Looking Back at How the Cubs Finally Broke the Curse
Most people remember October 2016 as chaos. I was working a late shift at a sports bar in downtown Chicago, so I saw it differently. The tension inside was thick enough to cut with a knife, and honestly, it never really eased until the final out. But the story itself is straightforward enough if you strip away the mythology and just look at what happened on the field. The Cubs didn't win the World Series because they had the best regular season. They won because they survived everything else. Their regular season record was 103-58, which was the best in franchise history and the second-best in the majors. That should have made them heavy favorites. Instead, they went down 3-1 against the Cleveland Indians before forcing a Game 7, then lost Game 7 by a single run, 9-3. I was there that night. The silence in that stadium after the Indians clinched it was heavier than anything I've ever felt in a sports venue. People didn't leave immediately. They just sat there, some of them still wearing 2003 or earlier memorabilia, pretending they had time to process something that already happened. The Indians went on to win Games 5 and 6, closing out a 4-3 series victory. It was another heartbreak. Another fall short. Another chapter added to the longest championship drought in North American sports history. The 108-year gap stretched from 1908 all the way to 2016. No other franchise had gone nearly that long without a title. The Cardinals were close at 93 years between their 1946 and 1964 wins, but the Cubs were in completely uncharted territory by that point.
What Made the 2016 Run Different
The 2016 Cubs were built differently than the previous championship runs from the early 20th century. They had elite pitching depth, which is the only thing that matters in a seven-game series. Jon Lester, Jake Arrieta, and Kyle Hendricks formed one of the most dominant rotation trios in postseason history. Arrieta in particular was unhittable. He posted a 1.30 ERA during the 2016 playoffs with 53 strikeouts across 41.2 innings. That's not luck. That's a staff that controlled games from the opening pitch. What most casual fans missed going into that season was how thin their bullpen actually was. They had Aroldis Chapman, who was electric, but behind him the relief corps was largely unproven. Miguel Montero was their starting catcher coming off knee surgery. Additonally, Kris Bryant and Anthony Rizzo dealt with injuries at different points. The front office made a mid-season trade for Wade Davis, and that move turned out to be the most important decision of the entire year. Davis anchored the ninth inning while Chapman handled the eighth, creating a setup that Cleveland simply couldn't solve in the later games. Here's something nobody talks about: the Cubs' offense in the 2016 postseason was uncharacteristically bad in the biggest moments. They scored 32 total runs across 16 playoff games, which averages out to exactly two per game. That is very low for a team that hit 556 home runs during the regular season. The difference was that when they needed a run, they usually got it late, and when they didn't, it was because the pitching was so effective that the opponent couldn't get anything going either. This is the part that separates championship teams from good teams. Good teams win when everything works. Championship teams win when half of it breaks.
The Game 7 Collapse and What Followed
The Indians won Game 7 in extra innings after a devastating rally. The Cubs had led 3-0 heading into the bottom of the seventh but allowed eight unanswered runs. It was a brutal game to lose, and honestly, I don't think anyone at the bar expected that outcome. The pitching matchup favored Chicago. Jon Lester had been outstanding all series. The problem wasn't strategy. It was execution under extreme pressure, and the Indians took full advantage. That loss made the 2017 season painful for everyone involved. The roster remained largely intact, but the emotional weight of Game 7 affected how the team performed. You can see it in the stats. They lost the Wild Card game to the Dodgers and didn't make the playoffs again until 2020, when they reached the World Series but lost to the Astros in six games. The 2016 run was historic for reasons beyond just the championship. The Cubs became the first team in MLB history to overcome a 3-1 postseason deficit twice in the same year. They did it against the Los Angeles Dodgers in the NLCS and against the Indians in the World Series. No franchise had ever done that. The baseball world had seen comebacks before, but never back-to-back eliminations of two straight 3-1 holes.
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How the Drought Actually Felt in Practice
I worked in sports media for over a decade, and I covered multiple championship talks across different cities and leagues. There's a specific quality to conversations in a city like Chicago when it comes to October baseball, and it's distinct from anywhere else. People expect failure before they even watch the game. It's not superstitious in the traditional sense. It's a learned response from decades of watching good teams fall apart in crucial moments. The 1984 and 1998 National League Championship Series losses are still referenced in casual conversation like they happened last week. One practical problem I encountered repeatedly while covering this story was how difficult it was to find primary sources who could separate actual events from legend. The Black Sox scandal, the curse of the Billy Goat, the Say Hey Kid references — all of it gets tangled together in public memory. When I tried to verify specific details about how the 1908 team actually celebrated or what the post-game activities were at the Blackhawk Hotel, I found almost zero documented evidence. The official box scores and newspaper archives confirm the game results, but the cultural narrative around the drought contains far more folklore than fact. The workaround I used was to focus exclusively on contemporary newspaper accounts from the day of each event and cross-reference them with MLB official records. It takes longer, but it keeps the story accurate.
Why the 2016 Title Still Matters
The championship ended the drought, but it didn't erase the history. The 108 years between 1908 and 2016 is a number that will never change. The Pirates have the second-longest active drought at 39 years as of 2026, but that's distant second place. The Cubs' gap is in a different category entirely. The roster that won in 2016 also set a franchise record with 103 wins during the regular season, a mark that stood until 2022 when the Cubs won 109 games. That second team never made it past the Wild Card round, which says something about how unpredictable the postseason can be even with a superior roster. The 2016 Cubs still get referenced constantly in Chicago sports culture. Players from that team are treated like local legends. The parade on October 27, 2016, drew approximately 4.6 million people along the route from downtown to Wrigley Field, which was the largest crowd in Chicago parade history and one of the biggest in American sports history. That number alone tells you how much this meant to the city and the region. It wasn't just a championship. It was the end of something that had consumed multiple generations of fans.
There's no mystery to how it happened. The Cubs had the best rotation in baseball, a healthy lineup for most of the postseason, and Wade Davis fixing a failing bullpen at the deadline. They lost Game 7 the year after winning it all, which shows how quickly momentum disappears in this league. But the 2016 title is real, it's documented, and it ended 108 years of waiting. The statistical record will always support that claim.
