I remember sitting at a bus stop in Tallahassee, Florida, many years ago, talking excitedly about the Chicago Bulls. They were finally headed to the NBA Finals, and a few of us were going back and forth about what it meant.
Out of nowhere, some guy who wasn’t even part of the conversation jumped in and said,
“You’re stupid if you think the Chicago Bulls will ever win a title.”
Eight years later, the Bulls had won six NBA championships.
Three in a row.
Twice.
To this day, I wish I could see that guy again—just once—so I could give him the most ridiculous, satisfied smirk imaginable. That’s one of the privileges of being a diehard fan. Sometimes, patience gets the last laugh.
The Season Nobody Believed In
Last night, I watched the Chicago Bears play in the Divisional Round of the NFL playoffs—a game that capped off a season where most people didn’t think we’d win more than five games.
Instead, we:
- captured the NFC North division title
- beat the Packers twice
- knocked them out of the playoffs
- and finished two games away from the Super Bowl
The Divisional game itself came down to a route supposedly run in the wrong direction—one catch away from putting us in position for a game-winning score. I don’t blame the receiver. That game had plenty of moments earlier where things could have swung differently.
And let’s not forget one of the most ridiculous Hail Mary touchdowns passes I’ve ever seen in my life.
We were there.
We belonged there.
And nobody saw it coming.
There was something else that stuck with me during that game, too.
Last week, one of my high school friends posted that the Bears had lost—before they came back and beat the Packers. Last night, it happened again. In a group chat, he declared the game over just moments before we scored the game-tying touchdown that forced overtime and gave us a second chance.
If you ask me, that’s worse than Randy Quaid’s “this team rocks / this team sucks” character in Major League II—the guy who abandoned the Cleveland Indians right before they turned it around.
Today, they’re all planning a get-together in the Chicago area soon—a little high school reunion of sorts—partially to celebrate the Bears’ season. And if I’m being honest, part of me feels like fans who give up that quickly don’t really deserve to show up for the celebration when things finally go right. You don’t get to abandon ship the moment it starts rocking and then raise a glass when it reaches shore.
That being said, I’m not going to say anything. Some things are bigger than sports—even when sports mean as much as they do to us.
Chicago Teaches You How to Wait
When people say, “It’s hard being a Chicago fan,” they’re not wrong. That phrase has applied to almost every team we’ve loved at some point.
I’ve seen:
- the Bulls rise, dominate the 1990s, then fall hard afterward
- the Sting (now defunct) kicked their way to soccer championships in 1981 and 1984
- the Fire FC (MLS) win titles in 1998, 2000, and 2003
- the Blackhawks struggle… and then win three Stanley Cups between 2010 and 2015
- the Sky capture their first WNBA championship in 2021
- the Bears dominate football during the 1985 Super Bowl Shuffle season
Even the White Sox won a World Series in 2005—but that’s one Chicago team I don’t have any love for. You either love the Cubs or you love the White Sox. Rarely, if ever, both.
And then there were the Cubs.
The Cubs, My Father, and 2016
I spent many summer days sitting next to my father on the couch, watching Cubs games. Year after year, the frustration was the same. We always believed—maybe this year—while knowing, deep down, that history wasn’t on our side.
The so-called “Curse of the Goat” kept us waiting for more than a century for a World Series championship. And then there was the infamous 2003 Steve Bartman incident—which I don’t even want to talk about.
There were close calls. Painful playoff exits. Hope followed by heartbreak.
Then came 2016.
When the Cubs finally won the World Series, I screamed at the top of my lungs. I cheered. I laughed. And then I cried—harder than I expected.
Those tears weren’t just joy. They were relief. And they were sadness, too—because my father wasn’t there to see it. Neither was his father. Two generations who deserved to witness that moment.
I still remember seeing a news clip of a man watching the final game on a small TV at his father’s grave. When the Cubs won, he collapsed onto the headstone and cried.
Yes—we take our sports seriously in the Chicagoland area.
Loyalty Isn’t Always Convenient
I once had a friend—a diehard Bears fan—tell me she’d had enough. She was done with the humiliation, the disappointment, the pain. She switched her loyalty to the Pittsburgh Steelers.
I begged her to stick it out.
She said she couldn’t anymore.
I wonder if she dusted off her blue and orange this season. If she even has it anymore.
Me? I’m not that guy.
I stay.
Through the bad years.
Through the embarrassing years.
Through the seasons where rival fans line up to remind me how bad things are.
When they win, they gloat.
When we win, I don’t.
I just give that quiet, ridiculous smirk—the one that says,
“You were saying?”
Pride, Earned the Hard Way
I love my Chicago teams.
We’ve been there before.
And in time, we’ll be there again.
To the Chicago Bears:
Thank you for an incredible season. Hold your heads high.
They said we had no business being there.
But we were.
And something tells me—we’ll be back sooner than they think.
…and I don’t mind readjusting my trophy case.
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