Twain insisted that a visitor always found Chicago a novelty, completely unlike the Chicago from a prior visit: “It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he can make them.” The small town of Chicago (1850 census: 29,963) morphed into a major metropolis in less than two generations (1890 census: 1,099,850).

Despite Chicago’s rapid growth, the city remained an inconsequential place to Twain. In August 1853, Chicago was a train-stop town for Twain on the way to someplace else. After a 26-hour layover in Chicago he hopped a train for the next leg of his trip east to New York.

Chicago’s population boomed later in the century; the city started in 1890 its 94-year run as the nation’s second city, to be overtaken finally by Los Angeles in 1984. But even as an immigrant-rich (40 percent immigrant by 1890), meatpacking and manufacturing industrial powerhouse, Chicago left Twain unimpressed. It remained for him little more than a train-stop town.

Writing as Thomas Jefferson Snodgrass in 1856, he dismissed the city as high-priced hell: “When you feel like tellin a feller to go to the devil—tell him to go to Chicago—it’ll answer every purpose, and is perhaps, a leetle more expensive.” Almost four decades later Twain used a Pudd’nhead Wilson maxim to again deflate the city and its citizens: Satan says, “The trouble with you Chicago people is, that you think you are the best people down here; whereas you are merely the most numerous.”

Twain’s equal as Chicago’s censurer came a century later in the unlikely form of New Yorker writer A. J. Liebling, a disheveled monument to gluttony. His navel peeking through unbuttoned shirts, his gout-ridden walk reduced to a hobble, he proved that a bowling-ball bald, spectacles-wearing, 246-lb. sumo wrestler-shaped man could write like the most celestial of angels about almost anything—the press, war, boxing, food, politics, even Chicago.

Liebling was the first writer, after Twain, whose complete writings I felt I had to collect and read in college. His scarce Second City (I paid $15 in 1962 for a book originally priced at $2) reveled in cataloguing Chicago’s second-class status, based on almost a year in 1949-50 he lived there and a return visit in May 1951. Physically, Chicago struck Liebling not as a great city but as an endless succession of dingy mill-town main streets.

Those who see themselves as Chicago’s leaders flee the city after work to aseptic suburbs like Oak Park to the west and Evanston to the north, he wrote. They leave behind them each evening “the exiguous skyscraper core and the vast, anonymous pulp of the city, plopped down by the lakeside like a piece of waterlogged fruit. Chicago after nightfall is a small city of the rich who have not yet migrated, visitors, and hoodlums, surrounded by a large expanse of juxtaposed dimnesses.”

Liebling echoed Twain as to Chicago’s status as a train-stop town. After World War II, when Robert R. Young, the Chesapeake & Ohio Railway chairman, started a campaign of newspaper ads calling for through passenger trains (“A hog can cross America without changing trains—but YOU can’t”), Liebling interviewed Ernest L. Byfield, a worried partner in several Chicago hotels. “If they ever have through trains, nobody will stop here,” Byfield said.

Chicago lacked excellent newspapers, restaurants, sports teams, and theater. “As a theatrical center, it is outclassed by Oslo, which has a population of four hundred thousand [vs. Chicago’s 3,620,962 in 1950],” Liebling wrote. “It is not considered smart to admit having seen any play in Chicago, because this implies either (a) that you haven’t seen the real play or (b) that you haven’t the airplane fare [for New York] or (c) and possibly worst of all, that you are indifferent to nuances and might, therefore, just as well go back to Fond du Lac, Wisconsin, where you went to high school.”

Liebling admitted that Chicago was first in several categories, but those were its strip-tease joints, gang killings, segregation (immigrant groups as well as races tended “to coagulate geographically”), and corruption. Bob Merriam, an honest, good-government alderman, told Liebling almost proudly, “Chicago is unique. It is the only completely corrupt city in America.” When Liebling responded that he had heard other cities so described, Merriam said defensively, “But they aren’t nearly as big.”

Liebling mocked the University of Chicago as “the only large university that awards a liberal-arts degree for an undergraduate course that starts after the second year of high school and ends after what would anywhere else be the second year of college. As a result of this generous stand, the University of Chicago’s undergraduate college acts as the greatest magnet for neurotic juveniles since the Children’s Crusade.”

A student told Liebling that “the strong point about Chicago is it’s the only university where you can hold a full-time daytime job and still get your B.A. You don’t have to go to class at all. Just read the Great Books and work up a line for the comprehensive examination at the end of the year.” If the university’s next chancellor after Robert Maynard Hutchins should decide to accept candidates out of the third grade instead of the tenth, Liebling says, “he will probably be hailed on the Midway as an even greater educational innovator.”

Liebling’s biographer Raymond Sokolov said Liebling’s outrageousness—his “aggressively classless, democratic style” of writing “that preened itself on its lack of respect for distinctions of high and low”—recalled Twain’s mixing of “sophisticated thoughts and skills with a wisecracking country manner.”

Sokolov described Liebling as “Twain’s mirror image.” Liebling was “a city slicker plunked down in the boondocks…who affected the speech and outlook of an urban street person,” Sokolov wrote. If only Twain and Liebling were present today to take on Chicagoans’ depiction of their hometown as not only a great American city but also a great global city. A 2012 Global Cities Index developed by A. T. Kearney and the Chicago Council on Global Affairs ranks Chicago seventh in the world, ahead of Beijing (14th) and Brussels (9th), Singapore (10th) and Shanghai (21st).

It’s not hard to imagine Liebling and Twain delighting in Chicago’s current status as the U.S. city with the most corruption, the third highest taxes, long commutes and lousy weather—qualities that caused Forbes to feature Chicago in an annual report titled “America’s Most Miserable Cities.” Global city? Liebling and Twain might prefer to label the Windy City a world-class windbag.

Loren Ghiglione

Michael Fosberg did not learn about the truth of his identity until his thirties.

Michael Fosberg plays the race card, literally.

He joked about it as he handed us his business card. “RACE” is emblazoned on the back in big black letters.

The other side listed Fosberg’s contact info and accomplishments: actor, writer, director, teacher and—perhaps the culmination of all of these things—diversity trainer.

We met Fosberg by accident. He led a post-show discussion about race relations after a performance of the Pulitzer prize-winning play Clybourne Park at Chicago’s Steppenwolf Theatre. We invited him to sit down for an interview after we heard his story that night.

Fosberg grew up as a white kid from Waukegan, Ill. While he was living in L.A. in his early thirties, he found out his mother and his step-father—the man who had raised him—were divorcing.

“I realized at this time that I didn’t really know who my biological father was,” Fosberg said. “And here I was losing my stepfather, and I decided perhaps I needed to know some information about [my biological father].”

Fosberg went on a journey to find him. “I knew his name and that 25 years prior to this he lived in the Detroit area—and this was before we used the Internet for everything—I went to the library and they had phone book sections.”

He looked up the Detroit section. “There were six listings and I copied down all the names and numbers,” he said, “and I went home and called the first number on the list, and it was my father.

“And during that phone call, my father proceeded to tell me, as he said, ‘a couple of things you should know I’m sure your mother’s never told you,’ one of which is that he’s African American.”

Fosberg had spent his entire life thinking he was white.

“Well, I was living in an apartment that was about the size of this chair at the time, but I remember being stunned, not so much from the idea of ‘Oh my God, I’m black’ but the idea that—let’s see, this is a big story—I’ve always felt my whole life, I’ve always felt a deep connection to African American people, to African American culture and I never could explain why. And so yes, indeed it was stunning to hear that I was half black, but it was also reassuring that all my life this deep feeling was verified.

“I remember looking across the room I lived in, it was a little apartment, and there was a mirror there, and I was sort of holding the phone, my dad was sort of filling me in on family history, and I kind of glanced over and caught a reflection of myself, and I thought Oh my God, did I just change? Have I gone black and then back to white? It was sort of a surreal experience.”

A lot of Fosberg’s friends weren’t surprised. An old friend called, and Fosberg told him what he had discovered.

“His response was, ‘Damn, I always knew you were black.’ And I was like why did you know that?” Fosberg said. “A lot of my friends had said this. They always had an inkling, and I don’t know, I suppose it’s pretty easy after the fact to say that, but people said, ‘You know, you were so cool, your hair, you had an afro.’”

Although Fosberg was furious with his mother for withholding his identity, his life became richer with the addition of a new family. (He made peace with her).

His unkown family history is indeed rich. He can trace his roots back to slavery. His great-great-grandfather was a member of the 54th regiment of the colored infantry in the Civil War. His grandmother’s father was an all-star pitcher for the Negro Leagues. His grandfather was a genius who started the science and engineering departments at Norfolk University.

For 10 years now, Fosberg has used his story as a springboard for talking to Americans about diversity. He published a book, and he performs his one-man show, “Incognito,” 60 to 70 times a year for schools, colleges, corporations and the government.

In the play, Fosberg discovers his identity at the same time the audience does.

“Some people are kind of disappointed,” he said. “To be frank, white audiences are sometimes more disappointed that I’m not more outraged, perhaps, by the discovery. And I am perplexed by that, because what would I be outraged about? Would being part black be outrageous or bad? I’m confused by that kind of response to it. I was overjoyed. I was like damn. I figured out who I am.”

Fosberg talks about dialogue. A lot, because it’s the key to improving race relations. He sees it in politics, in audiences and in the media. Fosberg said it seems like people want to have this dialogue, but they don’t know how to start it.

“There also seems to be a faction of people who feel like, ‘Oh man, do we have to talk about race?’” he said. “When in fact they haven’t really talked about race. They think they have. And that’s mostly from white people, almost exclusively. And then yes, the dialogue about race is so difficult to have.

“From a white perspective, when you’re in mixed company and you want to have a dialogue about race, white people approach the dialogue from a place of caution, because you want to be careful that you don’t say anything that sounds racist. How can you have open dialogue when you’re coming from a place of caution? You can’t. You can’t be open about it. On the other side of the issue, people of color are ready to pounce on anyone, anything that sounds remotely racist, and so we’re polarized, and we don’t have the dialogue.

“So what I’m suggesting is that we create this space where we can have this dialogue, and it’s not going to be easy, but we have to allow people to say whatever they’re gonna say and not jump on them like they’re a racist. There are definitely, definitely racist things being said all over the place. You see them, you hear them, but rather than jump to calling it racist, why don’t we have some dialogue about it?”

The same thing goes on in mainstream media. Most people are not engaging in the dialogue about diversity.

“I’ve been interviewed by all kinds of media,” Fosberg said. “I’ve been on CNN, All Things Considered, Tavis Smiley Show, blah blah blah,” Fosberg said. “Who has interviewed me to talk about race and identity? People of color. Those are the only people in the media who are talking about it. Why is that?”

The bottom line is that there is no understanding without dialogue, and there is simply not enough dialogue.

Fosberg was a captivating storyteller, and during our interview, he told us about his epiphany at the Inkwell on Martha’s Vineyard, and the man who was moved to tears at his show, and how he forgave his mother for hiding his identity for so long.

But dialogue, dialogue, dialogue. It always came back to dialogue.

A few days later, I struggled to write about our conversation. There was still one question, one that I hadn’t brought up because I thought it might be unprofessional or worse, stupid.

So I pulled out Michael Fosberg’s “RACE” card and called him.

He answered, despite it being well past normal working hours.

“Michael, I have a one more question,” I began. “So I’m a white girl. I don’t know how to start a dialogue about race.

“What questions should I even be asking?”

The difficult part, he said, is that there is an expectation to be an expert, but we don’t know all there is to know about race. No one does.

“Come up front and say, ‘Hey, I want to be honest, this is where I’m coming from,’” he told me. Everyone has a different experience with race.

“It’s up to you to discover and uncover what you know about race.”

He said I asked a good question.

Alyssa

Hyde Park Hair Salon Barber A.C. Chandler shows off his work

Chicago’s Hyde Park Hair Salon, 5234-B South Blackstone, bills itself as the official barbershop of President Barack Obama.

True, the president has been going to the barbershop for at least 20 years (though security now requires a barber to come to him). And in 2009 the barbershop unveiled its President Obama Chair, autographed by the president and protected by a $10,000 clear glass case.

But the barbershop is more than a tourist destination offering pedicures, massages, shoe shines and designed haircuts. It’s history. Started in 1927, the barbershop has served Mayor Harold Washington, Spike Lee, baseball hall of famer Lou Brock and Mohammed Ali, featured in a giant photo on the back wall (Ali got his hair colored as well as cut).

It’s also a place to talk real estate, get free advice about failed romances, debate hot social and political issues and analyze the plight of the Chicago Bears (or any of the other mediocre Chicago sports teams).

Finally, Hyde Park Hair Salon is a place to get a good haircut, whether you are white or black. It reminds me of a day in 1963 when, as a summer intern in Washington, D.C., I accompanied a black friend to a barbershop that informed us it could not—certainly would not—cut his hair. So my friend and I found a black barbershop that cut his hair and mine. But I was scalped.

My barber at Hyde Park Hair Salon was A. C. Chandler, 31, who has been cutting professionally for 7-and-a-half years, 15 years total. His mother, a cosmetologist, “was in the hair world real tough,” Chandler says, “and I guess it rubbed off on me.”

After Thornton Township High School (where he cut students’ hair for $5 to $6) Chandler graduated from Chicago’s McCoy Barber College. There he learned straight-razor shaves and other “old-school methods.”

What is Chandler’s dream? A fan of the travel channel, he sees himself owning his own company and traveling the world to teach barbering. “You get a chance to see how Bangkok is and how Sicily is,” he said.

At the end of my haircut, after declaring he had been running his mouth, he said, “You’re getting the real A. C. Chandler.” And a real haircut too.

Loren Ghiglione

A statue of New York Yankee Joe DiMaggio overlooks Taylor Street in Chicago's Little Italy neighborhood

I kept thinking about race as we walked along Taylor Street in what’s left of Chicago’s Little Italy. Where Italian businesses once stood, LA Tan, Yummy Thai, CousCous and an Irish bar, Drum & Monkey, now thrive.

I recalled our earlier interview in the Missouri town of Hannibal—remember that name—with the local newspaper’s editor who said she had no reporters of color. An Italian-American reporter was as close as she came, she said.

Malcolm X, James Baldwin and other influential activists and writers argued that Italians were not always white. “Well, Hannibal, the most successful general that ever lived, was a black man,” Malcolm X said in in a 1963 interview.

Recalling Hannibal’s conquest of Rome, Malcolm X said: “No Italian will ever jump up in my face and start putting bad mouth on me, because I know his history. I tell him when you talk about me, you’re talking about your pappy, your father. He knows his history, he knows how he got that color.”

Baldwin suggested that Italians arrived in the United States without a sense of America’s color line. Usually they were categorized as white, though parts of the Jim Crow South insisted that, historian Matthew Frye Jacobson writes, “Italians occupied a racial middle ground within the otherwise unforgiving binary caste system of white-over-black.”

So Italian-Americans participated in the lie of white supremacy, Baldwin asserted, escaping the middle ground and learning to demonize black people.

Standing in front of the Taylor Street statue to Joe DiMaggio, I recalled not only the N.Y. Yankee with the 56-game hitting streak and his later life as Mr. Coffee and Mr. Marilyn Monroe, but also his lack of leadership in encouraging black players to enter the majors and join the Yankees.

Did DiMaggio and other Italian-Americans embrace their whiteness, as Baldwin wrote, “because of the necessity of denying the Black presence, and justifying the Black subjugation”? In distancing themselves from blacks, in debasing and defaming blacks, Baldwin concluded “they debased and defamed themselves.”

Loren Ghiglione

Dung Nguyen, director of Community Care Program at the Vietnamese Association of Illinois

It’s easy to miss the hulking brick building on Broadway when you’re in a hurry to get to Argyle, the busy hub of the Vietnamese refugee community in North Chicago. Nicknamed “New Chinatown” by Chicagoans, Argyle offers decidedly non-Chinese fare: steaming bowls of pho, French-style baguettes loaded with Vietnamese flavors, and Viet supermarkets with ingredients to make it all yourself.

We skipped the gastronomical splurge and instead visited the Vietnamese Association of Illinois, situated in a building shyly distanced from the heart of Argyle. Since 1976, the VAI has been serving Vietnamese refugees, who fled their homeland after the Vietnam War (which they, in turn, call the American War).

According to the 2010 Census, nearly 17,000 Vietnamese live in Illinois. The Vietnamese are one of many immigrant groups in Chicago that have created thriving neighborhood enclaves. With the community-building support of the VAI, Argyle has become a part of that success story in just one generation.

Dung Nguyen, bespectacled and wearing a safari vest, looks like a sort of bookish explorer. Nguyen, 68, directs the Community Care Program at the VAI, which assists seniors. A photograph of his younger incarnation as a handsome pilot in the South Vietnamese Air Force looks over his shoulder from its perch on the table behind him. It’s an altar for his proud military past.

Nguyen fought alongside American soldiers on combat missions. For that, he was imprisoned for 10 years after the Communists took Saigon and rebranded it “Ho Chi Minh City.”

He remembers being interviewed by a Saigon journalist shortly before immigrating to the United States in 1992. He was asked where he would most like to live in America.

“Anywhere,” Nguyen said. “Anywhere in the United States, because this is a free country and everywhere it’s the same.” He had no preference for Chicago, Houston or New York. Nguyen just wanted to live in the “dreamland.”

Nguyen was born in Phan Thiet, a coastal town in central Vietnam. At 17, he moved to Saigon to pursue an education in English and American literature. He remembers being particularly fond of Twain, Hemingway and Steinbeck. Twain, he recalls, was his favorite.

Even in Nguyen’s second-floor office, the children playing on the floor below could be heard screaming and laughing. “The afterschool program,” Nguyen explains, shaking his head and smiling at the same time.

When the Vietnamese came to Chicago after the war, their main problem with adjusting to life in America was the language barrier, Nguyen said. Few could speak English as well as Nguyen. Today, he laments the irony that second-generation Vietnamese-Americans are “forgetting Vietnamese” and communicating with one another almost exclusively in English.

To counter this trend, the VAI offers free weekend courses in Vietnamese for children in the community. Nguyen said the non-profit also tries to attract young people with its yearly festivals, the biggest being the Lunar New Year celebration, or Tet, where children are bribed into cultural partaking by small red envelopes (li xi), which are filled with an undisclosed amount of cash.

For all his support of preserving Vietnamese culture, Nguyen is not all that interested in going back to Vietnam. He hasn’t returned once in 19 years. Nguyen says he is skeptical of the government, especially one that would imprison him. He is also reluctant to visit because he has no more friends or family living in Vietnam. “I won’t have anyone to talk to,” Nguyen says.

Outwardly, Nguyen is cheerful and does not play up his harrowing experiences in the war or in prison. He is still very much enamored of literature. In his free time, Nguyen translates French poems into Vietnamese and publishes them in the organization’s monthly magazine. He also cultivates his penchant for travel.

“When I was in school in Vietnam, I studied American literature and we talked about Atlanta in Gone with the Wind. So when I came here, I traveled to Atlanta to have a look.”

Mark Twain, too, traveled around, Nguyen said, zigzagging his finger across an imaginary, unseeable America in front of him. As if we weren’t already painfully aware of that fact, having spent a considerable amount of time crisscrossing the unending plains of the Midwest. He shared a knowing laugh with us fellow travelers.

“Freedom is precious,” Nguyen says matter-of-factly. And that’s why he chooses to stay, knowing all the while that he can pack up at any time and join us on the road.

Dan