In my 23 years of life, I haven’t witnessed a lot of hometown greatness. My parents, on the other hand, watched seven of the greatest Chicago championship wins within the span of 12 years. 

My parents moved to Chicago in 1985, and a year later, they witnessed the Chicago Bears win a Super Bowl. Six years after 1985, they watched the Chicago Bulls’ first championship of the program. They went on to experience five more within the next seven years. 

I ask them too often what it was like to watch that Chicago Bulls team — Michael Jordan, Scottie Pippen, Dennis Rodman, Toni Kukoč, Steve Kerr and Horace Grant. Oh, the things I would do to be able to experience that era.  

In the past decade, I have witnessed five championships from three different teams. The most recent championship was the Chicago Sky in 2021. The Chicago Cubs won in 2016 and the Chicago Blackhawks won in 2010, 2013 and 2015.  

I’m giving those three teams a pass for now since we have some even worse teams on our hands. 

The Chicago White Sox haven’t won a championship in two decades. They won when I was three years old, so I do not remember it at all. In the 2024 season, they had the worst season in modern MLB history — modern history is anything after 1900. They won 41 games and lost 121, “beating” the 1962 New York Mets who lost 120 games. 

It’s been 124 years, and you’re really that bad? Yikes.

On May 6, the Chicago White Sox truly proved that they won’t be better anytime soon — Chase Meidroth had an unbelievably soul-crushing error where a ball bounced off his head. While that was only one play that one guy made, it sums up how the White Sox have been recently. 

Who knows, maybe Pope Leo XIV — who is a confirmed White Sox fan — will help the Sox somehow. 

While the White Sox are their own problem, the Chicago Bulls and Bears haven’t won a championship in the 21st century. Reread that sentence.

The Bears won the Super Bowl almost 40 years ago. 

The last championship the Bulls won was in 1998 — almost 30 years ago.

Basketball and football are considered the most popular sports in the United States. Why has it taken the Bulls and Bears so long to get better? 

Many people consider the double doink in the 2019 NFC Wild Card game as the Bears’ downfall. There have been nine different starting quarterbacks since that game.

The Chicago Bulls were quite bad this year, but the last 15 games they decided to get better, even though many thought they would tank to try and get a high spot in the 2025 NBA Draft. Before the Play-In Tournament, the Bulls won 11 of their last 15 games. 

Josh Giddey hit a buzzer beater that, according to some, didn’t help the Bulls in the draft lottery. They ended up with the 12th pick and the Dallas Mavericks — who traded their biggest star Luka Dončić a few months ago — ended up with the first draft pick. They only had a 1.8% chance to get the first pick… interesting. 

When there are good moments with Chicago sports teams, it’s like finding a needle in a haystack. 

One recent highlight of a Chicago sports team is that the Cubs’ Pete Crow Armstrong and Kyle Tucker this season have 10+ home runs and 10+ stolen bases. 

Who else is on that list with them? Shohei Ohtani, who won the National League MVP last season. 

I was able to see the 2016 Chicago Cubs World Series trophy in 2018 with my own eyes. But, I don’t like to admit this, I was asleep when they won the World Series. I woke up as everyone was cheering, and I have never felt more disappointed in myself. 

I guess I was so tired of eighth grade that I had to take a nap while the Cubs had a rain delay. Shoutout to my mom and dad for letting me sleep on the couch, but why didn’t you two wake me up?

Even though there are painful moments as a Chicago sports fan, I sit and watch every game like a good Chicago sports fan does. I will keep on hoping there will be a day where I can proudly say I’m a Chicago sports fan. 

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