it fair to judge GMs like Max McNab and Michael Barnett, who faced significant external challenges?
  • How much blame should be placed on GMs like Gerry McNamara, who worked for notoriously difficult owners?

These questions don't have easy answers, and they're part of what makes sports history so fascinating. Share your thoughts in the comments, and let's keep the conversation going!

The Worst NHL GMs: A Look at Long-Serving Disasters (2026)
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