Introducing a new NHL award presented to the team with the worst playoff performance

We like to make up awards around here. Over the years, we've introduced the Carson (for best sophomore season), the Bourque (for best final season), and of course the Conned Smythe (for making the trade that decided a championship). Is it kind of dumb? Sure, but no dumber than the Mark Messier Leadership Award, so off we go.
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This time around, I want to introduce a team award, which will be presented to the NHL team that has the worst and most painful playoff performance in any given year.
In theory, that would mean a first-round exit, preferably in as few games as possible. But it's not just about whoever had the shortest run because not all sweeps are created equal. We're looking past the cold, hard numbers here and instead trying to find the true pain. And often, that means getting a team's hopes up before crushing them. In theory, you could even win a round or two before crashing and burning in such spectacular fashion that you never want to speak of it again.
Expectations matter. Opponents matter. And of course, there's plenty of room for artistic impression. We can even use the benefit of hindsight to find the especially painful special circumstances. The point is that anyone can lose, and 15 teams do every year. But which losses really leave a mark? Which ones brutalize a fan base, scarring them for generations?
This sounds fun.
But first, we need an actual trophy for this thing. And for once, we don't even have to invent one. Did you know that the NHL used to have something called the O'Brien Trophy, which was awarded to the Stanley Cup Final loser? Not to be confused with the NBA's Larry O'Brien Trophy, it's one of the NHL's old awards that's now defunct, and for good reason, because hockey culture says you don't celebrate losing. But since that's what we're doing here, it's a perfect fit. Crack open the vault and dust off the O'Brien Trophy, because it's our new award for each postseason's biggest loser.
We'll go back and retroactively hand out the trophy for each year of the cap era, starting way back in the good old days …
Candidates: In an upset-heavy year, we saw the Stars post the league's second-best record, only to get knocked out in five by the Avalanche, while the Predators had the best season in their young franchise history, only to go out in five to the Sharks. Meanwhile, the 100-point Rangers were swept by the Devils. And while the Canadiens were big underdogs against Carolina, they had a 2-0 series lead only to collapse after losing Game 3 in overtime, then had to watch the Hurricanes win the Stanley Cup.
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But the winner is: We start with an easy one. It's the Red Wings, who put together one of the best regular seasons in history with 58 wins and 124 points, only to lose in the first round to the eighth-seeded Oilers. Manny Legace was never seen in Detroit again.
Candidates: Atlanta was the only team swept in the first round, but it was the most successful playoff run in Thrashers history, so we'll skip that. The Stars fought back from down 3-1 to Vancouver only to lose Game 7 on home ice. And the Wild only scored six goals in a five-game loss to the Ducks. Hey, at least it was better than the 2003 conference final.
But the winner is: Remember how the 2006 Predators ran off the best season they'd ever had, only to lose to the Sharks in five? They did it again in 2007, despite going all in to get Peter Forsberg at the deadline.
Candidates: A year after going to the final, the Senators were swept out of round one by the Penguins. The Capitals lost a Game 7 on home ice in overtime.
But the winner is: Let's go with a team that won a round. The Canadiens were the top seed in the Eastern Conference, but needed seven games to get past the Bruins and then got smoked by the Flyers in round two, with rookie Carey Price getting lit up. To make matters worse, the Flyers' leading scorer in the series was R.J. Umberger, whose nine points in five games represented 45 percent of his playoff production over his 11-year career.
Candidates: The Canadiens, Blue Jackets and Blues were all swept in round one, while the Rangers blew a 3-1 series lead against the Capitals.
But the winner is: This one's a close call. The obvious pick would be the Sharks, who won the Presidents' Trophy with 117 points but then lost to the Ducks in six in the opening round. But then you have the Devils, who blew a late lead at home in Game 7 against the Hurricanes in one of the most stunning sequences in memory. It's tough, but in hindsight, we can pinpoint this year as the one that truly started the whole 'San Jose as playoff chokers' narrative, so we'll give the nod to the Sharks.
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Candidates: Man, this is a tough one, because two losses stand out head-and-shoulders over the others. The first is the Capitals, coming off a 121-point season, losing to a red-hot Jaroslav Halak and the Canadiens in round one. In any other year, that's a slam dunk. But we also have the Bruins blowing a 3-0 series lead against the Flyers, becoming just the third team in history to that point to do that.
But the winner is: I think I have to go with the Capitals here. The Bruins fall just short for two reasons. First, their loss came in round two, meaning they at least won a round. And unlike the powerhouse Caps, the Bruins weren't very good, finishing fake .500 on the year. Mix in that hindsight tells us they'd recover just fine in 2011, and I don't think they can be the pick.
Candidates: For what I assume will be the only time in this exercise, it's tempting to go with the team that lost in the Stanley Cup Final, as the Canucks' dream season came crashing down after they'd staked a 2-0 series lead. The Coyotes put up 99 points, only to get swept. And in hindsight, the Sabres blowing a late series lead to lose to the Flyers was the start of The Drought.
But the winner is: I'm going to go with the Canadiens, who lost three agonizing OT games after building a 2-0 series lead against Boston, lost Game 7 in OT (after tying it on a dramatic late goal), and then watched their hated rivals march all the way to their first Cup win in almost 40 years, knowing they could have prevented it all.
Candidates: The Panthers had the Devils down 3-2 and were on the verge of their first series win since 1996, then lost twice in overtime. The Bruins lost to the Caps in Game 7 overtime, while the up-and-coming Hawks were knocked out in round one by the Coyotes.
But the winner is: One year after falling one game short in the final, the Canucks repeated as Presidents' Trophy champs but then bit the shed against the Kings in a five-game opening round loss.
Candidates: The favored Canadiens lost a nasty series to Ottawa in five. The Ducks were upset by the Wings in seven. The once-mighty Canucks were swept aside by the Sharks. And the powerhouse Penguins were a disappointment despite winning two rounds, getting swept by the Bruins in the conference final despite acquiring Jarome Iginla.
But the winner is: Come on.
Candidates: The 101-point Lightning got swept, but you know what, we don't even have to pretend there's any debate to be had.
But the winner is: The Sharks, who blew a 3-0 series lead to the Kings and lost in seven, leaving Joe Thornton looking like this and their reputation as the biggest chokers of the era intact. A few years ago, I ranked this as the most painful Game 7 loss in NHL history.
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Candidates: The Wings blew a 3-2 series lead against Tampa. The Wild won a round, then were swept aside with ease by the Hawks in the second round.
But the winner is: The Jets finally brought playoff hockey back to Winnipeg for the first time in almost two decades, nearly melting eardrums in the process. Then they got swept by the Ducks.
Candidates: The Panthers faced the Islanders in a series in which one team was guaranteed to end a decades-long playoff drought, and lost in six. The Kings got smoked by the Sharks, while the Wings lost in five to the Lightning in what remains their most recent playoff appearance, nine seasons later.
But the winner is: It has to be the Ducks, who were the Pacific's top seed but lost to the Predators in seven. It was the fourth year in a row their season ended in a Game 7, and this one spelled the end of the Bruce Boudreau era.
Candidates: The Wild went out in five easy games to the Blues, meaning they had one more win than the Flames, who were swept by the Ducks. Meanwhile, Alex Ovechkin and the Capitals lost to the Penguins in the second round for the (checks notes) 38th season in a row.
But the winner is: After putting up 109 points to finish first in the West and reestablish themselves as Cup favorites, the Blackhawks were stunningly swept by the eighth-seeded Predators.
Candidates: The Ducks were swept by the Sharks in round one, while the Wild went out in five against the favored Jets.
But the winner is: The Kings, who were swept in round one by the Golden Knights. Who loses to an expansion team, we all laughed, before taking a big sip of water and watching the rest of that year's playoffs.
Candidates: The Flames were the West's top seed but then lost in five to the Avs, which in any other year would have made them a strong contender. The Penguins were swept by the Islanders. And the Leafs lost to the Bruins in seven for the second straight year. Sure hope that doesn't become a thing for this good young team.
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But the winner is: Another easy one, as the Lightning tied the NHL record for wins in a season with 62 and then got swept by the Columbus Blue Jackets, a result that made so little sense that I'm convinced to this day that none of our brains have ever actually tried to process it.
Candidates: We'll count the qualifying round as the playoffs here, even though the league never really got around to clarifying that whole thing. The Rangers were the only team to be swept in that round, while the Leafs blew it against the Blue Jackets. Meanwhile the Blues went in as the West favorite, then lost in round one to the Canucks.
But the winner is: You could make the case that there shouldn't even be a winner here, since the whole bubble playoff setup was so weird that it barely counts as a real postseason. Still, it would have to come down to a pair of qualifying round upsets, with the Penguins losing to the Canadiens or the Oilers losing to the Hawks. I'll invoke hindsight here — we know the Oilers eventually figured it out, while the Penguins have been adrift ever since.
Candidates: The Blues and Oilers were both swept, while the Panthers had sand kicked in their faces by the big brother Lightning. The Hurricanes had the third-best record in the league, but went out meekly in five games in round two.
But the winner is: Come on, part two.
Candidates: The Leafs lost in seven again, and their playoff failures were well and truly A Thing. The Predators got swept. And it's tempting to go with the Panthers, who came off a 122-point season and won a round but then were swept by the Lightning. Two reasons they can't win: First, the series win was their first since 1996, so the season at least felt like some sort of success. And second, we now know that management didn't buy that 'good enough' talk, and immediately embarked on what may go down as one of the great offseasons of all time.
But the winner is: The Wild had 113 points to set a franchise record, then lost in the first round like always.
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Candidates: The Jets were the only team not to even make it to a sixth game, while the Avalanche somehow managed to lose to the Kraken in seven.
But the winner is: This pretty much has to be the Bruins, who racked up arguably the greatest regular season ever to the tune of 135 points and then went up 3-1 in their series against the Panthers before seeing it all blow up in spectacular fashion. Hindsight gets interesting here, because on the one hand, we now know that those 92-point Panthers were a sleeping giant. But we also know that the Bruins were about to plummet, making this loss even more painful.
Candidates: The Leafs lost to the Bruins yet again, and vowed they'd only passively run it back one more time and that was it, and they mean it this time. The Caps got swept and four other teams lost in five in an opening round that was kind of bad. And the Predators lost to the Canucks in six even though by the end of the series, you were starting in goal for Vancouver.
But the winner is: I think this one goes to the Jets, who earned home ice against the Avs but then lost in five when Vezina winner Connor Hellebuyck turned into a pumpkin.
Candidates: The Lightning got smoked by the Panthers, the Blues were a second away from beating the Jets, and the Leafs Leafed again. The Avalanche lost to Mikko Rantanen, who you may have heard once played for them. And you could even make a case for the Stars despite them winning two rounds, since they still couldn't get over the conference final hurdle and their coach got fired after driving the team bus over the franchise goalie.
But the winner is: Maybe it's recency bias, but it feels like there are lots of great candidates for the 2025 trophy. But I think the pick here has to be the Kings, who not only lost to the Oilers for the fourth year in a row despite finally having home ice, but basically handed them the pivotal game with one of the worst coach's challenges ever. The loss plunged the team into crisis and cost Rob Blake his job. Other than that, it went great.
And that's as far as we can go for now. Oddsmakers are already projecting a tight race for 2026, when the Kings lose to the Oilers in three and the Maple Leafs lose to Mitch Marner in seven. No, not his new team — just him.
If you're keeping score at home, we covered 20 years and had 15 different teams take home the trophy. Five teams had multiple wins: Toronto, Los Angeles, Montreal, San Jose and Winnipeg. Hey, look at that, we finally found a playoff trophy that Canadian teams can compete for.
(Top photo of the Kings and Oilers shaking hands: Perry Nelson / Imagn Images)

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