If you ask a random person on the street about Chicago Cubs World Series wins, they’ll probably mention a rain delay, a goat, or Bill Murray crying in the stands. It’s the 2016 obsession. People act like the franchise didn't exist before Theo Epstein showed up with a spreadsheet and a dream. But the reality is way weirder. The Cubs were actually the first true dynasty in professional baseball, even if that feels like a lifetime ago. Or several lifetimes.
They’ve won three titles. That’s it. 1907, 1908, and 2016.
It’s a bizarre statistical curve. You have this massive explosion of dominance at the start of the 20th century, followed by a literal century of wandering in the desert, and then a high-octane, modern analytical masterpiece of a season. If you're looking for a consistent winning tradition, you're looking at the wrong team. But if you want to understand how a fan base survives on a diet of "maybe next year" for 108 years, you have to look at the specific DNA of those three championships.
The Forgotten Dynasty: 1907 and 1908
Nobody alive remembers these. We have black-and-white photos of guys in baggy wool uniforms looking miserable, but the 1907 and 1908 squads were terrifying. They were the Golden State Warriors of the Deadball Era.
In 1907, the Cubs didn't just win; they embarrassed the Detroit Tigers. They went 107-45 in the regular season. Think about that. They won over 70% of their games. Ty Cobb was on that Tigers team, and the Cubs pitchers—led by Mordecai "Three Finger" Brown—absolutely neutralized him. Brown is a legend for a reason. He lost parts of two fingers in a farm machinery accident as a kid, which gave his curveball a rotation that modern physics still struggles to explain. He finished the 1907 season with a 1.39 ERA.
The 1907 World Series actually started with a tie. Game 1 went 12 innings and ended 3-3 because of darkness. No stadium lights back then. After that, the Cubs just rattled off four straight wins. It was a sweep in spirit.
Then came 1908. This is the year everyone cited for over a century. It’s the year of "Merkle’s Boner," one of the craziest officiating blunders in sports history. Basically, Fred Merkle of the Giants failed to touch second base during a game-winning hit because fans rushed the field. The Cubs noticed, got the ball (some say it wasn't even the game ball), touched second, and got the force out. The game was declared a tie, the Cubs won the makeup game to take the pennant, and then they crushed the Tigers again in the World Series.
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They were back-to-back champs. At that moment, if you told a Cubs fan they wouldn't see another trophy until their great-great-grandchildren were retirees, they would’ve called you insane.
Why the Gap Was So Long
You can't talk about Chicago Cubs World Series wins without talking about the losing. It defines the wins. Between 1908 and 2016, the Cubs actually made it to the World Series seven times (1910, 1918, 1929, 1932, 1935, 1938, and 1945). They lost every single one.
They lost to the Babe Ruth Yankees. They lost to the Tigers. They lost to the Athletics.
By the time the 1945 series rolled around, the "Curse of the Billy Goat" was born. William Sianis, owner of the Billy Goat Tavern, was allegedly kicked out of Wrigley Field because his pet goat smelled bad. He supposedly said the Cubs would never win again. For a long time, it looked like he was right. The team became a symbol of lovable failure. Even when they had superstars like Ernie Banks, Ron Santo, or Billy Williams, they couldn't get over the hump. 1969 was a collapse for the ages. 1984 was a heartbreaker. 2003... well, we don't talk about Steve Bartman in certain parts of Chicago.
The drought became a cultural touchstone. It wasn't just sports; it was a lesson in the human condition. It was about loyalty when there was no rational reason to be loyal.
2016: The Anatomy of a Breakout
When the 2016 win finally happened, it wasn't luck. It was a cold, calculated teardown and rebuild. Theo Epstein, the man who broke the Red Sox curse, brought his blueprint to Clark and Addison. He drafted Kris Bryant, traded for Anthony Rizzo, and signed Jon Lester.
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The 2016 regular season was a juggernaut performance. They won 103 games. They had the best defense in the history of the game according to several defensive runs saved metrics. But the World Series against the Cleveland Indians (now the Guardians) was a nightmare for the first four games.
The Cubs trailed 3-1.
Statistically, their chances were hovering around 15%. They won Game 5 at Wrigley. Then they went to Cleveland and blew the doors off Game 6 behind an Addison Russell grand slam.
The Greatest Game 7 Ever
If you want to understand the peak of Chicago Cubs World Series wins, you just have to watch Game 7 of 2016. It was a 10-inning epic that felt like a movie script written by someone who tried too hard to be dramatic.
- Dexter Fowler hits a lead-off home run.
- The Cubs build a 6-3 lead.
- Joe Maddon pulls Kyle Hendricks too early (debatable, but fans still argue about it).
- Aroldis Chapman, exhausted from previous games, gives up a two-run homer to Rajai Davis.
- The game goes into a rain delay.
That rain delay saved the franchise. Jason Heyward famously called a players-only meeting in a weight room. He told them they were the best team in the league and to just go play like it. When the tarp came off, Ben Zobrist hit a double that changed the course of Chicago history. When Mike Montgomery got Michael Martinez to hit a slow roller to Kris Bryant for the final out, a century of psychic weight evaporated.
The Cubs won 8-7. It was nearly 1:00 AM in Chicago. People were literally going to cemeteries the next day to leave pennants and "W" flags on their parents' graves. It sounds melodramatic, but that's what happens when a city waits 108 years.
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The Reality of the Modern Cubs
Expectations changed after 2016. Suddenly, just being "competitive" wasn't enough. The core of Bryant, Rizzo, and Baez eventually moved on, and the team entered a new phase.
The Cubs have struggled to replicate that 2016 magic. It turns out that winning a World Series is incredibly hard, and doing it with the weight of a century on your back is almost impossible. The front office has pivoted toward a "sustained success" model, but fans are restless. They don't want to wait until 2124 for the next parade.
Common Misconceptions About Cubs Titles
- "The Cubs have only won once." Nope. As mentioned, the 1907 and 1908 teams were absolute powerhouses. They were arguably better relative to their competition than the 2016 team.
- "The Curse was real." It was a marketing gimmick that got out of hand. The real reason the Cubs didn't win was poor scouting, bad trades (like Lou Brock for Ernie Broglio), and an unwillingness to invest in the farm system for decades.
- "Wrigley Field is the reason they lose." Some people claim the day games or the wind at Wrigley hurt the home team. While the "Wrigley factor" is real for betting lines, it didn't stop them from being a top-tier team in the 30s or the 2010s.
How to Track Cubs Success Moving Forward
If you're following the team's quest for more Chicago Cubs World Series wins, you need to look past the box score. The modern game is won in the pitching lab and the draft room.
- Watch the Farm System: Keep an eye on MLB Pipeline. The Cubs' ability to develop homegrown pitching—something they failed at for most of the 2000s—is the key.
- The Jed Hoyer Strategy: Hoyer (the current President of Baseball Operations) is more conservative than Epstein. He looks for "intelligent spending." This means fewer massive 10-year contracts and more high-value, short-term deals.
- NL Central Volatility: The division is often wide open. The path to the playoffs usually goes through St. Louis or Milwaukee. If the Cubs can't dominate their own division, they have zero chance at a title.
What You Should Do Next
If you want to truly appreciate the history of the Cubs, don't just watch the highlights of the 2016 Game 7. Go look at the 1908 roster. Look at the ERA of their starting rotation. It's mind-bending.
Visit Wrigley Field, but don't just sit in the bleachers and drink. Walk the concourse. Look at the statues. There’s a specific energy there that comes from a century of hoping for the best and expecting the worst.
To keep tabs on the current roster's chances, follow beat writers like Sahadev Sharma or Patrick Mooney. They provide the actual context that the national media misses. Don't fall for the "lovable losers" narrative anymore. That ended in 2016. Now, the Cubs are just another big-market team trying to figure out how to beat the Dodgers and the Braves.
The drought is over, but the pressure to win another one is just starting to build. Honestly, that might be a heavier burden than the curse ever was.