Wrigley Field is a little over a mile north of where I live, close enough that on summer nights when the “Friendly Confines” hosts a concert (August saw both Billy Joel and Pearl Jam), familiar ballads fill the courtyard of my prewar walk-up, prompting tenants to abruptly open, or close, their windows. Technically I don’t live in the same neighborhood as the Cubs—that would be Wrigleyville, the residential enclave surrounding the 102-year-old park—but for more years than most Chicagoans care to think, a steadfast devotion to the team has had a way of uniting the various neighborhoods on the North Side in a shared community of suffering.

In the seventies, when the team consistently flirted with the worst record in baseball, the Cubs earned the nickname the “Loveable Losers.” The qualifier is a tribute to the loyalty of the fans, but it hardly redeems the category. Say what you will about history, tradition, and heroic team players—and the Cubs have all three in abundance—this is still sports, and sports is about winning. The Cubs have not won a World Series since 1908. They have not even gone to the World Series since 1945. When Saturday night began, these records remained, though it looked as if, at long last, at least one of them might finally be broken.

Now, when something historic happens in your neighborhood, it seems a little rude to remain aloof. Still, even in the face of a 4–0 lead, I waited until the fifth inning to make my way north. Such is the restraint of lessons learned. On the few occasions in the past seventy-one years when it looked like they might snap their dreadful streaks, the Cubs have proven adept at squandering destiny. In 1969, they ceded a seventeen-and-a-half-game lead in the final quarter of the season to let the Miracle Mets slip into the playoffs. In 2003, up three games to two over the Miami Marlins in the National League Championship, they gave up eight runs in the eighth inning, trading away a 3–0 lead, a win, and, a day later, the pennant. Try as you might to banish such memories, they temper your enthusiasm and leave you a little paranoid about bad omens.

I worried I’d found mine in a fire truck that turned onto Clark Street just ahead of me. (Silly, I know, but, except for Labor Day parades, their appearance is inevitably foreboding.) One of the most famous streets in Chicago, Clark heads right by Wrigley Field, grazing the west side of the stadium. The sidewalks were surprisingly quiet until I reached Belmont Avenue, where a line of bars and restaurants begins. There, televisions flickered inside every establishment, giving a glimpse of the game to the would-be patrons, pressed against the picture windows. They supplied their own implicit play-by-play, gasping at close calls, cursing missed opportunities, and cheering any blow to the Dodgers as they staggered through the fifth. At Clark and Aldine, a surround-sound scream confirmed a home run for me. The lead was now 5–0.

By then, the sidewalks were so awash in royal blue that when an interloper appeared—a young man in a trench coat with gray glasses and frosted tips, waiting uneasily in a doorway—I felt moved to offer him bus fare. He was the last one I saw that evening. Everyone else embraced the moment, as sports fans do, wearing their loyalties on their sleeves.

By the time I got to West Newport, near enough to hear the roar of the crowd at Wrigley, I saw the cordon I expected. The cops had blocked off the quarter-mile stretch of Clark that remained before the stadium, making for something of a strange sight. Into the distance, the bars at either side of the street bulged with people, but the street itself was basically empty.

I headed west briefly, passing a few children squatting beside a firepit, and turned north, again, into the alley. With over nineteen hundred miles of these minor roadways, the Windy City is the country’s alley capital, and I thought the odds were fifty-fifty that Chicago’s finest would have blocked off the obvious workaround. But there were no troopers in the alleyway, not yet at least, just a steady trickle of celebrants, all moving double-time. Some of them darted east along the gangways to infiltrate Clark, but most continued north, hoping to get a glimpse of the stadium before the cops caught wise.

The covert route took us all the way to Addison, the crossbar to Clark Street, which together cradle Wrigley. There, beside the venerable Taco Bell, a sight as familiar to Cubs fans as it is truly odd to everyone else, a small crowd milled at the edge of the parking lot between the TV trucks and a makeshift barrier. At a diagonal, we were just across the street from the most famous sign in baseball, the candy-cane colored WRIGLEY FIELD, HOME OF THE CHICAGO CUBS . It was the bottom of the sixth, and the sign affirmed the Cubs were still up 5–0. You could have pinched us: we felt like we were dreaming

We were, of course, at least in one respect, for within a few minutes, the cops began dispersing us. Someone beside me tried to make the case on behalf of the group: We weren’t making any trouble, were we? The lady in blue shook her head regretfully. “If everybody would behave like this …” she said, letting us complete her sentence.

We were driven one block west to Racine, and I promptly turned north, again, thinking I might circle the perimeter and try my luck from the opposite side of the stadium, when I saw a few souls depart from the sidewalk and dart east again into another alley. I followed, passing alongside a house with a party inside. At the top of the steps stood what seemed to be the master of ceremonies, awaiting a tardy guest. “It’s not that hard to get here,” he said to a young man who was heading toward us. The young man smiled ruefully. “Man—fuck you!”

We passed into what had been the parking lot of a recently defunct McDonald’s but is now the edge of a construction zone for something called the Hotel Zachary. The ballpark is surrounded by these sites, many of which are part of the master plans of the Ricketts family, who bought the Cubs in early 2009, to turn Wrigleyville from a middle-class neighborhood that just happens to host a ballpark into a gilded Mecca of the Major Leagues. I have my reservations—sports fans are tories by nature, they want nothing to change about their team traditions—but that night I wasn’t complaining, for the worksite afforded a sheltered sidewalk, just on the other side of the street from Wrigley.

We filed behind the new barrier as “Sweet Home Chicago” began swelling inside the stadium. Again, we were tickled by our good fortune. Looking up Clark Street, just north of the ballpark, we could see the cops standing watch over the waist-high metal gates that separated them from a tide of revelers several thousand deep. Looking down Clark Street, we saw the ill-fated intersection from which we had been ousted, no more than five minutes before. “They can’t control shit,” one guy boasted, as if courting a second eviction.

It took only a few minutes. A group of the cops who had cleared out the earlier gathering came over and told us, quite firmly, that we could loiter elsewhere. “This is what is going to kill the crowd,” one spectator sulked. The patrolman seemed less sympathetic than his colleague. “Tell the mayor,” he suggested.

Arguing with armed men is pretty far from my comfort zone, so I quickly retreated. But when I arrived again at the edge of the covered walkway, I noticed that the cops who were manning the gates north of us seemed indifferent to a trio who had just casually crossed the street. Reminding myself not to sprint, instantly I followed. In a moment, I was standing beside Wrigley.

The small plaza was nearly deserted. A few attendants still lingered beside the arches of empty metal detectors, a handful of people collected before the VIP entrance between the ticket booths and the front gates. A large window looks inside the waiting room there, so even when you’re standing outdoors, you can watch the television behind the security desk. I joined the assembly as the top of the eighth began. One woman excitedly observed that we were six outs away from the World Series. “Shut up!” her friend protested, convinced she might be spooking it.

By my count, there was a sixteen-second delay between the action on the field and the evidence on television, so the reactions of the crowd, no matter their tenor, taunted us with anticipation. Inside the VIP entrance, a woman with white hair wearing an employee jacket paced the room nervously. Her hands were folded before her, as if they were ready for an emergency prayer. On the screen behind her, the faces of the crowd were furrowed and grimaced. Someone who knew nothing of their suffering would never have guessed their team was up 5–0 at the beginning of the ninth inning.

The Cubs secure the first out, but then something happens inside the stadium, and we try to interpret the groan. “I think that’s a hit,” the one lady ventures. “Just win it,” says her friend. Ball four finally appears on the television, and the batter heads to first. For us, the next batter is heading to the plate, when inside Wrigley, something happens. A roar goes up, a miraculous roar. What is it? Could it be? It must! Oh my God!

We’d waited seventy-one years. We could wait sixteen seconds more.

John Paul Rollert is a writer in Chicago. His work has appeared in the Los Angeles Review of Books, Boston Review, and the New York Times.