The Lightning are a lock to go deep, and other lessons from the prediction contest

And then there were two. And soon, just one winner.

No, this isn’t a Stanley Cup preview post that accidentally ran a few days early. It’s an update on the annual playoff prediction contest, which is already over for almost all of you. We’ll get to that in a bit.

But first, a refresher. This is the contest that seems simple, because it’s only one question: Name as many or as few playoff teams as you’d like based on how many games they’ll win, in order from most to least. That’s it. We even give you the benefit of the doubt on ties, because we want you to succeed. But you don’t. Did I mention that you’re not good at this? Because you’re not.

You can find this year’s contest post here, and if you entered, you can find your answer by heading to the comment section of that post and using the dropdown to select “my comments”. But you probably don’t want to do that, because spoiler alert, there’s a roughly 99.8% chance that you’re out of the running.

Let’s get into what happened, and why you’re bad at this.

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Which bad Canadian ads should I make Other Sean watch?

It’s almost time for one of my favorite annual traditions: The exchange of terrible playoff commercials between a Canadian (me) and an American (other Sean).

But which ads should I force him to watch? The field is crowded this year, so I’m asking for your help. Please choose up to three ads from the list below, or post your own nominations in the comments.

But first, a quick word about Lay It On The Line, which is at the top of pretty much every Canadian’s “please no more I’m begging you” list this year. I didn’t put that one on the list, for two reasons. First, I think it’s actually a good ad that’s just been way, way, way (way way way) overplayed; somebody seeing it for the first time wouldn’t necessarily think it was all that bad. And second, I’m led to believe that a lot of Americans have already seen it, including Other Sean. I’ll make it’s included in the actual post one way or another, but I don’t think it’s a great candidate to be one of the official three Bad Ads.

With that in mind, let me know what you think with the form below (which I may update with new ads as they're suggested):

Auston Matthews and Connor Hellebuyck lead the 2025 NHL playoffs all-bust team

We’re well into the conference finals, having now witnessed over a month’s worth of playoff performances. For some fans, now would be the time to celebrate the best of the best, and spend some time admiring the players who’ve elevated their games when it matters most.

For the other 99% of us, there’s this column. It’s playoff disappointment time.

As always, some ground rules™:

• We’re building a 21-man roster, with 12 forwards, six defensemen and three goalies, because we’ll need that extra guy. Beyond that, positions don’t matter. We’ll also have a coach and GM, because the guys in suits deserve some scrutiny too.
• There’s a maximum of three spots per team.
• Every playoff team must be represented at least once.

And yes, that last rule applies to the teams that are still playing, which opens the door to that fun situation where I call somebody a bust and then they score four goals that night. I’m willing to take that risk, because it’s the playoffs, and it’s all about courage.

As with any great team, we build from the net out…

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Which NHL team should win the 2025 Conned Smythe for worst trade with a contender?

With the conference finals well underway and the Stanley Cup final looming, it’s time to focus in on the top candidates for the game’s most important playoff award: The Conned Smythe.

Yes, that’s “Conned” and not “Conn”. We all know about the Conn Smythe, given to the playoff MVP. But that’s an individual award, and as we’re constantly being reminded, hockey is a team game. And the Conned Smythe is a team award. Specifically, the award that goes to the team that had the biggest impact on the playoffs by making the worst trade with a contending team.

This is a fake award I invented a few years ago, and it’s been retroactively awarded for every year of the cap era. The 2023 Golden Knights gave us a ton of strong candidates, and last year’s field was competitive. You might be wondering if this year’s contenders are just going to be a rehash of last year’s list, given three of the four finalists are the same. But with plenty of big moves in the year since, some shifting dynamics among those teams, and a “no repeat winners” rule that I basically just made up to be nice to Sabres fans, there’s actually plenty of turnover in this year’s candidates.

As always, these need to be player trades – no trading of future draft picks who turned into guys, and no waivers or free agency. We’ll count down ten candidate teams, from weakest to strongest, based on how the field looks right now.

And yes, you think you know where this is going. But it’s going to be a tougher call than you think.

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Playing "What if?" with 6 key Maple Leaf decisions from the Brendan Shanahan era

It’s over. The Brendan Shanahan era is all but done, Mitch Marner is all but gone, and big changes seem imminent in Toronto. The Maple Leafs, or at least this version of them, have failed.

Did it have to be this way?

That’s the big question these days. To hear some tell it, yes, this was the inevitable outcome all along, because playing in a big market like Toronto is just too much to ask from the toughest athletes in the world. Others would tell you that the Shanaplan was doomed from the very start, because it was built around the wrong core. And some would just shake their heads and mutter something about being cursed.

Then there’s the side that says no, it didn’t have to be this way – that there were multiple branching paths along the road that made a different destination possible. That’s the premise of today’s piece, as we look at a half-dozen key checkpoints in recent Maple Leafs history, and wonder what would have happened if a different decision was made.

Our starting point here is 2018 or so. The Leafs have already drafted Auston Matthews, Mitch Marner and William Nylander. They’ve made a surprise playoff run in their first year together, then nearly knocked off the established Bruins in year two. Brendan Shanahan has a plan, and it’s working. While there’s a long way to go, the future is as bright as it’s ever been.

And then… well, we know what comes next. But what if? We won’t go too deep down the alternate history hole on any of these – if you’re looking for fan fic that ends with the Leafs winning all the Cups, you’ll have to write it yourself – but each is worth exploring. And at the end, I'll even let you tell me the right answer.

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DGB "Leafs Lose" mailbag: Thoughts on Shanahan, Marner, hope, and all those boos

It’s the middle of May, which means that the Toronto Maple Leafs have lost. It took a little longer this time, with this team going deep into the second round, but the ending was the same: An absolutely brutal no-show, fans and media pleading for something to change, and this time we mean it.

Sounds like it’s time for a spring tradition around these parts: The annual “the Leafs lose again” mailbag. Let’s see what was on your mind this time around.

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It's "Leafs Lose" mailbag time

Hey folks...

It's an annual tradition like no other: The Leafs are out, so we're doing a mailbag. Have a question? Want to propose a trade? Just need to vent? Whatever it is, send your questions, comments and rants via email at dgbmailbag@gmail.com.

Thanks,
Sean

Ranking the 16 possible Stanley Cup final matchups, based purely on narratives

Once the first round of playoffs was over, we could say goodbye to eight teams. And more importantly for our purposes today, we could also say goodbye to 48 potential Stanley Cup finals.

Sorry, anyone hoping for Blues vs. Canadiens in a rematch of the 1969 final, or Kings vs. Senators in a re-litigation of the Dion Phaneuf trade. Losing half of our playoff teams means we lose three-quarters of our possible final combinations – thanks, math – bringing us down to a manageable 16. Gosh, that almost feels like the right number for a ranking.

To be clear, we’re going to be going from the worst possible matchup to the best, based purely on narratives and vibes. After all, why was Stars/Avalanche the best and most memorable series of the first round? Because the two teams were super-talented and played close games at a high level? Fool! It was because of Mikko Rantanen, and the power of the revenge game.

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The right and mostly wrong (but maybe right?) of my Oddly Specific Predictions

Every year, just as the regular season is set to begin, I make Oddly Specific predictions for each NHL team. It’s one of my very favorite columns to write each year.

And then in the spring, I have to see if I actually got any right. That’s today’s column, and it is not one of my favorites.

But we have to do it because accountability matters, so here we go. If you’re new to the Oddly Specific prediction game, it’s exactly what it sounds like: A prediction for each team that gets a little too detailed. It’s not enough to say a team will have more points; we need an exact total. Don’t tell us something will happen; give us the specific game. Anyone can predict an Alexander Ovechkin goal; let’s see you plant the flag for Joel Hanley.

That last one, of course, is maybe our most memorable hit – in 2022, I didn’t just predict that defensive defenseman Hanley would finally score his first regular season goal, but also gave you the exact game it happened in. It was pretty amazing. I’ve been chasing that high ever since.

I’ll save you the suspense: This year’s predictions, which you can go back and read here, don’t have any Hanley-level miracle calls. At least… not yet. But we’ll get to that.

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One-way offside? Free range faceoffs? NHL Rules Court is back in session

Welcome to Rules Court, the feature where you send in your proposals for NHL rule changes and three of us vote on them. Convince at least two of us, and your rule is passed.

This is, by my count, the ninth edition of this feature. Over the years, we’ve changed everything from the salary cap to replay review to the playoff format, in some cases multiple times. We’ve also made it so that coaches have walk across the ice to serve bench minors. We’re really doing the lord’s work, is what I’m trying to say.

Today we’re back with seven new suggestions sent in by readers. They’ll be reviewed by Sean, Other Sean and Shayna (aka Almost Sean). Will any get the required YES votes to be passed into the NHL rulebook? Let’s find out…

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Five games that changed the outcome of the 2025 draft lottery

Did you enjoy this year’s draft lottery? I did. I thought the new format for the broadcast, which featured the full draw happening live, was a major improvement. As much as I like to complain about the lottery, and occasionally suggest alternatives that would be way better, we appear to be stuck with what we’ve got. And if so, at least the league kind of nailed the presentation this year.

But while the NHL changed the broadcast, they didn’t change the underlying mechanism. That means they still assigned each team a group of combinations, based on their record. And that means that all those combinations, including the winning ones, were tied to a specific spot in the standings. And that means that shifting the teams that finished in the winning 19th and 23rd spots in the standings would have changed the results.

Which means… yep, we get to go looking for games that changed the lottery results.

This is a gimmick we break out every now and then, if and when the results allow it. Sometimes we get a drawing like last year, where the Sharks won the lottery after being five points worse than any other team. No game can give you a five-point swing, so there was no point looking any deeper. But this year, the lottery gods had a few surprises up their sleeves with those longshot wins for the Islanders and Utah, so we can have some fun with the results.

Well, “fun” might be relative here. Half the point is that this won’t be fun for certain fan bases, who may not realize just how close they came to a potentially franchise-altering draft pick. We’re trying to make you sad, here. It’s kind of our thing.

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Greatest revenge games in sports, from Mikko Rantanen’s Game 7 to Brett Favre to Luka Dončić

We love a good revenge game, don’t we folks?

It’s an irresistible sports trope. A player leaves a team under murky circumstances — maybe against their will or maybe there’s a footprint on their back as they head out the door — then, inevitably, they get to face their former team, and they teach them a lesson. And the lesson is: You done messed up.

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Draft lottery power rankings: Who needs it, who deserves it, who might trade it?

It’s now been ten years since I wrote a column that lives in infamy.

Back then, while working for a site called Grantland, I decided it would be fun to write a power rankings-style column about the upcoming NHL draft lottery. There was a kid named Connor McDavid available that year, so the lottery had huge ramifications for the teams involved. So I wrote the piece, one that built towards the main punchline that any result would be fine as long as the Oilers didn’t win. And everyone had a good laugh.

Then the lottery happened, and nobody was laughing anymore.

It all worked out for the best, he said, in case any Oiler fans were reading, and the lottery power rankings went on to become a tradition. A decade later, it’s time to dig into our annual lists of who needs it, who deserves it, and who Gary Bettman is going to rig it for.

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Suggestions for the hockey gods: Eight ways this latest Leafs collapse could end

The Toronto Maple Leafs are coughing up yet another playoff series they should win. They’ve now lost 13 of the 14 games in the Auston Matthews era in which they’ve had a chance to eliminate an opponent. Five of those games have featured blown leads. Five have come in overtime. There’s been at least one in every year since 2018. And now it’s all happening again, in the same way, to the same group, building to Saturday’s inevitable Game 7 loss.

I know you know all that stuff. I just wanted to make sure any especially sensitive Maple Leaf fans had a chance to click away in horror before we went any further.

You wouldn’t think there’d be many of those fans left. After all, anyone who’s been paying attention over the years should be thoroug

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