Who was the worst NHL GM to keep his job for five years or 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, like 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 every 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 ten worst GMs to get at least five years with the same team.

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NHL weekend rankings: Naming and shaming the (many) fake .500 teams

If you’re a sports fan, you know what “.500” means. In general, it means you’re average. Mediocre. Just OK. And specifically, it means you’ve won as many games as you’ve lost.

The exception: The NHL. Since 1999, the league has given out points for losing, which is dumb but we’ve been over that. In the NHL, we rank teams based on their points percentage, and because of those loser points, you can have a percentage north of .500 even if you’ve lost more than you’ve won.

Most years, it’s annoying. This year, with the loser point being well and truly out of control, it’s messing up the standings even more than usual. So this week, let’s take a look at five teams that are fake. 500 – which is to say, they’re sitting at .500 or better even though they’ve lost more games than they’ve won. We’ll name and shame those teams here, and rank them from least to most fake.

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Six Patrick Roy-inspired Oilers trades for a goalie that get increasingly demented

Thirty years ago today, there was a very good team with one crucial flaw.

They had an excellent roster, one that included two of the very best centers of their era. The forward depth was good. They had a decent blueline, one anchored by one of the better young offensive defensemen in the league. They had a good young coach. But the flaw was in goal – they had some decent goalies, but nobody who could be The Guy,  the sort of stud who could steal a playoff series or two on the long road to a championship.

Stop me if any of this sounds familiar, Oiler fans.

You know how the story ends. Our team is the 1995-96 Colorado Avalanche, and tomorrow marks the thirty-year anniversary of the biggest transaction in franchise history. On December 6, 1995, the Avalanche acquired Patrick Roy from the Canadiens in a five-player trade, and the rest was history. They won the Stanley Cup that very year, followed not long after by another. Joe Sakic and Peter Forsberg went to the Hall of Fame with multiple rings. And it all happened because Colorado’s front office recognized a problem, and took the biggest swing possible to fix it.

Could this year’s Oilers do the same?

The short answer: No, of course not.

We all know why. There’s a salary cap now. Trading is too hard, especially during the season. The price would be too high. Great players are almost never traded these days. And there’s also the not-very-small detail that Roy had basically walked out on his team a few days earlier, forcing Montreal to make a lopsided deal they wouldn’t otherwise have made. No elite goalies are doing that these days.

OK, sure. This year’s Oilers can’t take a big swing. It’s impossible to land a Roy-sized talent, or even anything close, even if it would be the last piece of a Stanley Cup puzzle. We have to be realistic, and we all know that when the Oilers eventually make their move, it will look a lot more like the 2024 Avs than the 1995 version – which is to say, they’ll try to find a Mackenzie Blackwood or Scott Wedgewood, then hope for the best. Or maybe they won’t do anything at all, and just roll the dice on yet another Stuart Skinner playoff run. But a blockbuster? Never going to happen.

Fine. But what if it did?

Today, on the eve of the anniversary of the Patrick Roy trade, let’s indulge in a little but of make-believe. Let’s pretend we live in an alternate NHL world where a team that was one star goalie away from a championship would actually, you know, go get a star goalie.

Which goalies could be the Oilers’ Patrick Roy? I have six suggestions. None of them are remotely realistic in today’s NHL. This is just a little Friday fun, a thought experiments to take you into the weekend. We'll go from the most to the least plausible.

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Don't set your mascot on fire: One reason to say "no thanks" to all 32 NHL teams

 I tried to be nice.

I really did. Last week, I wrote a whole long piece in which I offered thanks to all 32 NHL teams. It was pure positivity, nothing but puppies and rainbows. Was it out of character? Maybe, but we’re allowed to try new things. And I was trying something very new: Going a whole article without complaining.

And as I should have known would happen, a whole bunch of you responded with: Cool, now flip the script and do the negative version.

Fine. You win. Here’s one reason to say “no thanks” to every team. See if I ever try to be nice again.

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NHL weekend rankings: Early offseason lessons, plus the Wild, Oilers and Sharks

It’s December, which means it’s not too early anymore.

At least, for some things. For example, if a team is struggling to hit .500 at this point, it’s not just a case of a slump or a run of bad luck. That team is bad. There’s still time for them to get good again, absolutely. But right now? There’s no more pointing at the calendar and pretending everything’s OK.

I’m not as convinced that it’s not too early to pass judgement on the offseason. But we’re doing it anyways, so here we go…

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