History is a heavy thing. If you grew up in Chicago or anywhere near the North Side, the question of when did the cubs win a world series isn't just a trivia point you look up on a phone while sitting at a bar. It was a generational weight. It was a curse involving a goat. It was a black cat. It was a guy in a turtleneck reaching for a foul ball.
For the longest time, the answer was 1908. That was it. One single year that felt like it belonged to another planet. 1908 was before the Titanic sank. It was before World War I. Teddy Roosevelt was in the White House, for crying out loud.
Then came 2016.
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Everything changed on a rainy November night in Cleveland. If you’re looking for the short answer, the Chicago Cubs have won the World Series three times: 1907, 1908, and 2016. But the gap between those dates—that 108-year desert—is where all the real stories live. Honestly, it’s one of the most statistically improbable stretches in the history of professional sports.
The early glory and the 108-year drought
People forget that in the early 1900s, the Cubs were actually a powerhouse. They weren't the "Lovable Losers" yet. They were a juggernaut. Led by the famous double-play trio of Joe Tinker, Johnny Evers, and Frank Chance—immortalized in that "Baseball's Sad Lexicon" poem—the Cubs dominated.
In 1907, they swept the Detroit Tigers. In 1908, they beat them again, four games to one. At that point, if you told a Cubs fan they wouldn’t see another trophy until their great-grandchildren were retired, they’d have laughed you out of West Side Park.
Then the "Curse of the Billy Goat" happened in 1945. William 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 reportedly declared, "The Cubs ain't gonna win no more."
Whether you believe in curses or just bad management, the Cubs didn't even make it back to the World Series for 71 years after that. They had amazing players. Ernie Banks, "Mr. Cub" himself, hit 512 home runs and never played a single postseason game. Think about that. One of the greatest to ever swing a bat, and he never saw October.
Breaking the wall in 2016
When people ask when did the cubs win a world series, they are almost always talking about 2016. That season was different from the start. Theo Epstein, the guy who broke the curse for the Red Sox, had been building a "tank and rebuild" model in Chicago for years. By 2016, the roster was stacked. Kris Bryant was the MVP. Anthony Rizzo was the soul of the team. Jon Lester brought the veteran grit.
But it’s the Cubs. It couldn't be easy.
They trailed the Cleveland Indians (now the Guardians) three games to one. Nobody comes back from 3-1 in the World Series. Well, almost nobody. They clawed back to force a Game 7.
That Game 7 is widely considered the greatest baseball game ever played. Dexter Fowler hit a lead-off home run. The Cubs built a lead. Then, in the 8th inning, Rajai Davis hit a two-run homer off Aroldis Chapman that literally shook the stadium. I remember watching that and thinking, "Here we go again. The goat is back."
Then came the rain.
A literal act of God. A 17-minute rain delay before the 10th inning gave Jason Heyward a chance to pull the team into a weight room and give a speech that became legendary. Ben Zobrist—the ultimate utility man—hit a double down the left-field line to take the lead. Miguel Montero added insurance.
When Mike Montgomery got Michael Martinez to hit a slow grounder to Kris Bryant, and Bryant’s foot slipped but he still threw it to Rizzo... that was it. 11:47 PM ET. The drought ended.
The weird math of Cubs championships
It’s kind of funny when you look at the raw numbers. Here is the actual breakdown of the years the Cubs took it all home:
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- 1907: Beat Detroit 4-0-1 (yes, there was a tie in Game 1).
- 1908: Beat Detroit 4-1. They were the first team to ever win consecutive World Series.
- 2016: Beat Cleveland 4-3. The greatest comeback in franchise history.
There are some common misconceptions here. Some people think they won in 1945—they didn't, they lost to Detroit in seven games. Others remember the 1969 collapse or the 1984 heartbreak against the Padres and assume there was a trophy in there somewhere. Nope. Just a lot of "wait 'til next year."
The 2016 win wasn't just a sports victory. It was a massive cultural exhale. Estimates say 5 million people showed up for the parade in Chicago. It was one of the largest human gatherings in history. People were writing the names of their deceased parents and grandparents on the brick walls of Wrigley Field in chalk because those relatives had lived and died without ever seeing a win.
What most people get wrong about the drought
A lot of folks think the Cubs were just terrible for 108 years. That’s not true. They had some incredible teams. The 1906 Cubs actually hold the record for the highest winning percentage in MLB history (.763), winning 116 games. But they lost the World Series that year to their crosstown rivals, the White Sox.
The issue wasn't always talent; it was often "the moment."
Take 2003. The Steve Bartman game. People blame that poor guy in the stands for reaching for a ball, but they forget that the Cubs still had a lead, Alex Gonzalez botched a double-play ball right after, and they had a whole Game 7 left to play which they also lost. The narrative of being "cursed" became a self-fulfilling prophecy that put a massive amount of pressure on the players.
Even Joe Maddon, the manager in 2016, talked about "The Burden." He tried to make things light—bringing zoo animals to practice, wearing pajamas on road trips—just to get the players to forget that they were playing for a century of frustrated fans.
Why 1908 and 2016 matter today
Knowing when did the cubs win a world series helps you understand the current state of the MLB. The 2016 win effectively "killed" the identity of the Cubs as the lovable losers. Now, they are expected to spend like a big-market team. They are expected to compete.
The front office today, led by Jed Hoyer, is constantly operating in the shadow of that 2016 peak. Fans are no longer patient. Once you prove you can win, the "lovable" part of "lovable loser" disappears pretty fast.
If you’re a collector or a history buff, 1908 remains the holy grail. Programs and memorabilia from that era are incredibly rare because, frankly, people in 1908 didn't think it was going to be their last win for a century. They didn't preserve things the way we do now.
Actionable steps for fans and historians
If you want to dive deeper into the history of these wins, don't just look at the box scores.
- Visit the Billy Goat Tavern: It’s located under Michigan Avenue in Chicago. It’s a dive bar, but the history is plastered on the walls. It gives you a sense of the superstition that defined the team for decades.
- Read "The Cubs Way": Tom Verducci wrote a fantastic breakdown of how the 2016 team was built. It explains the scouting and the psychological shifts needed to break the streak.
- Check out the Wrigley Field Marquee: If you go to the corner of Clark and Addison, the marquee is the most iconic sign in sports. After a win, they still fly the "W" flag, a tradition that started back when people used to check the flags from the elevated train to see if the team won.
- Watch the Game 7 Documentary: "The 2016 World Series" film produced by MLB is some of the best sports cinematography out there. It captures the tension of the rain delay perfectly.
Understanding the timing of these championships gives you a map of American history. From the dead-ball era of 1908 to the high-tech, analytics-driven era of 2016, the Cubs have been the primary barometer for the soul of baseball. They represent the idea that eventually, no matter how long it takes, the rain stops and the game resumes.