The Heartbreak and Joy of Being a Lifelong Cubs Fan

What the historic World Series win taught me about about disappointment and forgiveness

Charlie Riedel / AP

It was October 15, 2003, ten days before my tenth birthday. The previous night, the Chicago Cubs had been five outs away from returning to the World Series for the first time in 58 years, before the most infamously cataclysmic half-inning in the history of the franchise had forced a Game 7.

There were two outs in the bottom of the second and a runner on third, the Cubs were down 3-1, and the pitcher was up to bat. Kerry Wood was an exceptionally good hitter for a pitcher, but he was still a pitcher, and this was still the National League Championship Series, and these were still the Cubs.

I was sitting at home on the couch with my mom, my hands clasped together, my chin resting on my hands, watching Wood go deeper and deeper into the at bat. 0-1 … 1-1 … 1-2 … 2-2 … Full count. And then: a swing, a hit, a long fly ball to left center, Wood running around the bases, Wrigley going wild, the announcers going wild, me going wild, our phone ringing.

My mom ran over to pick it up, and it was my dad, who was at Wrigley Field with my older brother, on the other side of the line. She could barely hear his words over the crowd, still cheering as Wood walked off the field: “Do not emotionally surrender to this team.”

What my dad didn’t know, but probably suspected, was that I already had.

I had surrendered because I loved that team—in fact, it was the first team I had ever loved. I loved Moises Alou out in left, and I was worried he felt guilty about the Bartman incident in Game 6. I loved Mark Prior and Wood, no matter if they were throwing strikeouts or giving up home runs. I loved Alex Gonzalez, having quickly forgiven him for letting that ground ball go through his legs the night before. I loved Mark Grudzielanek and Corey Patterson, Aramis Ramirez and Hee-Seop Choi, Kyle Farnsworth and Damian Miller, all despite their flaws. I loved Sammy Sosa and was adamant he wasn’t on steroids. (He was.)

What my dad didn’t just suspect, but probably knew, was that that team, the one I loved, was going to lose, and it was going crush me.

They did, and I was.

In mid-October 2003, I had never driven a car, left the country, or dyed my hair. I was yet to cast a ballot, open a bank account, go though a breakup, or even go on a date. I doubt I had ever done a load of laundry. At nine years old, I hadn’t experienced much, and the Chicago Cubs—by losing that game 9-6 and dashing the dream of a World Series on the North Side—had just taught me about heartbreak.

But even for a die-hard 9-year-old Cubs fan, baseball isn’t everything. That night turned into the next day, and that day turned into the next week. Nine turned into ten. October to November. 2003 to 2004. Elementary school to middle school. Middle school to high school and high school to college. I still went to games, I still cheered, and I was still a fan. But now, when Alfonso Soriano dropped a ball out in left, I wasn’t so quick to forgive. When Derrek Lee struck out in a big moment, I wasn’t so quick to forget. I had learned that being a Cubs fan was about balancing naïve optimism and relentless pessimism, and I was determined to never again let the former eclipse the latter.

Then, came this year.

For the first time in 13 years, I found myself a little too excited. I was a little too happy when they won, a little too sad when they lost. The advantage of supporting a team that hasn’t won since a decade before the dissolution of the Austro-Hungarian Empire is that you barely notice losing most years. When other teams are bad, their fans are sad. When the Cubs are bad, we just are.

The author in 2003

We watch the games, we pick our favorite players, we talk about the farm system, we drink our beers, and of course we cheer when they win, but we rarely expect them to. But every once in a while, when a really good team comes along, you find yourself thinking, just thinking, that maybe, just maybe, this might actually be the year. While this alone isn’t dangerous, the inevitable loss after you dare to hope—as I had learned back in 2003—will crush you with the weight of a thousand defeated Yankees, Giants, Marlins, and Phillies teams. So when I came home for Easter this past spring and went to Wrigley, and it smelled a little too good and the hot dogs tasted a little too fresh, I was worried. But then again I wasn’t, because I was still a Cubs fan, and this team was just so good.

By the time October rolled around this year, I had lost the battle—I was stoked. On the night they won the NLCS, my roommate and I started looking at tickets to fly home for that weekend and Games 3, 4, and 5. We thought we might be lucky enough to be in Chicago the night the Cubs won the World Series. Of course they went down 3-1. And of course we were fools—we’re Cubs fans.

They were going to lose, I told myself. But it was okay because I was prepared this time. But then they won Game 5. And Game 6. And suddenly, we found ourselves facing another Game 7.

Last night, as I watched Kris Bryant field that final out to make the Chicago Cubs the World Series Champions for the first time since 1908, I realized it was only then, in that very moment, that I was finally able to forgive that 2003 team. It sounds ridiculous, because it is. And now that I’m typing it, I wish I weren’t. But for more than a decade I had refused to truly love the Cubs, because when I was nine years old they had broken my heart.

Every Cubs fan has a story, and this is just mine. But it’s my suspicion that many of us are forgiving some team or another today. And if not some team, then some player, or some coach, or some umpire for that series, or that game, or that play that taught us to never emotionally surrender again. And that’s not a totally terrible thing.