If you grew up a baseball fan, the Chicago Cubs were basically the gold standard for "lovable losers." It’s a harsh label, honestly. But when a team goes over a century without a trophy, people start talking about goats and black cats like they’re legitimate scientific variables. The story of the Cubs in World Series play isn't just a list of wins and losses; it’s a weird, psychological study of a city and its relationship with a sport that seemed determined to break its heart.
The 2016 win changed everything, obviously. But to understand why that rain delay in Cleveland felt like a life-or-death situation, you have to look at the massive gap between the early dominance of the early 1900s and the decades of "wait until next year."
The Dynasty Nobody Remembers
Everyone focuses on the drought. They forget that the Chicago Cubs were the first real dynasty of the 20th century. Between 1906 and 1910, this team was a juggernaut. We're talking about a squad that won 116 games in 1906—a record that stood alone until the 2001 Mariners tied it. They actually lost the World Series that year to their crosstown rivals, the White Sox, which is a detail that still stings for old-school North Side fans.
Then came 1907 and 1908. Back-to-back titles.
Mordecai "Three Finger" Brown was a monster on the mound. He’s a guy who lost parts of his fingers in a farm machinery accident as a kid, which ended up giving his curveball this devastating, unnatural break. He dominated the Detroit Tigers and Ty Cobb. In 1908, the Cubs didn't just win; they looked like they would never lose again.
Then, the silence started.
It’s not like they disappeared. They made it back in 1910, 1918, 1929, 1932, 1935, 1938, and 1945. Seven appearances in 35 years is actually incredible. Most teams would kill for that. But the Cubs in World Series games during this era were defined by being the "bridesmaid." They ran into some of the greatest teams ever assembled. In 1932, they had the misfortune of playing the Yankees when Babe Ruth allegedly "called his shot" at Wrigley Field. Whether he actually pointed to the center-field bleachers or just at the Cubs dugout is still debated by historians like Leigh Montville, but the result was the same: the Cubs got swept.
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Why 1945 Was the Real Turning Point
Most people know about the Billy Goat Curse. William Sianis, owner of the Lincoln Tavern, tried to bring his pet goat, Murphy, into Game 4 of the 1945 World Series against the Tigers. He was kicked out because the goat smelled. Allegedly, he said, "The Cubs ain't gonna win no more."
People laugh it off now. But for the next 71 years, the Cubs didn't even reach the World Series.
The 1945 series itself was weird. Because of World War II travel restrictions, the first three games were played in Detroit and the last four in Chicago. Usually, it's a 2-3-2 format. The Cubs were actually up 2 games to 1. They blew it. They lost Game 7 at home, and that was the last time a World Series game was played at Clark and Addison until the Obama administration.
The Mental Grind of 2016
When Theo Epstein took over as President of Baseball Operations in late 2011, he didn't care about goats. He cared about "The Process." He basically tore the team down to the studs. He traded away veterans for prospects like Kyle Hendricks and Anthony Rizzo. He drafted Kris Bryant. He spent big on Jon Lester.
By 2016, the Cubs weren't just good. They were the best team in baseball by a mile. They won 103 games. But being the favorite is its own kind of pressure when you have a century of failure on your shoulders.
The 2016 World Series against the Cleveland Indians (now the Guardians) was objectively one of the best ever played. It had everything. The Cubs fell behind 3 games to 1. Statistically, their chances of winning were hovering around 15%. No team had come back from 3-1 by winning Games 6 and 7 on the road since the 1979 Pirates.
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Game 7 was a fever dream.
Dexter Fowler leads off with a home run. The Cubs are cruising. Then, Joe Maddon pulls Kyle Hendricks early. Jon Lester comes in and gives up runs on a wild pitch. Then, the moment every Cubs fan felt the "curse" returning: Rajai Davis hitting a two-run, game-tying homer off Aroldis Chapman in the 8th inning.
The sound in that stadium was deafening. Chapman was gassed. The Cubs looked defeated.
And then? It rained.
That 17-minute rain delay is arguably the most famous weather event in sports history. Jason Heyward famously called a players-only meeting in a weight room. He basically told them, "We're the best team in the world for a reason. Forget the last eight innings."
Ben Zobrist—who was the MVP for a reason—hit the double in the 10th. Miguel Montero drove in another. Even then, the Cubs almost blew it in the bottom of the 10th. When Mike Montgomery came in to face Michael Martinez, every person in Chicago was holding their breath. A slow grounder to Bryant, a slip on the grass, a throw to Rizzo.
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The drought was over.
Misconceptions About the Cubs and the World Series
A big mistake people make is thinking the Cubs were always bad. They weren't. They were often very good, just profoundly unlucky or poorly managed in big moments.
Another misconception: Wrigley Field was always this "friendly confines" paradise. In reality, the lack of lights until 1988 was a huge competitive disadvantage. The Cubs had to play way more day games than anyone else, which messed with their sleep cycles and recovery, especially during the hot Chicago summers. Some baseball historians, like Bill James, have argued that the "Wrigley factor" contributed to the team fading in September and October for decades.
Also, let's talk about Steve Bartman. Poor guy. 2003 wasn't even the World Series; it was the NLCS. But because the Cubs in World Series history was so sparse, that moment got lumped into the "World Series curse" narrative. The truth is, the Cubs gave up eight runs in that inning. Alex Gonzalez booted a double-play ball that would have ended the threat. Bartman didn't lose that game; the Cubs did.
What This Means for Baseball Now
The 2016 victory didn't just help Cubs fans; it changed the way front offices build teams. The "Cubs Model" of extreme rebuilding followed by aggressive spending became the blueprint for the Astros, the Braves, and the Orioles.
But it also removed the "mystique." The Cubs are now just another big-market team with a massive payroll and high expectations. They aren't the underdog anymore. When they missed the playoffs or went out early in 2017 and 2018, the reaction wasn't "Oh, the curse." It was "Why aren't they hitting?"
Actionable Insights for Fans and Historians
If you want to really understand the history of this team beyond the surface-level highlights, you should look at these specific areas:
- Study the 1906-1910 Stats: Look at the pitching staff. The Deadball Era stats are insane. Ed Reulbach and Three Finger Brown put up numbers that seem like video game glitches today.
- The 1945 Box Scores: Notice how many players were just returning from the war. The quality of play was erratic, which explains the high-scoring, messy games.
- The 2016 Game 7 Rewatch: Watch the body language of the players during the rain delay. You can find raw footage that shows the shift in energy.
- Visit the Neighborhood: If you go to Wrigley, don't just stay in the park. Look at the flags on the roofs nearby. The history of the "W" flag is a tradition that dates back to the 1930s as a way to tell commuters on the "L" train if the team won without them having to buy a newspaper.
The Cubs are no longer the team of "someday." They are a team of "remember when." For a fan base that spent a century looking forward with dread, having a history to look back on with pride is a weird, new feeling.