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The thrill of victory and the agony of defeat: A long-suffering fan reflects on a semi-successful season

Madeline attended the White Sox's first 2021 playoff game with her dad.
Madeline attended the White Sox's first 2021 playoff game with her dad.

It’s hard not to be romantic about baseball.

It’s the only sport in which a guy who’s 5’6” can beat a guy who’s 6’7” in MVP voting. Despite its 150-year history, new records, no matter how miniscule, are set on a near-daily basis. Those in search of a pick-me-up can find an abundance of stories of players having the best games of their careers immediately after suffering a personal tragedy.

For those who love rooting for the underdog, the ballpark is paradise.

As a fan of a team who had not won a division title in more than a decade prior to this season, I know a thing or two about rooting for the underdog.

The best thing about baseball, though, is that the underdog sometimes wins.

Prior to the 2021 season, ESPN ranked the White Sox as the 7th best team in baseball. Not too shabby, but they were projected to end up with a record of 84-78 and given a 33% chance of making the playoffs.

That same article named center fielder Luis Robert as the team’s most exciting player. It also states that the Sox’s best case scenario – winning 95 games and the division title – could only be achieved if the team stayed healthy.

Just a few weeks into the season, Robert tore his hip flexor and would ultimately spend more than three months on the injured list. On June 9, rookie second baseman Nick Madrigal tore his hamstring – a season-ending injury. On July 5, slugging catcher Yasmani Grandal tore a tendon in his knee and was out for almost two months.

Taking into account star left fielder Eloy Jiménez’s spring training injury that kept him out of the lineup until late July, the Sox had an uncomfortably long stretch in which nearly half of their starters were on the IL.

They did a shit job staying healthy, and they didn’t win 95 games.

They won 93.

By the all-star break, our lineup was composed of random journeymen, rookies that were rushed through the minors to take over for injured starters, and just a few familiar faces that had escaped the injury bug.

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By the end of July, we had the largest division lead in baseball by a generous margin – nine games up on Cleveland.

This ragtag group of Sox seemed to have an aura of magic surrounding it – they won game after game against teams that were much better than them on paper.

When the team returned to full strength in late August, all bets were off. I knew my Sox were bound to make a playoff run.

Frankly, I didn’t know how to act.

Watching your team overperform after years and years of underperforming (or just straight-up sucking) creates a sort of impostor syndrome. 

Does this team really belong in the playoffs? Can they hang with these other star-studded clubs? What if it was all just a fluke, and they get knocked out in the first round?

I had to stop myself from spiraling into those thoughts, so instead, I reflected upon how we got here.

The Sox last made the postseason in 2008, not counting the abbreviated 2020 season in which everyone and their mother made it. I became a serious fan in 2009, which would be hilarious if it weren’t so sad.

For most of the 2010s, the Sox were mediocre at best, but it didn’t feel that way to me. Because I’d never seen a postseason team, I didn’t know any better. I still cheered loudly after every win and sulked for every loss, even if none of those games meant a thing because the team was firmly in third place.

As cheesy as it sounds, even though the team was mediocre, my experience as a fan was anything but.

Since I became a fan in 2009, I’ve watched two perfect games and two no-hitters by Sox pitchers. Not many fans can say that.

I’ve attended dozens of games and have sat in nearly every section of Guaranteed Rate Field. I’ve eaten more hot dogs with grilled onions and mustard than I can count. I ran the bases on the field on my 10th birthday. 

As a kid, I cried every time I went to the game and the Sox lost; I took it personally. At my first Crosstown Classic game against the Cubs, I dumped my Sprite on a Cubs fan in front of me and played it off as an accident. My only excuse is that I was 11 at the time.

I’ve poured countless hours into watching the Sox on TV. For years, I watched nearly every game in my basement with my dad; nowadays, I usually watch in my dorm room alone. It’s lonely, but I still text him continuously throughout the game.

I’ve spent the majority of my life loving the Sox, and even though I’ve always been competitive, the lack of winning never made me love that pathetic team any less.

Still, though, I had more than earned a postseason team. Keeping the faith during year after year of “rebuilding” isn’t easy.

As I prepared to witness my first ever postseason Sox team, I thought of that watery-eyed 10-year-old kid who agonized over every pitch of every game.

I thought about how proud she would be.


It’s 7:08 p.m. on a Sunday, and my heart is racing.

I’m at my very first playoff game, and Dylan Cease just threw his first pitch for a strike.

I was in my capstone class when my dad texted me saying he’d snagged two tickets to game three of the ALDS. I had to bite my lip to keep from audibly gasping.

The Sox were down 0-2 after dropping both games in Houston, so I knew there was a very real chance I’d be watching the Astros complete the sweep in-person.

Thankfully, that didn’t happen – the Sox did win that game. But they lost the next one and were eliminated, so my excitement about the singular win was short-lived.

The crowd remained hopeful until the very last pitch, though. When your team is in the playoffs for the first time in 13 years, you don’t just throw in the towel after two losses.

Being surrounded by 40,000 people who shared my excitement and desperation was an emotional experience. But, because there’s no crying in baseball, I suppressed my urge to tear up.

My dad caught my eye, though, and gave me a knowing look. He knew I’d been waiting my whole life for this.


On Oct. 1, 2012, the Sox destroyed the Cleveland Indians, 11-0.

It was a great win, but it was too little, too late – they would narrowly miss making the playoffs, despite being in first place for 126 days, after a horrendous spiral at the very end of the season.

I was devastated, of course, but my love for my team never wavered. I made that clear in a letter I wrote to the Sox that night, which I still have saved in my notes app to this day.

“Dear White Sox,

Many people would call me crazy for writing a fake letter to a sports team, but I am.

You have probably noticed that many of your fans are disappointed in your performance lately.

I’m not.

Sure, you’ve had some rough games, but you’ve had solid ones as well, and you’ve learned from your mistakes.

I wore my favorite Sox sweatshirt to school today, and many people said to me, ‘How could you wear that with the way they’ve been playing?’

I just told them, ‘It’s called faith. Ever heard of it, you Cubs fan?’ They just looked at me like I was crazy and walked away.

Maybe they hadn’t heard of faith. Or maybe they’re just ignorant.

Anyway, I just want you to know that I believe in you, even if no one else does.”