“South Side, Sox Side.”: On the Great Migration and Segregation



Around certain people, it’s more than just a phrase. It’s a lifestyle; the unique battle cry adopted by a special group of folks in a special city. On the surface, it let’s everyone know that you root for the White Sox, and not the Cubs. But once unpacked, it means so much more.

It’s no secret: most of the Black people from Chicago grew up on the South Side. It’s been, and will likely be, a completely Black space for quite some time. Their winters are just as unforgiving as their summers are inviting and their music, food, and slang are all one-of-a-kind.

A rather long city, book-ended to the east by Lake Michigan and split across the middle by downtown, The North and South sides make up most of what we know as Chicago. And, like anywhere else, its dwellers root for the squad closest to home.

“South Side, Sox Side” brings life to the contradiction that is Chicago, the ring leader of the historically segregated Midwest. A city that, like the colors of its native White Sox ball caps, deals largely in black and white.

“I’m gonna find somewhere to put that thing… soon.”

Meet Christina. A good friend of mine and a Chicago native. She’s small, tidy, and vibrant, just like her apartment in the city. When you talk to her, she carries an infectious tone of voice that makes you just as eager to listen as you are to speak. Like many great communicators, she’s curious to her core, forever just as interesting as she is interested.

We met at work in Chicago in 2012. She was already employed, working a full-time job in corporate communications and I was a summer intern. Some of the only people in the office that looked like us, we struck an unofficial alliance almost immediately. She helped me navigate my early career, and to this day has never been too busy to lend an ear and a hand to a good idea or cause.

She works, travels, networks, and all the other things you’d expect from a modern millennial woman in a big city. Yet somehow manages to volunteer, do cross fit, mentor, and spend time with her family along the way.

I was shocked to even get on her schedule, to be honest, so when I walked in to the apartment and saw her making craft cocktails, I was thrilled.

I settled in for a sip.

“My parents downsized so now I have to take it back.”

She’s talking about a baby grand piano. She was the only one of her siblings to play it growing up, and now it’s monthly storage bill serves as an elegant reminder of both her Chicago childhood and the fact that she may have outgrown this tidy apartment. She has dreams of hosting dinner parties and making more homemade cocktails in a place big enough to also hold the piano, but for now, she’s renting; for the last time, she says.

“Once my mom’s family arrived from Georgia early in the Migration, they never rented. They weren’t perfect, or always successful, but they were smart; and that’s something to be proud of.”

As she talked about her history, she explained the early troubles her family ran across when they first arrived in the city. Her great-grandmother (rumored to be the product of rape by a white man) was extremely fair-skinned, and her great-grandfather was what she called “blue-black”. People assumed they were an interracial couple, which made it difficult to make a decent living in a city as segregated as theirs. But they pressed on.

“My folks were residential building owners on the South Side; they still own one of them to this day, actually. My great uncle and his daughter operate it.”

She explained that even though it’s a good fall back, she’d be including other areas in her search. As a young, single, high-earning professional, her options are endless.

However, it wasn’t long ago that her family’s South Side property would have been one of only a few options. Despite being founded by a Black man, and growing into one of the most diverse cities in the world, Chicago has never been able to shake the stench of segregation. It’s affected the city at-large from sports fandom to the neighborhoods themselves.


By the time the mid-1900s rolled around, Chicago’s Black population had grown by 250,000 people. The Great Migration was giving Black southerners the chance to chase the lives they’d dreamed of, but many never even made it as far north as downtown, coming straight from the South to the South Side.

Their plans to meet success and opportunity were thwarted with restrictive land covenants and other methods of “legal” segregation. Chief among them was redlining, which saw the FHA fence off certain residential and commercial areas to Black people and/or selectively raise prices to make it near impossible for us. This quite literally illustrated the limits to their newfound freedoms.

Like her family, many people did their best to make lemonade out of the lemons they were given, but it was only so much people could do in the severely overcrowded and underfunded conditions that made success an afterthought.

It was less than an ideal predicament, to say the least. Christina had a different way of describing it.


I took another sip.

“Listen. If your neighborhood and schools and environment all happen to be shitty, then your life just might turn out the same way!”

I felt her. What I saw in that moment was the ugly history that watched “post-segregation” Chicago put laws in place that have clearly disadvantaged people for decades. How can they have ever been expected to grow without the support of business and mortgage loans or decent paying jobs? How could their dreams afford to breathe if they couldn’t leave the South Side?


She’s from South Shore, a historically middle-class Black neighborhood once home to Michelle Obama and Jesse Jackson, and recalls being faced with the reality of not “being allowed” to go to the high school she grew up next to.

“Growing up charmed and still very Black has a way of making you skeptical of everything. Neighborhoods didn’t need to be gated, and people walked in and out freely, but young boys were still getting killed outside of the gas station up the block for their Jordan’s.”

Being skeptical of everything takes its roots in the burden that Black people carry due to the uncertainty of our identity. For as long as we can remember, most Black people have felt bits of both pride and shame in where we come from, in some instances having to pass brown paper bag tests just to live in certain Black areas. For them, being from the South Side was part willful choice, and part unfortunate circumstance.

The trauma.

“Even Black neighborhoods are segregated to a certain degree.”

Like her grandmother all those years ago, she saw it in her neighborhood every day growing up. And just like her mom, when it was time for her to choose her own school and enroll in college, she chose Northwestern, a predominantly white private school on the North Shore.

“My grandmother used to pick cotton during the summer time; now, all of her grandchildren are college graduates. But beyond the degree, my college lacked inclusiveness just as much as it did in the early-70s when my mom was there.”

I suppose it’s ironic when you think about it. Being told you need to work hard to “escape” the only place you’ve called home, just to get to where you’re going and be an outcast of sorts — in your own city, at that.

I discovered the same general concept when talking to entrepreneur, Dan Ware. He’s a former co-owner of Drinkhaus, a Chicago supper club that was once situated not far from downtown in the historically Greek West Loop.

He explained how hard they fought just to get the doors open, weaving through red tape and politics at every turn, and how they were given probationary ordinances as a condition to their grand opening. Now, even with prime real estate and one of the only eateries on the entire block, they still struggle to attract the foot traffic of downtown high-earners and hyper-local patrons they’d hoped to appeal to. Most of their customers come from the South Side, and are Black — which is part of the reason it was so hard to get the building in that space to begin with.

But that’s the way decades of segregation play on a city. It becomes systemic and lives in people’s minds more than their location ever could. Who you are affects where you go just as much as who you aren’t does.

Before I left, he dropped this on me: Go where you're loved.


“Perhaps we are beat down so much from everything that we bond easier over the city itself, and not even our race.”

Christina hit me with maybe the most vivid illustration of why “South Side, Sox Side” means what it does to those that identify with it.

With so much of our success as Black people hinged on our ability to make it out of where we come from, the phrase is a simple reminder that we have a history of success and prosperity right under our noses, ready to be celebrated at any time. This illuminates the reality that living on the South Side of Chicago is, contrary to popular belief, just as much of a choice as it is a circumstance.

So yes, go where you’re loved, and not because you’re afraid to go anywhere else, but because there is no place else you’d rather be.

For a while, Blacks weren’t even allowed to go to Wrigley Field, on the North Side, to see the Cubs play. So it’s no wonder why they’ve taken so kindly to the city’s “other” team that wears black on the South Side, despite them playing in Bridgeport.

“That was one area I was told NOT to go: Bridgeport… and it was always heavy heavy Irish or Italian. ‘You might come up missing’, that’s what you’d hear.”

It’s historically Italian and Irish, and also historically racist, which makes this both ironic, and fitting. In a land where Black people were siloed into specific areas and not given much of a chance to succeed, they have continuously snatched their pride from the jaws of shame.

One neighborhood could never define the South Side, or rob them of one of the few things they’ve captured ownership of.

The truth is that even on the South Side of Chicago, in a land of Sox hats, old covenant maps, and baby grand piano keys, everything doesn’t have to be black and white.


I read something a couple years ago that made me smile: Ida B. Wells was getting a street named after her in downtown Chicago. It’ll be the first one named after a Black woman and run right through South Side’s Bronzeville where a housing complex that bore her name once stood.

Even though I’m not from the city, I think I speak for them when I say it’s about damn time. It will serve as living proof that it’s never too late to go back and reclaim the things you once called your own, no matter how long it’s been.

As for Christina, she’s still undecided on her next move, but she’s got a certain reclamation project of her own in the works.

“Oh, I’m going to start taking piano lessons again very soon.”

Hmm, new apartment, more cocktails, and the baby grand piano? I can’t wait for these dinner parties.

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My thoughts from the worlds of Music, History, Poetry, and Culture. For lack of a wetter bird, I can show you better than I can tell you.

Atlanta, GA

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