Excepted from Black in the Middle: An Anthology of the Black Midwest, edited by Terrion L. Williamson. Copyright © Belt Publishing. Excerpted by permission of Belt Publishing. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

Cleveland and Chicago: A Tale of Four Cities

Berlin had a wall. Cleveland has a river.The Cuyahoga River slinks its way northward from about fifty miles southeast of downtown Cleveland, eventually emptying into Lake Erie (Cleveland was founded where the river and lake converge). On its way to the lake, it flows just west of the main part of downtown, through what used to be an industrial area, the Flats, now home to nightclubs and condos. But for years, the river has been like Berlin’s wall to Clevelanders.

The Cuyahoga essentially divides Cleveland into the East Side and the West Side. But the divisions between those two sides aren’t just geographical, dictated by nature’s path. Once you clear the downtown area, the East Side is where the black folk live, and the West Side is where the white folk live. There are exceptions—some white folk live in ethnic neighborhoods on the southern tip of the East Side and the northeastern edge by the lake; there is a long-standing pocket of black folks on the far West Side—but East is essentially black and West is essentially white. It has been this way since everyone I know can remember.

That hasn’t kept black Clevelanders from living full lives. We’ve seldom needed to go any further west than downtown for anything we needed, unless we worked on the other side of town. We’ve always had our own shopping, our own nightlife, our own movie theaters, our own churches, our own parks and playgrounds, even our own public transportation (tellingly, none of the east-west bus lines transverse the entire city, they all end downtown and then go back out where they came from). We’ve had our older neighborhoods where large, sprawling houses still stand, our sturdy working-class neighborhoods, our newer areas where the growing black middle class settled in the ’50s and ’60s, our stretches of poverty and despair. We’ve had our world on the East Side, and most of us presumed whites had theirs on the West Side.

During my youth, no one dared cross town because racism was rampant. Whatever specific incidents that fueled those perceptions had become either distant memories and/or urban legends by the time I came along in the ’60s. Still, no black person risked getting stuck on the West Side for any reason, especially after dark. That was the message ingrained in me by my parents, who were both born and raised in Cleveland. That was the message I carried even while going to an integrated suburban high school—of course, it was an eastern suburb; even the suburbs adhered to the balkanized racial geography.

That racial geography stemmed in large part from the city’s balkanized racial history. There were two different groups of white people to contend with: the old-money gentry, controllers of the business and political arenas and patrons of culture; and European immigrants—Polish, Irish, Italian, Slovakian, German and so on—who assimilated into non-ethnic, all-American whiteness and gained positions of power in the police and fire departments, trade unions, and even the Catholic Church. In their respective ways, neither group made it any easier for the black community, which began to swell in the 1910s as the Great Migration brought impoverished southern blacks northward to Cleveland and other booming Midwestern industrial meccas. Not until the late ’60s was there enough of a critical mass for black people to achieve civic power, with the election of Carl Stokes as mayor in 1967. But none of the black political leadership since then has dislodged the city’s intractable racial divides.

It was not until I returned home after college that I allowed myself the slightest curiosity about the West Side. By then, I’d learned a lot more about the city’s segregated history, and that there were white people on the West Side who were just as keenly aware of it as I was. Feeling more emboldened, I started to (carefully) explore the city past downtown I’d never known. Safer, cultural spots at first—the nightclubs in the Flats, various spots not too far from the West Side Market. It was obvious that economic discrepancies still existed—the stretches of poverty and despair were much less plentiful on the West Side. But as Cleveland’s main economy changed in the late ’80s and ’90s from industrial to professional, with most of the investment happening either in or near downtown or in the area between Cleveland Clinic and University Circle, both sides of town started looking the same to me—which by the ’00s was economically depressed. But the ingrained segregation, I suspect, prevented a lot of folks on either side of the river from seeing that for themselves.

Once, I entertained the thought of moving to the West Side, in search of a cheaper apartment in a less dodgy neighborhood. I had a friend who lived in Tremont, a formerly ethnic neighborhood that started experiencing gentrification in the late ’80s, and thought there might be a spot there for me, in a part of town I’d never before seen. But my parents, well more than set in their ways by then, flatly announced they would never visit me if I moved away from the East Side, so that was that. Indeed, very few people I know of grew up on one side of town and ended up living on the other—and they’re all white.

By the time my family and I moved to Chicago in 2006, Cleveland’s essential segregation just was, economic circumstances be damned. I had no idea growing up segregated would make transitioning to this larger metropolis that much easier.

* * *

A few years after moving to Chicago, there was the Christmastime story of a young black girl who wanted to do something special for her mom. She had occasion to be downtown, amongst its tall, shiny buildings and places of wealth and affluence, and wondered what it would be like for her mom to get to be inside one of them sometime. So, she wrote a letter to Santa Claus asking for a night in a fancy hotel for her mom. Through the auspices of the Chicago Post Office’s “Operation Santa” program, one of those fancy hotels granted that wish.

Something about that heartwarming story struck me as odd. How could anyone not know what those big downtown buildings were like? I’d lived in cities with massive downtowns before—not just Cleveland but also Philadelphia and Atlanta for brief periods—and local features aside, they’re all the same. Awe-inspiring on one level, but no big deal once you’re used to it. Then I learned how some black folks really weren’t used to it, at all. The more I got to know the city, and black Chicagoans, the more I realized how big the chasm here is between engaged and disengaged, rich and poor, black and white.

Across the North Side, where the white folk live, there are numerous post-gentrified neighborhoods, million-dollar condos, fancy restaurants, bespoke retail, numerous food markets, and well-resourced schools. Across the South and West Sides, where the black folk live, there are stretches and stretches where people, property, and commerce used to be, but just emptiness now. Residential and commercial development, if it exists at all, tends to cluster in areas where some level of economic stability already exists, not in the areas that could most immediately use a spark. All is not quite so summarily bleak: there are many spots where long-held neighborhood pride and stability are evident, and many entrepreneurs and organizations are working to establish new community pillars. But the job set out for them is very large, indeed.

This is all the result of Chicago’s notorious segregation and racist housing patterns, which confined the rapidly growing black population to a narrow strip of the South Side as the Great Migration took hold, and then repelled them viciously when they dared expand their horizons. This is the city where Dr. Martin Luther King got an eye-opening taste of northern, big city-style racism back in 1966. Things are better now, if you count that Chicago has elected two black mayors since those days, and was the political seat of Illinois’ two black elected U.S. Senators (one of whom, you may have heard, went on to be president). And there are black people here who have navigated the heights of the business community, and not just Oprah. But the level of civic economic commitments on the South and West Sides is all but invisible, compared to that in downtown and on the North Side.

So why would black folk know their way around the North Side, or even downtown, if their job didn’t take them there? The message that’s been ingrained in black souls here for a century and counting is a simple one: “These places where people have money are not for you. Stay where you belong.” In this construction, Roosevelt Road serves as the de facto line between North Side (and downtown) and the South Side, just as the Cuyahoga divides black from white in Cleveland.

And once I recognized that, the way Chicago is instantly made sense. It’s built largely around the same essential message ingrained in me as a youth in Cleveland. Yes, there is richness and wonder and pride and solidarity in knowing your part of town enjoys a glorious history and ongoing vitality despite its many challenges (both cities can claim black heroes and she-roes in every field of endeavor). But there is also the ever-present danger of self-censoring ambition and mobility, the knowledge that you might be able to conquer the world from your humble ‘hood, but might feel culturally adrift and physically unsafe half an hour away from your house, in merely a different part of the city you call home.

And just like in Cleveland, that sense is fostered here by a long-standing, virtually identical power imbalance between black and white, both politically and economically. Chicago too had rich white fathers who ran commerce and politics and bankrolled high culture, and also generations of European immigrants who laid down the law (and, thanks to Chicago-style patronage, handed out the government jobs). If there are any differences, it might be that racism in Chicago was even more virulent than it was in Cleveland, which might explain why Chicago was not able to elect a black mayor until 1983, well after many major American cities.

In that light, it is no accident that Chicago and Cleveland have historically been two of the most segregated cities in America. It is no accident that the result of that segregation in both cases are cities split in two psychically, cities of self-contained, unequal halves where boundaries are felt and lived, respected if not feared, but seen and surmounted not nearly often enough.

Thus did it become easier to learn my way around my new home, not just logistically but also holistically. Racial divides, sadly, translate rather easily from one locale to the next. But that knowledge didn’t and doesn’t make it any easier to deal with the historic reality of life for black Chicagoans. More than once, as I learned more about the city’s racist history and its lingering vestiges, part of me would wonder why folk didn’t just march downtown and burn the Loop to the ground. Then I’d remember that many of the very same things happened in Cleveland over the years, and no one destroyed that downtown either.

Berlin had a wall, but they took to it with hammers and pick-axes and tore it down. Cleveland and Chicago have walls too, but not the kind you can tear down with a pickaxe. They’ve been erected in places that are harder to reach than a river or a street: bitter, entrenched hearts and minds, both black and white, going back for generations, on either side of town.

Disclaimer: The author used to work for the U.S. Postal Service in Chicago, including the “Operation Santa” program, but not on the specific event discussed here.