For as long as I can remember, being a Cubs fan was less about baseball and more about belief.
Not belief in winning—not really—but belief in the act of believing itself. The kind passed down by fathers and mothers and the grainy glow of a daytime WGN broadcast. I was born a Cubs fan, but my first memories of being a Cubs fan are from the 1970s, sitting cross-legged on my Granny's living room floor, watching Jack Brickhouse call day games from Wrigley Field. Hey-hey! The sun always seemed to shine a little brighter through those dusty windows, and for a few hours, the Cubs were everything. My mom, my grandparents—they all loved the Cubs. But it was my great-grandmother’s house where that love was sealed. That’s where I learned how to sit still for nine innings and how to hold onto hope even when the standings didn’t make any promises.
Cubs fandom wasn’t a hobby—it was a lineage. And it came with its fair share of heartbreak.
In 1984, I paid a lot of money for tickets to see the Cubs play in the National League Championship Series. They were up two games to none against San Diego—and then lost three in a row at Jack Murphy Stadium. I was there. I watched it slip away in real time. Five years later, in 1989, the Cubs were back in the NLCS—this time against the Giants. And after San Francisco won the series, I remember feeling something strange: guilt. Because when the Loma Prieta Earthquake hit just before the World Series, a small part of me wondered if it was a sign from God that the Cubs were supposed to win—that the world itself had tried to intervene.
But I kept watching. Always. Through the 1990s and early 2000s, WGN was still my summer companion, and Harry Caray's voice—raspy, joyful, half-in-the-bag by the seventh inning—was the soundtrack to my hope. "It might be... it could be... it is!" he’d shout, and for a few moments, you'd forget how many games back we were. Even in the losing seasons—and there were plenty—I’d find myself drifting back to that kid sitting on the floor at my great-grandmother’s house, watching day games and believing, simply because that’s what we did. We hoped. We waited. And Harry helped make that waiting feel like something close to joy.
Then came the Lou Piniella era, and for a little while, it felt like we were onto something real again. In 2007 and 2008, the Cubs looked like contenders—good ones. They won the division both years, the team was balanced, confident, and tough. I let myself believe, just a little more than usual. But then came the postseason, and with it, the gut punch. Swept out of the NLDS two years in a row—first by the Diamondbacks, then by the Dodgers. The hope I had carefully built was flattened. Not because we lost, but because of how we lost. Swiftly. Quietly. Like we didn’t belong there after all.
Then came 2003. The Bartman Ball. My son and I sat together and watched as the Cubs fell apart against the Marlins. It wasn’t just a loss—it felt like a family wound. I remember wondering, with real fear, if I was just another link in the chain—if generations of my family had lived and died without seeing the Cubs win it all, and if I was about to pass that legacy down to my own kids.
And yet—despite everything—I kept watching. I kept hoping.
The 2016 World Series itself was a gauntlet of emotion. The Cubs had finally made it—and after everything, that almost felt like enough. But of course, it wasn’t. Not now. Not when we were this close. Then came the Cleveland Indians, and a series that turned every inning into a cardiac event.
When the Cubs fell behind three games to one, it felt like fate had returned to finish the job. I told myself I’d seen this movie before. That maybe I should spare myself the heartbreak. But I couldn’t not watch. It was like waiting for a train wreck I couldn’t look away from—slow, inevitable, painful.
And then came Game 5 at Wrigley. Elimination night. Lester on the mound, the offense still tight, the crowd a knot of hope and fear. The Cubs scratched out a 3–2 win, barely holding off Cleveland, and you could feel the gears start to turn. Kris Bryant homered. David Ross caught the final out. It wasn’t dominance, but it was life. The kind of game that reminded you why we watch—because even in the darkest moments, there’s always a chance.
Then Game 6 in Cleveland. Arrieta was sharp, the bats came alive, and suddenly—suddenly—the Cubs looked like the team we’d watched dominate the regular season. Bryant went deep. Russell hit a grand slam. The Cubs scored early and often. It wasn’t close. A 9–3 win, the series tied, and all bets were off. They hadn’t just forced a Game 7—they’d swung the emotional pendulum completely. From dread to fire. From “here we go again” to “maybe this is the year.”
Somewhere deep down, I started to believe. Not with bravado. Not with certainty. But with that quiet, familiar flicker that’s carried Cubs fans through lifetimes.
So on November 2, 2016, when Game 7 of the World Series stretched into its tenth inning, it felt less like a baseball game and more like a reckoning. Rain had paused the world, the score was tied, and a century of ghosts seemed to lean in a little closer.
I watched that game from my living room, surrounded by people who weren’t nearly as emotionally invested in the Cubs as I was. They knew I cared—knew it mattered—but they didn’t feel it in their bones the way I did. Still, they watched with me, patiently riding the emotional roller coaster, quietly supportive while I paced, shouted, swore, and occasionally buried my face in my hands. I was alone in the depth of it, but I wasn’t alone—and somehow, that made the night feel even more intimate, more personal, like I was carrying the weight of generations all by myself in that room.
The highs and lows of that night were biblical. Fowler’s leadoff homer felt like a miracle. Baez going yard, Ross’s redemption. A 5–1 lead in the fifth. A 6–3 lead in the eighth. And then, suddenly, it started slipping.
Chapman came in—overworked, exhausted, human—and just like that, the ghosts showed up. Davis homered. The game was tied. The stadium in Cleveland thundered, and a familiar voice started whispering in my head: We blew it again.
It wasn’t a thought. It was a reflex. Nearly every ounce of my body was screaming that we’d seen this before, that we’d lived it before—Brant Brown, Bartman, black cats, Leon Durham, the curse of whoever you chose to blame. All of it suddenly alive again in the worst possible way.
But I didn’t turn away. I didn’t shut it off. I just sat there—tense, sick, silent—and kept watching. Somewhere beneath the dread, I still hoped. Not in a loud or defiant way. Just a flicker. A little pilot light that had never quite gone out, no matter how many times the wind had tried.
And then the rain came. And the Cubs gathered in the weight room. And something shifted. I don’t know if it was divine intervention or just resilience forged by a century of heartbreak—but when they came back out, they looked different. And then Zobrist. And then Montgomery. And then Bryant grinning as he fielded that final grounder, slipping ever so slightly on the throw—almost too perfectly Cubs—and Rizzo stuffing the ball into his back pocket like a secret he never wanted to let go.
The room erupted, but I just sat there. Not out of disbelief, but because I didn’t want the moment to move past me too quickly. After 108 years, I had learned how to wait.
The next morning, I found myself watching a 30-second Budweiser commercial that had somehow appeared overnight. It featured Harry Caray’s voice, layered over scenes from the night before—Bryant to Rizzo, the dogpile, the scoreboard, the roar. I watched it over and over again. Hearing Harry call the Cubs’ World Series victory nearly two decades after his passing—it broke something open in me. That voice was the soundtrack of my summers, of my childhood, of the long, slow decades of hope and heartbreak. And here he was again, calling it home, just like he always did.
That video was the connection I didn’t know I needed—to my past, to the generations before me, and to the version of myself who had waited so long for this. I could live inside those 30 seconds. And maybe I still do. The same way a song can pin you to a summer, or a smell can send you back to your childhood bedroom, that video takes me straight to that night. I remember how it felt. I remember how I knew—knew—that nothing in baseball would ever mean more than this.
I thought about Wrigley. About the bricks and ivy that had seen so much futility and hope and human comedy. About the way that ballpark holds onto memory like ivy clinging to stone. I thought about all the times I walked into that place and looked out at the field like it was a cathedral. Because for many of us, it was.
The Cubs didn’t just win a championship that night. They untied a knot that had lived in generations of stomachs. They let us feel joy not as an abstract idea or a stubborn hope, but as something real, tangible, earned. And in doing so, they reminded us why we believed in the first place—not because we thought they’d win, but because we knew what it meant to keep showing up anyway.
There are a million stories from that night, and they’re all true. Mine just happens to be one of them. But the magic of November 2, 2016, is that it belongs to all of us. Every fan who waited. Every parent who passed it down. Every kid who first heard, “Just wait ’til next year,” and somehow believed.
Well—next year came.
And it was everything we dreamed.
