The Wild Ride of a Millennial Chicago Sports Fan


Being a millennial Chicago sports fan, I’ve come to accept that the world has cycles of pain and joy; frustration and elation.

I’ll take you back to the start. It’s the nineties- and life is good. Our parents (baby boomers) are starting to get rich, we’ve got Bill Clinton cold opens on SNL, and Michael Jordan is proving to be untouchable. Six rings.

Disappointment wasn’t even in our vocabulary yet. Then, in a signal to a new era, the end of a cycle; Y2K ushered in the 2000s era of uncertainty and frustration.

Y2 Nay

In the sports world, we now see Jordan in a Wizards uniform. The Bulls put their hope in Elton Brand with the first pick of the ’99 draft. Woof. And remember Bartman?

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No, not him.

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Yes. Him.

Of course you do- it’s like asking a boomer where they were when JFK was assassinated. From 1998 until 2005, we have no championships from other Chicago teams to lessen the sting. Tough days.

This is what happens when people stop being polite, and start being real

In the real world, we have the tech bubble crashing and 9/11, bringing new, visceral emotions of tragedy and loss. Our rose colored glasses were smacked from our face as our worlds take on a darker tone. Millennials are getting older and our heroes have different uniforms. We’re starting to grow up.

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The second half of the 2000s brought hope in the Chicago sports world. The South Side brought a World Series everyone (including ESPN) seems to forget about, The Bears went back-to-back in the NFC North including a trip the the Super Bowl, and the Cubs flirted with ending the unforgettable drought.
















The smell of hope was in the air. And in the most unlikely of places, the Chicago Blackhawks regained their pulse with the end of their owner’s.

With Bill Wirtz’s death and transfer of control to his son, the Blackhawks began one of the most exciting eras in Chicago sports history.

Our country had issues (housing crisis) that we need to deal with, but things were not all bad. In addition to Chicago sports regaining life, Uncle Barry got elected president.
























Barack Obama, 2008

Chicago was on the cultural map in a big way. And whether you liked his political leanings or not, seeing Obama’s election brought most people hope for a new chapter in America.

Windy City rolling

The joy of the The 2010s started with a bang- the Blackhawks win the Stanley Cup. I was too busy swamped in Finance homework to appreciate the playoff run, but the crowds at NIU made it clear. We would become champions.

Then again in 2013. We looked good again in 2015. I remember it like it was yesterday. On a Cubs rain delay, Wrigley field flocked to the bars to watch game 7 of Western Conference finals: Hawks vs. Ducks in Anaheim.

No room in the case for participation trophies

We’d go on to win the Stanley Cup, and wouldn’t you know- the Cubs looked like a real team. The peak of our joy was just around the corner. The Cubs were getting close. The unthinkable was now thinkable.

Despite my rant induced by the Mets pitching staff and an open bar at a Lake Geneva wedding, I could feel the embers of hope in 2015. We were gonna do it next year.

Long story short, Hawks won. Chelsea Dagger was blaring, women were dancing on tables wearing shirts with ‘My Cup Size is Stanley’ written on them, and the city was a party.
























And we did. After winning game 7 in Cleveland, everyone including me took a pilgrimage to Wrigley Field on that fateful night. Did it make sense? Not quite, considering the Cubs were hundreds of miles away.

But it was instinctive, pay tribute at the Mecca. Helicopters whizzed overhead in a surreal moment when no one knew exactly what to do. There were celebrations, for sure, but collectively the feeling was that of a dog who had finally caught the car. What now? Drink a Hamms and cry, I guess.

The afterglow

In a further mirroring between Chicago sports and society, the unthinkable and surreal happened. Just days after the Cubs win the World Series, Donnie gets elected president. What now? Drink a Hamms? Definitely. After that? Who knows.

Maybe you hated it, maybe you loved it. It was our generation’s version of the OJ trial, splitting society into two parts. The person next to you may have very different views. Is that okay?

It’s all cyclical. Highs and lows. These have been the cycles of a millennial Chicago sports fan. Since 2016 there have been more lows- both in society and in Chicago sports. Names have been scratched from the Stanley Cup.

Cubs and Bears futility has been maddening. In society… well I won’t waste words. Having my building in the loop boarded up for months on end tells you everything you need to know. But in Chicago and America, we have the luxury of hope because we have great people.




























Dark times have a way of forging great leaders in Chicago; Jordan, Toews, Rizzo. America is no different. Just look for the man or woman who’s been through hell and is still working, that’s who you want to follow if you want a ring.

And if you’ve got a minute, turn on the Bulls. Zach Lavine might be next in the line of legendary Chicago leaders forged from very dark times.

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