Wrigley Field felt like a funeral home on October 30, 2016. I remember the air. It wasn't just cold; it was heavy with that specific brand of North Side dread that had been fermenting for over a century. The Cleveland Indians were up 3-1 in the World Series. History said the Cubs were dead. Most fans, honestly, were just hoping to avoid seeing a trophy raised by another team on their own grass. But then, the Chicago Cubs Game 5 happened, and everything shifted in a way that stats alone can't really capture.
People always talk about the rain delay in Game 7. They talk about Ben Zobrist’s double or Rajai Davis almost breaking the space-time continuum with that home run off Aroldis Chapman. But you don't get to Game 7 without the absolute grinder that was Game 5. It was the night the "Loveable Losers" tag finally felt like a lie.
The Night the Season Almost Died
The pressure was suffocating. If you look at the win probability charts for that night, the Cubs started the game with their backs against a jagged cliff. Trevor Bauer was on the mound for Cleveland, and despite his issues earlier in the series, he looked sharp enough to end it. Jon Lester, meanwhile, was carrying the weight of a city on his left shoulder. He wasn't perfect. He gave up a solo shot to Jose Ramirez in the second inning that made the entire stadium go silent.
That silence was terrifying.
It was that "here we go again" feeling. You've felt it if you’re a Cubs fan. It’s a physical weight. But the 2016 team was built differently—Theo Epstein didn't just recruit for talent; he recruited for "makeup," which is basically scout-speak for "guys who don't freak out when everything is on fire."
Kris Bryant, who was the NL MVP that year, decided he wasn't ready for the season to end. In the fourth inning, he took a 1-1 pitch from Bauer and parked it in the left-field bleachers. That home run didn't just tie the game; it punctured the tension. It was the first time in days that the Wrigley crowd actually sounded like they believed.
Three Runs and a Prayer
The fourth inning was the whole season in a microcosm. After Bryant's blast, Anthony Rizzo doubled. Ben Zobrist singled. Then Addison Russell—who had a massive postseason despite the off-field controversies that would later define his career—beat out an infield single to drive in a run. Javier Baez followed it up with a bunt. A bunt! In the biggest game of his life! It was chaotic and messy, and it resulted in a three-run outburst that would be all the Cubs would get.
Lester settled in. He went six innings, giving up two runs and striking out five. He did exactly what a $155 million pitcher is supposed to do: he gave them a chance. But the real story, the one that still makes my arm ache just thinking about it, was what happened next.
Joe Maddon’s Massive Gamble with Aroldis Chapman
We have to talk about the eighth out. Usually, you bring in your closer for three outs. Maybe four if you’re desperate. Joe Maddon brought in Aroldis Chapman in the seventh inning. The seventh!
- Out 1: Lindor strikes out.
- Out 2: Napoli flies out.
- Out 3: Santana pops up.
That was the seventh. Then came the eighth. Then came the ninth. Chapman threw 42 pitches. For a guy who lived and died on 100-mph fastballs, that’s an astronomical number. It was desperate. It was arguably reckless. Some analysts, like Tom Verducci, have pointed out that this heavy usage almost cost them the series in Game 7 when Chapman clearly had nothing left in the tank. But in the moment of Chicago Cubs Game 5, it was the only move.
Maddon knew there was no tomorrow. If you don't win Sunday night, Monday morning doesn't matter. Chapman’s performance that night was a gritty, sweating, terrifying masterpiece. He ended the game by striking out Jose Ramirez on a 101-mph heater.
Wrigley erupted. It wasn't the "we won the World Series" roar, but it was a "we're still alive" scream. There’s a difference.
Why We Get Game 5 Wrong
Most people think of this game as just a bridge to the drama in Cleveland. That’s a mistake. Game 5 was where the psychological hex was broken. If the Cubs lose that game, they are just another "what if" story. They’re the 2001 Mariners or the 1906 Cubs—teams that were dominant in the regular season but choked when the lights got bright.
Instead, they became the first team since the 1985 Royals to come back from a 3-1 deficit by winning the final two games on the road. But that road trip only happened because they defended their home turf one last time.
The Lester Factor
Jon Lester’s legacy in Chicago is basically cemented by this start. He didn't have his best stuff. His inability to throw to first base was a constant anxiety-inducer for everyone in the stands. Cleveland was leading the league in aggressive baserunning, and every time a runner reached, it felt like a disaster waiting to happen.
Lester ignored it. He focused on the plate. He pounded the zone. It was a professional, veteran outing that stabilized a young dugout. You can’t overstate how much guys like Bryant and Baez looked to Lester in those moments. He was the guy who had been there with the Red Sox. He knew how to breathe when the air got thin.
The Strategy That Nearly Backfired
While we celebrate the win now, we have to acknowledge the nuance. Maddon was criticized—rightly so—for how he handled the bullpen. By burning Chapman for eight outs in Game 5, he forced the rest of the series into a precarious position.
If Chapman doesn't have that superhuman Game 5, does he have more zip in Game 7? Maybe. But baseball isn't played in a lab. It’s played in the dirt. The Cubs were facing a Cleveland team that felt like a buzzsaw. They had Andrew Miller coming out of the bullpen looking like an unhittable alien. The Cubs had to punch back immediately, or they were going to be swept out of their own stadium.
What This Means for Today’s Game
When you look at modern postseason baseball, you see the "Game 5 Blueprint" everywhere. Managers are much quicker to pull their starters. High-leverage relievers are being used in the 6th and 7th innings. The "closer" role is becoming more fluid. Maddon’s usage of Chapman was a precursor to the "positionless" pitching we see in the playoffs now.
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But it takes a specific type of player to pull it off. You need a Chapman. You need a Lester.
Honestly, the 2016 Cubs weren't just talented; they were incredibly lucky that their stars peaked at the exact same moment. Bryant’s power, Rizzo’s leadership, and Chapman’s arm all converged on that Sunday night in October.
How to Relive the Magic
If you’re looking to dive back into the specifics of this game, there are a few things you should actually do rather than just reading a box score.
First, go find the raw broadcast footage, not just the highlights. Watch the crowd between pitches. The tension is palpable. You can see fans literally holding their breath.
Second, look at the pitch sequences Chapman used against Francisco Lindor in the 7th. It was a masterclass in intimidation. He wasn't just throwing hard; he was throwing with a purpose that said, You are not winning tonight.
Practical Steps for Any Cubs Historian:
- Watch the "Season 414" Documentary: It gives a much more intimate look at the clubhouse vibes during the 3-1 deficit.
- Analyze the 4th Inning: Don't just watch the Bryant homer. Watch the Addison Russell infield single. It’s a lesson in "hustle over exit velocity."
- Check the Statcast Data: Look at the spin rates on Lester’s cutter that night. It was jumping. Even without his "A" game, his movement was elite.
- Visit the Marquee: If you're ever in Chicago, stand under the marquee at Clark and Addison. Think about the fact that on the night of Game 5, thousands of people were standing right there, not even in the stadium, just wanting to be near the energy.
Game 5 didn't give the Cubs a ring. Not yet. But it gave them the right to keep fighting. In a century of failure, that Sunday night was the moment the "Curse" actually started to crack. It was gritty. It was loud. It was exactly what Chicago needed.
By the time the team boarded the plane for Cleveland, the momentum had shifted. The Indians were the ones looking over their shoulders. The Cubs were the ones playing with house money. And it all started with a 3-2 victory that was way closer than it should have been, but exactly as dramatic as it needed to be.