The postseason -- which is so, so close now -- is more than anything a way to make new memories, ones fans will hold onto for the rest of their lives. But the postseason is also something else: It is a way to try to erase old memories that aren’t so pleasant.
Of the 18 legitimate contenders for a postseason spot, 10 of them -- the Dodgers, D-backs, Giants, Cubs, Phillies, Yankees, Red Sox, Rangers, Royals and Astros -- have won World Series this century. That means there are eight who have not. All eight of those teams have gotten close, or at least gotten close enough to have their hearts broken. Right now, the memories of those losses, and that pain, are still fresh in the minds of their fans. But there’s nothing like a World Series title to turn those frowns, forever, upside down.
Here's a look at the roughest postseason memory, from a century in which they have not won a World Series, for each of those eight contending teams. I apologize in advance to the fans who have to relive these dark times from their past. (Teams listed in alphabetical order.)
Blue Jays
Series that still stings: 2015 ALCS vs. Royals
Blue Jays fans certainly have a lot of postseason pain to choose from: They’ve lost seven playoff games in a row, after all. But no team since those back-to-back champs in the early ’90s ever captured the hearts of Toronto fans like the stacked teams of a decade ago, led by José Bautista, Edwin Encarnación and Josh Donaldson. They reached the ALCS in both 2015 and ’16, but that 2015 loss to the Royals in six games definitely still sticks in the craw the most. The Jays were fighting to stave off elimination in Game 6, and after falling behind, they tied it in the eighth on a dramatic two-run homer from Bautista. But in the bottom of the eighth, Eric Hosmer lined a base hit down the right-field line and Lorenzo Cain scored all the way from first to take the lead. The Jays put runners on first and third with no out in the ninth, but then went down 1-2-3 after that, leaving pinch-runner Dalton Pompey stranded at third. A year later, they’d fall to Cleveland in the ALCS in five games, and they haven’t won a postseason series since, having been swept in the Wild Card round in 2020, ’22 and ’23.
Brewers
Series that still stings: 2018 NLCS vs. Dodgers
The 2025 Brewers may be the best team this franchise has ever had, but it’s strange how many seem to think they came out of nowhere: This team has won the division two straight years and made the playoffs seven of the last eight years. In 2018, the Brewers won Game 6 of the NLCS against the Dodgers, putting them one win away from their first World Series since 1982, and they even took a 1-0 lead in front of a deafening crowd at Miller Park in Game 7. But Cody Bellinger responded with a two-run homer in the second, Yasiel Puig hit a three-run shot in the sixth and Clayton Kershaw, three days after winning Game 5, came in to close it out to end the Brewers’ hopes.
Guardians
Series that still stings: 2016 World Series vs. Cubs
What more can be said about this one? In an alternate universe, Rajai Davis’ game-tying homer in the eighth inning of Game 7 is an all-time classic homer, up there with Joe Carter and Kirk Gibson and so many others. Instead, it ends up a footnote to the even more historic events that would happen a couple of innings (and a legendary rain delay) later. Guardians fans will forever feel like this one got away. And for good reason.
Mariners
Series that still stings: 2001 ALCS vs. Yankees
This 116-win team is the best Mariners team of all time. It is also one of the greatest baseball teams of all time … and almost certainly the greatest one never to even reach the World Series. This team was almost absurdly fun, with Edgar Martinez and John Olerud and Mike Cameron and a 38-year-old Jamie Moyer and Bret Boone racking up 141 RBIs and, of course, Ichiro Suzuki taking the whole sport by storm in his rookie year. (And remember: This was the year after A-Rod left.) This was supposed to be the team, which made the five-game blitzing the Yankees gave them in this series all the more inexplicable. It would be 21 years until the Mariners sniffed the postseason again, and that ended with a three-game Division Series sweep at the hands of the rival Astros.
Mets
Series that still stings: 2006 NLCS vs. Cardinals
Lord knows the image of Carlos Beltrán taking that third strike off Adam Wainwright is burnt into the brains of every Mets fan who ever saw it. That 2006 team felt special at the time, tying the Yankees for the most wins in MLB (97), nine more than the next-best NL team (Padres, 88 wins). The Mets have had some October thrills since then, such as their surprisingly deep runs in 2015 and 2024, but you can argue that 2006 was the last time they felt like legitimate World Series favorites.
Padres
Series that still stings: 2024 NLDS vs. Dodgers
It has only been a year, but many people have still forgotten how, heading into this series, it really did feel like the Padres’ year. They had played fantastic down the stretch, swept the Braves in the Wild Card Series, beaten the Dodgers in the 2022 NLDS, and they just looked, all told, like the more complete team. They also had a 2-1 lead heading into Game 4 in front of a levitating Petco Park crowd with the Dodgers putting forth a bullpen game … only to lose 8-0. When they went back to Dodger Stadium, they managed only two hits in a 2-0 loss to the eventual world champions. The Padres haven’t been to the World Series since 1998, and one suspects, if they’re going to do so this year, they’ll have to go through the Dodgers to get back there.
Reds
Series that still stings: 2012 NLDS vs. Giants
How long has it been since the Reds won a postseason series? Well, Elly De La Cruz was seven years away from being born. (It was 1995. Frank Viola was on that team.) Poor Joey Votto never won a single playoff series. The closest he came -- and he was so, so close -- was in 2012, when the Reds jumped out to a 2-0 series lead against the Giants, with both wins coming in San Francisco no less. Three heartbreakers would follow, all in Cincinnati: An extra-inning Game 3 loss, Tim Lincecum vexing the Reds in Game 4 and a six-run Giants fifth inning to clinch the series in Game 5. The Giants won the World Series that year. Votto, who had a .500 OBP in that NLDS, would only play in three postseason games the rest of his career. The Reds would lose all three.
Tigers
Series that still stings: 2013 ALCS vs. Red Sox
The Tigers have made the World Series twice this century, but they were both over with quickly: Down in five to the Cardinals in 2006 and swept by the Giants in 2012. Their two ALCS losses, to the Red Sox in 2013 and the Rangers in 2011, were probably more painful. That 2013 loss looks worse now, considering that was peak Miguel Cabrera, with Justin Verlander and Max Scherzer in the rotation. But if you want to pick one of those World Series flops to be worse … I won’t argue with you.