Ask any baseball fan about the Chicago Cubs and they'll probably sigh. For a century, the team was synonymous with "next year." People genuinely believed in ghosts and goats. When you ask when did cubs win the world series, the answer isn't just a date; it's a timeline of a three-peat that took 108 years to finish.
They won it all in 1907. They did it again in 1908. Then, the world changed. Empires fell, the internet was born, and the Cubs just... kept losing. Finally, in 2016, they broke the most famous curse in American sports. It was messy. It was loud. It rained.
The Early Dynasty Nobody Remembers
It’s kinda wild to think about, but the Cubs were the first real dynasty in Major League Baseball. Before the Yankees were even a thing, Chicago was the gold standard. In 1907, they swept the Detroit Tigers. Well, technically it was 4-0-1 because of a tie, but they dominated. Ty Cobb was on that Tigers team and he couldn't do anything against the Cubs' pitching.
Then came 1908. This is the year everyone cited for over a century. If you lived through the 1990s or early 2000s, "1908" was basically a slur in the North Side of Chicago. They beat the Tigers again, four games to one. Mordecai "Three Finger" Brown was the hero. He literally only had three fingers on his throwing hand due to a childhood farm machinery accident, and he used that to create a curveball that defied physics.
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You’d think a team that won back-to-back titles would be set for a while. They were. They stayed competitive for years. They made it to the World Series in 1910, 1918, 1929, 1932, 1935, 1938, and 1945. They just lost every single one of them.
The Billy Goat and the Drought
1945 is where things get weird. This is the "Curse of the Billy Goat." William Sianis, owner of the Lincoln Tavern, tried to bring his pet goat, Murphy, into Wrigley Field for Game 4 of the World Series against the Tigers. The usher said no. Sianis allegedly said, "The Cubs ain't gonna win no more."
They didn't.
For 71 years, they didn't even make it back to the Fall Classic. They had some great players—Ernie Banks, Ron Santo, Billy Williams—but the team was cursed. Or just poorly managed. Depends on who you ask.
2016: The Year the World Actually Ended (For the Curse)
The answer to when did cubs win the world series changed forever on November 2, 2016. Honestly, it was one of the most stressful nights in the history of televised sports. The Cubs were facing the Cleveland Indians (now the Guardians). Both teams had massive championship droughts, but the Cubs’ 108-year gap was the headline.
Cleveland was up 3-1 in the series. Statistically, the Cubs were dead. No team had come back from a 3-1 deficit in the World Series since the 1985 Royals. But they won Game 5 at Wrigley. Then they blew out Cleveland in Game 6.
Game 7 was a fever dream.
Dexter Fowler hit a lead-off home run. The Cubs built a 5-1 lead. It looked like a cakewalk. Then, Rajai Davis hit a two-run homer off Aroldis Chapman in the 8th inning to tie it. The air left every lungs in Chicago. I remember watching it and thinking, "Here we go again. The goat wins."
The Rain Delay that Saved a Franchise
Then it rained.
A 17-minute rain delay happened right before the 10th inning. Jason Heyward, who had struggled all year at the plate, reportedly pulled everyone into a weight room. He told them they were the best team in the league. He told them to forget the 8th inning.
Ben Zobrist hit a double. Miguel Montero drove in another. The Cubs took an 8-6 lead. In the bottom of the 10th, Cleveland scored one, making it 8-7. With a runner on, Mike Montgomery came in to pitch. Michael Martinez hit a soft grounder to Kris Bryant.
Bryant slipped. He actually smiled while he was throwing the ball. He knew he had it.
The ball hit Anthony Rizzo’s glove, and 108 years of frustration evaporated. If you were in Chicago that night, you didn't sleep. The city sounded like a war zone with fireworks. It was a massive, collective exorcism.
Why 2016 Was Different
Theo Epstein is the guy who gets the credit. He’s the executive who broke the "Curse of the Bambino" in Boston in 2004, then moved to Chicago to do it again. He basically tore the team down to the studs. He drafted Kris Bryant, Kyle Schwarber, and Javy Baez. He traded for Anthony Rizzo.
It wasn't luck. It was math.
The 2016 Cubs weren't just "scrappy." They were a juggernaut. They won 103 games in the regular season. They had the best defense in the league by a long shot. They had Jon Lester and Kyle Hendricks at the top of the rotation.
People ask when did cubs win the world series because they want to know about the miracle, but the 2016 win wasn't a miracle. It was a five-year plan that finally hit its peak.
Key Players from the 2016 Championship
- Kris Bryant: The NL MVP who played everywhere.
- Anthony Rizzo: The soul of the team and a gold-glove first baseman.
- Ben Zobrist: The World Series MVP who hit the most important double in Chicago history.
- Kyle Schwarber: A guy who tore his ACL in April and came back in October to hit .412 in the World Series. That shouldn't be humanly possible.
- Jon Lester: The veteran lefty who gave them the "big game" experience they lacked.
Understanding the Context of the Drought
To really grasp the weight of the Cubs winning, you have to look at what happened between 1908 and 2016.
When the Cubs won in 1908, Arizona and New Mexico weren't even states. The Ottoman Empire existed. Radio hadn't been invented for the masses. Most people still got around on horses.
The "Loveable Loser" brand became a defense mechanism. Fans at Wrigley Field became famous for showing up regardless of how bad the team was. It was a social club that happened to have a baseball game in the background. But that culture shifted under Epstein and manager Joe Maddon. They made it okay to expect to win.
Misconceptions About the Cubs Winning
A lot of people think the Cubs have only won once. Nope. As mentioned, they have three titles.
Another common myth is that the "Bartman Incident" in 2003 was a World Series game. It wasn't. That was the National League Championship Series (NLCS). Steve Bartman, a fan who tried to catch a foul ball, became the scapegoat for a collapse that was actually caused by the shortstop booting a double-play ball and the pitching staff falling apart.
Also, many people forget that the Cubs almost won in 1984. They were up 2-0 on the Padres in a best-of-five series and lost three straight. That one hurt just as much as 2003 for many older fans.
The Legacy of the 2016 Team
That team didn't become a dynasty. They didn't win another World Series. By 2021, most of the core players—Rizzo, Bryant, Baez—were traded away.
But it doesn't matter.
In Chicago, those guys are immortals. You can walk into any bar in Lakeview today and see a 2016 championship banner. The answer to when did cubs win the world series is now a source of pride instead of a punchline.
It changed the city's DNA. The desperation is gone. Now, when the Cubs struggle, fans are just regular-annoyed, not "cosmically-cursed" annoyed.
How to Explore Cubs History Today
If you're looking to dive deeper into the lore of the Cubs championships, don't just look at the stats. Do these three things to get the real vibe of the franchise:
- Visit Wrigley Field: It's the second-oldest park in the majors (built in 1914). Even if there's no game, walk around the statue of Ernie Banks and see the ivy. It's a museum that sells hot dogs.
- Watch "The 2016 World Series" Documentary: Major League Baseball produced an official film narrated by Vince Vaughn (a huge Cubs fan). It captures the 17-minute rain delay better than any textbook could.
- Read "The Cubs Way" by Tom Verducci: This is the definitive book on how Theo Epstein built the 2016 team. It’s a masterclass in sports management and psychology.
- Look up the "College of Captains": Research the 1960s era when the Cubs tried to play without a single manager, using a rotating committee instead. It explains why the drought lasted so long—they were genuinely experimental (and often bad).
The story of the Chicago Cubs isn't just about baseball. It's about patience. 108 years is a long time to wait for a party, but by all accounts, the one in 2016 was worth it.