If you walk into a bar in downtown Cleveland and ask, "Have the Indians won the World Series?" you're going to get a complicated look. It's a "yes, but" kind of answer. Technically, the franchise known for over a century as the Cleveland Indians has reached the mountaintop. They’ve hoisted the trophy. They’ve had the parades.
But there’s a catch.
Most of the people who were alive to see the last one happen aren't with us anymore. We are talking about a drought so long it feels less like a sports statistic and more like a piece of ancient folklore.
The Short Answer: Yes, They Have
To be perfectly blunt: Yes, the Cleveland Indians won the World Series twice. They did it in 1920 and 1948.
Since then? Nothing but heartbreak, rain delays, and "what ifs." Following the 2021 season, the team officially rebranded as the Cleveland Guardians, meaning the "Indians" era ended with exactly two titles in the trophy case.
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If you're a fan of the team now, you're currently enduring the longest active championship drought in Major League Baseball. Since the Chicago Cubs finally broke their curse in 2016—ironically by beating Cleveland in a soul-crushing Game 7—the title of "MLB’s Longest Wait" belongs solely to the corner of Carnegie and Ontario.
1920: The First Taste of Glory
The 1920 World Series was basically a movie script. It was the first time the franchise—then led by player-manager Tris Speaker—reached the Fall Classic. They were facing the Brooklyn Robins (who we now know as the Dodgers).
This series was weird. It was a best-of-nine format, which MLB experimented with for a few years. Cleveland won it five games to two.
But honestly, the win was overshadowed by tragedy. Earlier that season, Cleveland’s star shortstop Ray Chapman was hit in the head by a pitch and died. He remains the only player in MLB history to die from an injury sustained during a game. The team played the rest of the year with "Chappie" on their minds, and winning that first title was as much about him as it was about the rings.
Why 1920 Was Historically Ridiculous
Game 5 of that series is still talked about in hushed tones by baseball nerds. Three things happened in that single game that had never happened before:
- Elmer Smith hit the first grand slam in World Series history.
- Jim Bagby Sr. hit the first home run by a pitcher in a World Series.
- Bill Wambsganss recorded the only unassisted triple play in World Series history.
Imagine seeing all of that in one afternoon. You’d think the sport had peaked right then and there.
1948: The Last Time Cleveland Ruled the World
If 1920 was the "tragedy and triumph" year, 1948 was the "powerhouse" year. This team was loaded. You had Lou Boudreau (another player-manager, because apparently Cleveland loved that), the legendary Bob Feller, and Larry Doby, who had just broken the American League color barrier the year before.
They faced the Boston Braves. Not the Atlanta Braves—the Boston Braves. That’s how long ago this was.
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Cleveland won the series 4-2. The clincher happened in Boston, with a young pitcher named Gene Bearden coming out of the bullpen to shut the door.
At the time, nobody thought it would be the last one for 75+ years. They had Satchel Paige on the roster, for crying out loud. They were the kings of the American League. They were inevitable.
Then the "curse" (or just really bad luck) started.
The Near Misses: Why the Question Is So Painful
The reason people still ask "Have the Indians won the World Series?" isn't because they're a bad franchise. It's because they've been so close so many times. Since 1948, the team has made it back to the World Series four times.
Each one was a different flavor of agony.
1954: The 111-Win Heartbreak
The 1954 Indians were statistically one of the best teams to ever step onto a diamond. They won 111 games in a 154-game season. They were heavy favorites against the New York Giants.
Then Willie Mays made "The Catch."
Cleveland got swept. Four games to zero. The best team in franchise history didn't win a single game in October.
1995 & 1997: The 90s Juggernaut
If you grew up in the 90s, you remember the "Jake." Sold-out crowds for 455 consecutive games. A lineup featuring Jim Thome, Manny Ramirez, Albert Belle, and Kenny Lofton. In '95, they ran into a dominant Atlanta Braves pitching staff (Maddux, Glavine, Smoltz). They lost in six.
In '97, they were two outs away from winning it all against the Florida Marlins. They had the lead in the 9th inning of Game 7. Then Jose Mesa blew the save, and the Marlins won it in the 11th. That one still hurts. People in Cleveland still won't say Mesa's name in certain neighborhoods.
2016: The Rain Delay
This was the big one. Cleveland vs. Chicago. Two historic droughts. Something had to give.
Cleveland was up 3-1 in the series. They let the Cubs crawl back to tie it. Then came Game 7. Rajai Davis hit one of the most famous home runs in history to tie the game in the 8th. The stadium literally shook.
Then the rain came.
A 17-minute rain delay before the 10th inning killed Cleveland's momentum. The Cubs scored two in the 10th. Cleveland scored one. They lost 8-7. It is widely considered the greatest baseball game ever played, but for Indians fans, it’s a horror movie.
Does the Name Change Affect the History?
When the team became the Cleveland Guardians in 2022, some fans worried the history would be erased. It isn't. MLB considers the Guardians the same continuous franchise that began in 1901.
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All the records, the two World Series trophies, and the retired numbers stayed. The "Indians" won the World Series, and by extension, the franchise has won it.
Honestly, a lot of locals feel like the name change might be the only way to shake the bad vibes. If you can't win as the Indians for seven decades, maybe the "Guardians of Traffic" (the statues on the Hope Memorial Bridge that inspired the new name) can provide some better luck.
The Current State of the Search
Right now, the team is in a weird spot. They have one of the best modern managers in Stephen Vogt (taking over after the legendary Terry Francona) and a perennial MVP candidate in José Ramírez. They consistently overachieve with one of the lowest payrolls in baseball.
But until they win that third ring, the ghost of 1948 is going to keep haunting Progressive Field.
Actionable Takeaways for Fans and Historians
If you’re looking to dive deeper into why this team is so significant despite the long wait, here is how to actually engage with the history:
- Visit the Heritage Park: If you're ever in Cleveland for a game, go to the center-field area of Progressive Field. They have a detailed history of the 1920 and 1948 teams, including plaques for Feller and Speaker.
- Watch 'The Last Duel': Seek out footage of the 1948 series. Seeing Satchel Paige and Larry Doby in those old-school wool uniforms gives you a real sense of how much the game has changed—and how long this wait has truly been.
- Track the "Active Drought" List: Keep an eye on the Texas Rangers and Arizona Diamondbacks. As other teams win their first titles, the pressure on Cleveland only intensifies.
- Understand the Rebrand: Don't let the name change confuse your trivia. The "Indians" name is the one on the 1920 and 1948 banners, but the Guardians are the ones tasked with ending the drought.
The answer to "Have the Indians won the World Series?" is a firm yes. They just haven't done it since Harry Truman was in the White House and a gallon of gas cost 16 cents.