The Milwaukee Brewers finally did it. After 57 years of grinding it out, they officially snatched their first Commissioner’s Trophy in the 2026 World Series. It was a guaranteed first-time winner this year, and the Brewers took down the Tampa Bay Rays in five games, sealing the deal with a 4-1 victory in Game 5.
This isn’t just a win for Milwaukee, it’s a statement about the changing tide in MLB. The Brewers are the fourth franchise in the past decade to claim their first title, joining the Houston Astros (who have two now, 2017 and 2022), the Washington Nationals (2019), and the Texas Rangers (2023). Plus, we all remember when the Chicago Cubs snapped their ridiculous 108-year drought back in 2016. That’s a lot of long-suffering fanbases finally getting their moment. But here’s the kicker: with the Brewers off the list, only four MLB teams are still stuck in title purgatory, waiting for their chance in the sun.
Three Tries, Three Failures: The Rays’ Unwanted Record
And topping that list, unfortunately, are the Tampa Bay Rays. They now hold the lamentable status of being the team with the most World Series appearances without ever winning one. Think about that: they’ve been to the Fall Classic three times, just as many times as the other three teams on this list combined. Ouch.
For their first decade, the Rays were pretty much a punchline, finishing dead last in nine out of ten seasons in the powerhouse AL East. Things shifted big time in 2008, when an analytics-focused overhaul led by Andrew Friedman, now the Dodgers’ president of baseball operations, finally paid off. They made a World Series run, but ultimately fell to the Philadelphia Phillies in five games. Fast forward to the COVID-altered 2020 season, and who was waiting for them in the World Series? Friedman’s Dodgers, who beat them in six games. And now, in 2026, they lost again, this time in five games. It’s a brutal run for a franchise that’s been consistently competitive but just can’t get over that final hump.
Longest Waits and Rocky Roads
While the Rays might have the most World Series appearances without a ring, it’s the San Diego Padres who have been around the longest without ever breaking through. They came into existence as an expansion team in 1969, the very same year as the Brewers (who, fun fact, started as the Seattle Pilots before moving). The Padres’ first shot at glory came in 1984, led by a young Tony Gwynn. They lost to a dominant Detroit Tigers team in five games. Then, in 1998, with Gwynn still on board, they made it back, only to get swept by the New York Yankees dynasty in a series that wasn’t even close. The Padres have been competitive since 2020, spending big money on name-brand talent, but that’s only resulted in one NLCS appearance in 2022. This past season, they beat the Chicago Cubs in the wild-card round, only to lose 3-1 to, you guessed it, the Brewers in the NLDS.
Then there are the Colorado Rockies, who have been consistently struggling since their first season in 1993, holding the third-worst winning percentage in MLB. They just extended their streak of last-place finishes in the NL West to five seasons, following a three-season stretch of finishing fourth. They’ve never even won a division title! The Rockies have made the playoffs five times in 34 years, most recently in 2018, when they got swept out of the NLDS by none other than the Brewers. It seems the Brewers were making a habit of ending other teams’ dreams even before their own came true.
So, the Brewers finally did it in 2026, but the question now looms large over 2027: which one of these four will be the next to break through and finally get their moment in the sun? Every at-bat, every pitch, every single game this season for these teams will carry that weight, that hope, and that burning desire to get off this infamous list. The clock is ticking, and the baseball world is absolutely glued to see who’s next.
This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.
Originally reported by Yahoo Sports.
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