If you walk around the North Side of Chicago today, the "W" flags flying from brownstone porches feel like a natural part of the landscape. But for over a century, that wasn't the case. People spent their entire lives—literally birth to death—asking the same question: have Cubs won World Series titles in the modern era? For 108 years, the answer was a painful, soul-crushing "not since 1908." It wasn't just a losing streak; it was a cultural identity built on the "Lovable Losers" moniker, a goat curse, and a black cat. Then came 2016.
The short answer is yes. The Chicago Cubs have won the World Series three times in their long, storied history. They went back-to-back in 1907 and 1908, then waited longer than any professional sports franchise in North American history to do it again in 2016.
That 2016 win didn't just break a drought. It broke a city. In a good way.
The Ancient History: 1907 and 1908
Most people forget that at the turn of the 20th century, the Cubs were actually a powerhouse. This wasn't a team of destiny; it was a juggernaut. We are talking about the era of "Tinker to Evers to Chance," the legendary double-play trio that eventually made it into the Hall of Fame.
In 1907, they absolutely steamrolled the Detroit Tigers. It was barely a contest. They followed that up in 1908 by beating the Tigers again. At that point, if you had told a Cubs fan in 1908 that they wouldn't see another trophy until their great-great-grandchildren were adults, they would have laughed you out of West Side Park.
Back then, the ball was "dead," the players wore wool in the summer, and the concept of a "night game" was sci-fi nonsense. The Cubs were the kings of baseball. And then, the faucet just... turned off.
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The Curse of the Great Drought
You can't talk about whether the Cubs have won a World Series without talking about why they didn't for over a century. This is where the lore gets weird. Most sports fans know about the Curse of the Billy Goat. In 1945, Billy Sianis, owner of the Billy Goat Tavern, tried to bring his pet goat, Murphy, into Wrigley Field for Game 4 of the World Series. They kicked him out because the goat smelled. Sianis allegedly declared, "The Cubs ain't gonna win no more."
They didn't. For a long time.
It sounds silly now, but when you look at the 1969 collapse or the 1984 NLCS, you start to wonder. Then 2003 happened. The Steve Bartman incident. A fan reached for a foul ball, the Cubs melted down, and the Florida Marlins marched on to the World Series. Honestly, being a Cubs fan was less about baseball and more about waiting for the next creative way to lose.
The Turning Point: Theo Epstein and the Rebuild
The drought didn't end by accident or magic. It ended because Theo Epstein, the guy who broke the "Curse of the Bambino" for the Boston Red Sox, moved to Chicago in 2011. He didn't promise a win. He promised a "foundation."
He traded away fan favorites. He endured 100-loss seasons. He drafted Kris Bryant, Kyle Schwarber, and Javier Báez. He traded for Anthony Rizzo. By 2015, the Cubs were scary. By 2016, they were the best team in baseball.
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The 2016 World Series: How it Finally Happened
The 2016 World Series against the Cleveland Indians (now the Guardians) was, without exaggeration, one of the greatest sporting events in human history. The Cubs were down 3 games to 1. Statistically, they were dead. No team had come back from that deficit in the World Series since 1985.
But they forced a Game 7.
Game 7 was a fever dream. Dexter Fowler hit a lead-off home run. The Cubs built a lead. Then, Rajai Davis hit a two-run homer off Aroldis Chapman in the 8th inning to tie it. The world stopped. Cubs fans everywhere felt that familiar "here we go again" dread.
Then it rained.
A brief rain delay before the 10th inning allowed Jason Heyward to call a players-only meeting in a weight room. He told them how good they were. He told them to forget the past. When the tarp came off, the Cubs scored two runs. Mike Montgomery came in to get the final out, a slow roller to Kris Bryant, who slipped on the wet grass but still fired it to Rizzo.
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The Cubs won. 108 years of waiting, evaporated in a muddy infield in Cleveland.
Why the Cubs Win Still Matters Today
When people ask "have Cubs won World Series" games recently, they are usually looking for the 2016 stats, but the impact goes deeper. The 2016 victory changed the DNA of the franchise. They are no longer the "Lovable Losers." They are a high-revenue, big-market team that is expected to compete every year.
Since 2016, the team has gone through a massive transition. The "Core"—Rizzo, Bryant, Báez—are all gone now. But the 2016 trophy sits in the Wrigley Field archives as proof that the impossible is actually possible.
Realities of Modern Success
- The Cubs have won three titles total (1907, 1908, 2016).
- They have appeared in 11 World Series.
- The 2016 parade was one of the largest gatherings of humans in recorded history (estimated 5 million people).
What to Watch for Next
The current Cubs are in a "retool" phase under Craig Counsell. If you are following the team today, the focus isn't on breaking a curse anymore. It's about building a consistent winner that doesn't require a century-long wait between rings.
If you want to dive deeper into this history, you should look into the specific box scores of the 1908 season. It was actually more dramatic than 2016 in some ways, involving the famous "Merkle’s Boner" incident where a baserunning error by the Giants allowed the Cubs to sneak into the postseason.
Next Steps for Fans and Researchers:
- Check the Stat Sheets: Look up the 2016 Game 7 box score. It is a masterpiece of tactical baseball and high-stress pitching changes.
- Visit Wrigley: If you can, go to the corner of Clark and Addison. The vibes have changed since 2016, but the history is etched into the bricks.
- Watch "The Last Smile": Seek out documentaries on the 2016 run. The footage of the rain delay meeting is legendary for a reason.
- Monitor the Farm System: Keep an eye on the Cubs' current prospect rankings. The 2016 win was built on home-grown talent, and the front office is trying to replicate that blueprint right now.
- Study the 1908 Rulebook: Understanding how the Cubs won their second title helps explain why the game evolved the way it did, especially regarding "protested" games.