It was raining. Not a downpour, just a persistent, annoying drizzle that threatened to wash away 108 years of North Side misery. If you're a baseball fan, you know exactly where you were on November 2, 2016. Maybe you were pacing your living room in Lakeview, or maybe you were watching through your fingers in a dive bar in Des Moines.
The last time Cubs won the World Series, the world felt like it was shifting on its axis.
People talk about "breaking the curse" like it was some magical event involving a goat and a cloud of glitter. It wasn't. It was a gritty, terrifying, 8-7 extra-inning victory against the Cleveland Indians (now the Guardians) that almost didn't happen. Honestly, the Cubs tried their hardest to blow it. Rajai Davis hit a home run off Aroldis Chapman in the 8th inning that sounded like a funeral bell for the city of Chicago.
The Inning That Changed Everything
Most people remember the win, but they forget the 17-minute rain delay.
That delay saved them.
Jason Heyward, who was struggling at the plate, dragged the team into a cramped weight room during the weather break. He didn't give some "Win one for the Gipper" speech. He basically told them they were the best team in the league and to quit moping. It worked. Ben Zobrist—the guy who always seemed to be in the right place at the right time—hit a double in the 10th to drive in the go-ahead run.
Miguel Montero added an insurance run, which turned out to be vital because Cleveland didn't go quietly.
When Mike Montgomery came in to get the final out, a slow roller to Kris Bryant, everyone held their breath. Bryant was smiling before he even threw the ball to Anthony Rizzo. You could see it on the replay. A genuine, "we actually did it" grin.
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Why the 2016 Roster Was Different
The last time Cubs won the World Series, it wasn't a fluke. Theo Epstein had spent years tearing that team down to the studs.
Think back to 2012. They lost 101 games. It was pathetic. But they were stockpiling guys like Javier Báez and Kyle Schwarber. Schwarber is a legend for that series alone. He tore his ACL and LCL in the third game of the regular season. He wasn't even supposed to be walking, let alone hitting. Yet, there he was, batting .412 in the World Series as a designated hitter. He looked like he’d just walked off a construction site and decided to destroy world-class pitching for fun.
The rotation was also a freak of nature. Jon Lester brought the veteran "I've been here before" energy. Kyle Hendricks, "The Professor," looked like he was doing his taxes while pitching in the most high-pressure game of his life. Jake Arrieta was still in his prime, looking absolutely untouchable when his sinker was working.
The Emotional Weight of 108 Years
You can't talk about the last time Cubs won the World Series without mentioning the people who didn't see it.
The morning after the win, the brick walls of Wrigley Field became a massive chalkboard. Thousands of people wrote the names of their fathers, grandmothers, and great-uncles who lived and died without ever seeing a trophy. It was heavy. It was beautiful.
That’s the part the statistics don’t show.
For a century, being a Cubs fan was a personality trait built on failure. "Wait 'til next year" wasn't just a slogan; it was a way of life. When that final out hit Rizzo’s glove, that entire identity evaporated. Suddenly, they weren't the "Loveable Losers" anymore. They were just champions.
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Tactical Decisions and Near Disasters
Joe Maddon got a lot of heat for how he managed that game. Still does.
Taking out Kyle Hendricks early in Game 7 is a move that fans still debate at bars on Clark Street. Hendricks was cruising. Then Maddon brought in Lester, who was pitching on short rest, and David Ross (who was retiring after the game). A wild pitch scored two runs for Cleveland. It felt like the "Cubs being the Cubs" again.
But Ross redeemed himself. He hit a home run in his final professional game. Talk about a storybook ending. How many guys get to go out like that?
The bullpen was gassed. Aroldis Chapman had been used so much in Games 5 and 6 that he didn't have his triple-digit fastball when he needed it most. He was pitching on fumes and heart. When Davis took him deep, it felt like the 1945 goat was personally laughing at every person in a blue jersey.
The Aftermath and the "What If"
If you want to understand the last time Cubs won the World Series, you have to look at what happened next.
Everyone thought it was the start of a dynasty.
With Bryant, Rizzo, Báez, and Schwarber all under 30, it seemed like they’d win three or four. But baseball is a cruel sport. Injuries happened. Guys lost their swing. The front office made some trades that didn't age well. By 2021, the "Core" was traded away in a fire sale that broke hearts all over again.
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Rizzo went to the Yankees. Bryant to the Rockies (eventually). Báez to the Tigers.
It makes that 2016 trophy even more precious. It wasn't the start of an era; it was a lightning strike. A perfect, chaotic, rain-soaked moment where everything aligned for a group of guys who refused to let a century of history dictate their future.
Specific Stats You Might Have Forgotten
- The Cubs were down 3 games to 1. Only a handful of teams have ever come back from that in the World Series.
- Game 7 lasted 4 hours and 28 minutes, not including the rain delay.
- Dexter Fowler hit a lead-off home run in Game 7. First time that ever happened in a Game 7.
- The 2016 Cubs won 103 games in the regular season, the most for the franchise since 1910.
Actionable Takeaways for Fans and Historians
If you’re looking to relive the magic or research the era, don't just watch the highlights. The real story is in the nuances.
Watch the full Game 7 rain delay footage. Seeing the players’ faces during those 17 minutes tells you more than any box score. You can see the shift from "we're doomed" to "we've got this."
Read "The Cubs Way" by Tom Verducci. If you want the deep architectural details of how Epstein built the team, this is the bible. It explains the scouting reports and the psychological profiles they used to pick players who wouldn't buckle under the pressure of the "curse."
Visit the Wrigley Field walls. Even years later, the energy around the stadium is different. The "curse" is gone, but the history is baked into the bricks.
Study the 3-1 comeback. Analyze Game 5. People forget that Game 5 was a 3-2 nail-biter. If the Cubs don't win that at home, there is no Game 7.
The last time Cubs won the World Series, it proved that no streak is permanent. It took 108 years, a rain delay, and a group of young stars who didn't care about ghosts. Whether you're a die-hard fan or a casual observer, that night remains the gold standard for high-stakes drama in American sports.
Next time you find yourself near Addison and Clark, look at the championship banner. It represents more than a trophy. It represents the night the most famous drought in sports finally ended in a puddle of rain and a pile of happy players on a Cleveland infield.