Rain. It always comes back to the rain. If you were watching Game 7 in 2016, you remember exactly where you were when the sky opened up over Cleveland. It felt like a sick joke. After 108 years of waiting, the Chicago Cubs had finally clawed back from a 3-1 deficit, only to see Rajai Davis blast a game-tying home run off Aroldis Chapman in the eighth. The momentum hadn't just shifted; it had evaporated. Most fans sitting in those damp seats at Progressive Field—and millions more huddled around TVs in Wrigleyville—assumed the "Curse of the Billy Goat" had simply found a new, cruel way to manifest.
But then the clouds broke.
Honestly, that 17-minute rain delay changed the course of baseball history. It gave Jason Heyward the chance to gather the team in a cramped weight room for a speech that has since become the stuff of legend. He didn't talk about X’s and O’s. He told them they were the best team in the league. He reminded them they played for each other. When play resumed in the tenth inning, the Cubs didn't look like a cursed franchise. They looked like a juggernaut. Ben Zobrist’s double down the left-field line drove in the go-ahead run, and suddenly, the weight of a century was lifting. When Kris Bryant fielded that final ground ball, slipping slightly on the wet grass but grinning before he even threw to first, it wasn't just a win. It was an exorcism.
The Blueprint: How Theo Epstein Rebuilt a Loser
You can't talk about how the Cubs won the World Series without talking about the "The Plan." When Theo Epstein arrived in Chicago in 2011, he didn't promise a quick fix. He promised a total teardown. It was ugly for a while. The 2012 Cubs lost 101 games. They were bad. Really bad. But while the big-league club was floundering, the front office was hoarding high-ceiling hitters.
Epstein and Jed Hoyer had a specific philosophy: draft "big-batch" hitters because pitchers are too volatile and prone to injury. They took Kris Bryant. They took Kyle Schwarber. They traded for Anthony Rizzo, who became the heartbeat of the clubhouse. They snagged Addison Russell and Javier Báez. By 2015, the "Core" was ready.
But a bunch of kids can't win a ring alone. The 2016 season happened because the front office finally went all-in on pitching. They backed up the truck for Jon Lester, a guy who knew how to win in October. They traded top prospect Gleyber Torres for Aroldis Chapman in a move that was controversial at the time—and honestly still is—because it was a pure "win now" gamble. They also brought in Joe Maddon, a manager who used "Keep It Sexy" as a mantra and brought zoo animals to spring training to keep the guys loose. It was a weird, perfect alchemy of analytics and vibes.
The 103-Win Regular Season
People forget how dominant that 2016 team was before the playoffs even started. They finished 103-58. Their run differential was a staggering +252. Kyle Hendricks, a guy who throws about 88 mph on a good day, led the league in ERA. Jake Arrieta was still a force. Dexter Fowler, the "you go, we go" catalyst at the top of the lineup, had the best season of his career.
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It felt different. For the first time in generations, Cubs fans weren't waiting for the other shoe to drop. Or at least, they were trying not to. The regular season was a victory lap, but the postseason... that was a different animal entirely.
Facing the Giants and the "Even Year" Magic
The road through the National League wasn't exactly a cakewalk. First, they had to deal with the San Francisco Giants in the NLDS. Remember, the Giants had won the World Series in 2010, 2012, and 2014. "Even Year Magic" was a real thing people feared.
In Game 4 of that series, the Cubs were down 5-2 in the ninth inning. It looked like the series was headed back to Chicago for a terrifying Game 5. Then, the Cubs exploded. They put up four runs in the top of the ninth. It was the largest blown lead in a clinching game in postseason history. That was the moment many fans realized this wasn't the "Loveable Losers" of the past. These guys were relentless.
Then came the Dodgers and Clayton Kershaw. After getting shut out in back-to-back games (Game 2 and 3), the offense finally woke up in Los Angeles. When they returned to Wrigley for Game 6, Kyle Hendricks outdueled Kershaw in a masterpiece. The Cubs were going to the World Series for the first time since 1945. People were literally weeping in the streets of the North Side. My buddy’s dad, who had been a fan since the 50s, told me he sat in his car and cried for twenty minutes because he honestly thought he'd die before seeing a pennant.
Game 7: The Greatest Game Ever Played?
Let's get into the weeds of that final game. It started perfectly. Dexter Fowler hit a lead-off home run—the first time that had ever happened in a World Series Game 7. By the middle of the game, the Cubs led 5-1. It felt like a blowout. David Ross, in the final game of his career, hit a home run off the dominant Andrew Miller. Everything was going right.
Then Joe Maddon got cute.
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He pulled Hendricks early. He brought in Lester on short rest, who gave up two runs on a wild pitch. Then he brought in Chapman, whose arm was basically falling off from overuse. When Rajai Davis hit that line-drive homer over the left-field wall, the sound in Cleveland was deafening. The Cubs had choked. Or so it seemed.
The Meeting in the Weight Room
During the rain delay, Jason Heyward pulled the players into a small room. This is the part of the story that sounds like a movie script, but it’s 100% true. He told them: "I don't know how it's going to happen of how we're going to do it, but we're going to go out there and win this game. We're the best team in the world, and we're the best team in this park for a reason."
- The 10th Inning: Kyle Schwarber, who had missed almost the entire season with a torn ACL and miraculously returned for the World Series, led off with a single.
- The Pinch Runner: Albert Almora Jr. took his place and made a heads-up play to tag up to second on a fly ball.
- The Hit: Ben Zobrist, the ultimate utility man, laced a double. He became the World Series MVP for a reason.
- The Insurance: Miguel Montero drove in another run to make it 8-6.
In the bottom of the 10th, Mike Montgomery came in to get the final out. Michael Martinez hit a weak grounder toward third. Bryant’s smile as he threw to Rizzo is the image every Cubs fan has burned into their brain. 8-7. Final.
Why the 2016 Win Still Matters
It’s easy to look back now and say, "Well, they had the most talent, of course they won." But baseball doesn't work like that. The 1906 Cubs won 116 games and lost the World Series. The 2001 Mariners won 116 and didn't even make it.
The Cubs won the World Series because they survived the psychological pressure of an entire city's desperation. Every time a goat was mentioned or Steve Bartman’s name came up, these players shrugged it off. They were too young and too confident to care about curses.
Misconceptions About the Curse
Let’s be real: the "Curse of the Billy Goat" was always a bit of a marketing gimmick, but it represented a very real culture of losing. For decades, the Cubs were a "destination" for fans because of the ivy and the day games, not the product on the field. 2016 changed the DNA of the franchise. It turned the Cubs into a big-market powerhouse that was expected to win, rather than a quirky underdog that was expected to fail.
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Actionable Takeaways for History and Baseball Buffs
If you want to truly appreciate how this happened or apply these lessons to your own life or business, look at these specific drivers of their success:
1. Invest in the "Core" but Stay Flexible
The Cubs built around a specific group (Rizzo, Bryant, Báez) but weren't afraid to make a ruthless trade (Chapman) when they saw a window. Loyalty is great, but timing is everything. If you see a chance to win, you have to take the risk, even if it’s expensive.
2. Cultural Leaders are Underrated
Jason Heyward’s statistics in 2016 were, frankly, terrible. He hit .230 with 7 home runs. By any analytical metric, he was a bust that year. But without his leadership and that rain-delay speech, they probably lose Game 7. Don't overlook the "glue" people in any organization.
3. Use the "Rain Delays" to Reset
When things go sideways—whether in a game or a project—take a beat. Most people panic when momentum shifts. The Cubs used those 17 minutes to breathe and remind themselves of who they were.
4. Study the Box Scores
To really get the nuance of that series, go back and look at the PitchFX data for Game 7. Look at how many sliders Chapman threw because he couldn't find his fastball. It’s a masterclass in "gritting it out" when you don't have your best stuff.
The 2016 World Series wasn't just a sports story. It was a 108-year-old weight being dropped. It proved that eventually, if you build a system based on sound logic and resilient people, the math eventually works in your favor. Even if it takes a century.
To dig deeper into the stats, check out Baseball-Reference's 2016 World Series page for a pitch-by-pitch breakdown. For the emotional side, nothing beats the documentary The 2016 World Series, which captures the raw reactions in the locker room.
Next time you’re facing a daunting task, just remember: if a team can go 108 years without a win and come back from 3-1 down in the rain, anything you're dealing with is probably manageable.