The Shocking Truth Behind the NHL’s Longest-Tenured Worst GM Revealed

You know, some sports questions seem to pop up like they’re straightforward puzzles — but dig a little deeper, and they’re anything but simple. I’ve spent way too much time chasing threads about jersey numbers and concocting rosters packed with the worst contracts that somehow still fit under the salary cap. Well, today I’m diving into one of those deceptively tricky queries once again. Here’s the kicker: which NHL general manager endured the most painfully disastrous tenure with a single team that lasted five years or more? Sounds like a slam dunk, right? Not quite. The league’s relentless demand for results usually means those who falter get shown the door way before the half-decade mark. Yet, every now and then, a franchise inexplicably clings to a GM well past the point of reasonable hope. That’s the fascinating—and frustrating—category we’re unraveling here, as we rank the ten worst long-term GM stays in NHL history. Ready for some eye-opening surprises? Let’s get into it. LEARN MORE

I’m a big fan of sports questions that seem simple but are actually more complicated than they appear, which is how I’ve managed to waste huge chunks of my life on questions about jersey numbers or building rosters of terrible contracts that are still somehow cap compliant. Today, we’re going to try another one.

Which GM had the worst long stint with a team, meaning five years or longer?

You can already see the problem. There are lots of GMs in NHL history who’ve held the role for a particular team for a long time. And there are lots of GMs who didn’t do an especially great job. But those two groups aren’t supposed to overlap. This is supposed to be one of the most important jobs in a relentlessly results-oriented league — if you’re not having success, shouldn’t your team replace you with somebody else who might?

You’d think so. And sure enough, most of the GMs who are remembered poorly fall short of our five-year cutoff, often by a lot. Even guys that stuck around longer than fans might have wanted, such as John Ferguson Jr. in Toronto, Ron Hextall in Pittsburgh, Ned Harkness in Detroit or Peter Chiarelli in Edmonton, didn’t get to the five-year mark. Five years is a lot.

But now and then, for a variety of reasons, a team sticks with a guy well past the point that results would dictate. Those are the guys we’re interested in today, as we count down the 10 worst GMs to get at least five years with the same team.

10. Mike O’Connell, Bruins

Hired: November 2000, taking on the unenviable role of replacing a living legend in Harry Sinden, who’d held the job since 1972.

Fired: March 2006

In between: O’Connell’s Bruins had decent regular-season success, including finishing first in the division twice. But they never won a round, and it’s fair to say it did not end well.

Signature move: Trading Joe Thornton to the Sharks for Wayne Primeau, Brad Stuart and Marco Sturm. It was a confusing deal at the time, amid reports that the Bruins hadn’t even shopped the former No. 1 pick before taking the Sharks’ offer. It got worse when Thornton won the MVP that year. Two decades later, it’s considered one of the worst trades of all time.

Bottom line: You can’t look past the Thornton trade. But O’Connell did set some of the stage for the good years to come, especially by drafting Patrice Bergeron in 2003.

9. Glenn Sather, Rangers

Hired: June 2000

Fired: July 2015

In between: Clocking in at just over 15 years, this is the longest stint we’ll find on our list. And Sather certainly earned some runway, having built a Hall of Fame resume at his previous stop with the Oilers. That’s where he’s alleged to have uttered the fateful quote about how if he had the Rangers’ payroll, “I’d never lose a game.”

He did end up in New York, and he did lose games. Quite a few, actually. The Rangers failed to make the playoffs in any of Sather’s pre-lockout seasons, which ironically were the ones where he could outspend everyone. They improved over the years to come, especially over Sather’s last two seasons, in which they won a Presidents’ Trophy and went to the final. But it’s those early years that many fans remember.

Signature move: Signing every bad UFA contract you can remember from that era.

Bottom line: Sather is the classic case of a GM who seemed to get the blame when things were bad, and not much of the credit when they were good. I wonder if we’d remember his time in New York the same way if it weren’t for that infamous quote.

8. Max McNab, Capitals

Hired: December 1975

Fired: November 1981

In between: A whole lot of losing. Which was to be expected, given that McNab took over an expansion team that had one full season under its belt, that being arguably the worst any team has ever had. Still, in five seasons at the helm, McNab’s Caps never finished with more than 70 points.

Signature move: He had some solid draft success, as you might expect given all the Capitals’ high picks. His best was picking future 700-goal man Mike Gartner fourth overall in 1979.

Bottom line: McNab’s miserable record means he really has to be on this list, but he had absolutely nothing to work with. Of note, he’s one of the few guys on this list who got another crack at a GM job, running the Devils for the four years before Lou Lamoriello arrived.

7.5. Ron Francis, Kraken

Hired: The Kraken named Francis the first GM in franchise history in July 2019.

Fired Promoted: He was moved up to president this past April.

Wait, time out: Should Francis count? I’m not sure that he should. In a technical sense, he was the Kraken’s GM for almost six years. But he couldn’t do much for the first two years, so it feels like we should really start the clock at the expansion draft. That was in 2021, meaning Francis was only a GM of a team with actual players for a little less than four years.

In between: That expansion draft was widely panned, not just because of who the Kraken took but because they failed to make any significant moves around the draft or their cap space. The Golden Knights had built a Cup contender by doing that in 2018, although it’s fair to say other GMs weren’t going to fall for the same trick again. But still … nothing? Combined with doing very little in terms of big moves in his subsequent years, it’s not an impressive track record for such a crucial role in a new market.

Signature move: Was there one? I guess you could say getting two firsts from Tampa for Yanni Gourde.

Bottom line: In the end, I don’t think he counts. But he deserves a mention.

7. Michael Barnett, Coyotes

Hired: August 2001, when he followed longtime client Wayne Gretzky to Arizona as a rookie GM

Fired: April 2007

In between: The Coyotes made the playoffs in Barnett’s first year, winning one game before being knocked aside by the Sharks. That was it for the postseason, as the team dropped to just 67 points by Barnett’s last year. That said, it would be fair to mention that anyone running the Coyotes during this time period had the deck stacked against them.

Signature move: Sending a young Danny Briere to the Sabres at the 2003 deadline.

Bottom line: Let’s face it, Barnett was in Arizona because of Gretzky, and Gretzky was there to sell tickets, and none of it really worked.

6. Doug MacLean, Blue Jackets and Scott Howson, Blue Jackets (tie)

Wait, two guys? Yeah, I didn’t feel like picking on one team with multiple entries. Say what you will about the Blue Jackets, but they love their long-serving GMs. Not counting interim guys, they’ve only had four in franchise history, and that includes Don Waddell.

Anyway, MacLean was the Blue Jackets’ first GM, lasting from February 1998 to April 2007. Howson was next up, from June 2007 to February 2013.

In between: Between them, MacLean and Howson produced one playoff appearance and zero playoff wins. Hey, if it ain’t broke …

In fairness, remember that back then, expansion teams were given virtually nothing to work with. But MacLean didn’t build much, and Howson’s attempts to shove the franchise into relevancy did not work.

Signature move: For MacLean, drafting Rick Nash. For Howson, trading away Rick Nash.

Bottom line: MacLean’s record was worse, although in theory, he had less to work with. Howson did what he could under the circumstances, but may best be remembered for getting a third-place vote as GM of the Year despite being fired a few weeks into the season.

5. Gerry McNamara, Maple Leafs

Hired: October 1981

Fired: February 1988

In between: “GM the GM” built the 1980s Maple Leafs, a team noted for all the success they had. But of course, McNamara was working for Harold Ballard, quite possibly the worst owner in all of pro sports, so he had no chance. Ballard was the one forcing some of McNamara’s most unpopular moves, like trading Darryl Sittler to the Flyers.

Signature move: Managing the team into the league basement in time to draft Wendel Clark No. 1 in 1985.

Bottom line: McNamara didn’t make as many moves as you’d think, basically letting the Leafs drift into a ditch over nearly a decade while his owner counted money and kicked puppies. That said … the Ed Olczyk trade was an underrated banger.

4. Rejean Houle, Canadiens

Hired: October 1995, despite having no front office experience, after Canadiens president Ronald Corey had decided to clean house just a few days into the season.

Fired: November 2000

In between: Yes, Houle just gets in under the wire, clocking in at five years and a month. He had more on-ice success than most of the names on this list, making the playoffs in each of his first three years and even winning a round in 1998. Of course, he also took over a team that was just two years removed from a Cup, so maybe expectations should have been high.

But none of that really matters, because Houle will always be remembered as the GM who traded away arguably the greatest goalie of all time for a handful of magic beans just a few weeks into the job. There was more to that story than just a GM making a bad move — a lot more – but it seemed bad at the time and isn’t looking any better three decades later.

Signature move: The Patrick Roy trade. But Houle pulled off another poorly received blockbuster a year later, sending captain Pierre Turgeon to St. Louis for Shayne Corson.

Bottom line: I’ll be honest, I remember Houle as the guy from the Roy trade, and was surprised to find out that he stuck around this long.

3. Kevyn Adams, Sabres

Hired: June 2020

Fired: Apparently never.

In between: No playoff appearances, little in the way of hope, lots of fan unrest, and the occasional article like this one.

Signature move: Definitely the Jack Eichel trade, and everything that led up to it.

Bottom line: It’s always dangerous to put somebody on a list like this when they’re still building out their body of work. Maybe this looks bad in a year or two. Let’s just say that right now, I’m not getting that vibe.

Jim Benning was the Vancouver Canucks GM from May 2014 to December 2021. (Bruce Bennett / Getty Images)

2. Jim Benning, Canucks

Hired: May 2014

Fired: December 2021

In between: The Canucks made the playoffs in Benning’s first year, with a roster still mostly built by former GM Mike Gillis. They made it again in the 24-team bubble year. In the other five years, they finished under .500.

Signature move: His best and arguably biggest move was trading for J.T. Miller. But in general, the Benning era was known for disappointing drafts and the constant promise that the team didn’t need to rebuild because they were almost there. They were not.

Bottom line: Every Canucks fan right now is going “Wait, Benning wasn’t first?” But then they remembered the one name we haven’t mentioned yet …

1. Mike Milbury, Islanders

Hired: December 1995

Fired: June 2006

In between: Hoo boy.

Look, the one thing you can say about Mike Milbury as a GM: He was not afraid to take a big swing. I do a lot of complaining about timid GMs who are scared of sticking their necks out, so I guess I have to give credit where it’s due — Milbury was not that guy. He made plenty of big moves.

The problem is that those moves rarely worked. And some of them were downright awful. So were his teams, which missed the playoffs in seven of his 10 seasons and never won a round.

Signature move: Do you go with trading a young Roberto Luongo? Drafting Rick DiPietro No. 1? Trading Jason Spezza and Zdeno Chara for Alexei Yashin? The Yashin contract? Trevor Linden? Bryan Berard? Ziggy Palffy? The list goes on. And on. And on …

Bottom line: For Islanders fans, the Milbury era might be the ultimate example of that curse about living in interesting times.

Honorable mentions

Kevin Lowe in Edmonton. Phil Esposito in Tampa Bay. Pierre Dorion in Ottawa. Chuck Fletcher in Minnesota. Don Waddell in Atlanta. And maybe Garth Snow in New York, although he turned out to be pretty good for a backup goalie.