How An Old White Guy Got Woke

Dan Wakefield covered the Civil Rights movement, but it took decades to fully appreciate the injustices America inflicts on people of color.

Editor’s Note: In fond remembrance of Dan Wakefield on the occasion of his death, Indianapolis Monthly is revisiting the works of the famed Indianapolis writer, reporter, and prodigal son. The original story was published on our website on June 6, 2019.

Author, Dan Wakefield.

Five years ago, a man called me and began with an apology.

“I’m sure you get too many of these,” he said. “But I have to call you because I am writing a book on the Emmett Till murder trial, and you are the only one who was at the trial and is still alive.”

That has become my distinction.

The Supreme Court had outlawed school segregation in its 1954 decision Brown v. Board of Education, ruling that “separate but equal” education was not valid and no longer the law of the land. Everyone knew this was a major decision that would have a huge impact on American life. There was a feeling of national apprehension. What would happen? Would the South revolt? Would it be the start of another Civil War? It felt like the country was holding its breath.

A year later, in the summer of 1955, newspapers across the country reported the murder of a 14-year-old black boy from Chicago. Emmett Till had gone to visit his great-uncle in Mississippi and was killed for allegedly whistling at a white woman. It was the first big “racial” story that followed the Supreme Court decision, and the trial of the two white men charged with the crime captivated the nation.

I had come to know Murray Kempton, a columnist for The New York Post, and I begged him to find me, then 23 years old, a way to go to Mississippi and write about the trial. My slim credentials at the time included summer reporting jobs at The Indianapolis Star and The Grand Rapids Press. I was an ambitious young journalist, and this trial would be historic. I felt I had to be there. Somehow, Kempton persuaded The Nation magazine to send me. My payment was a round-trip bus ticket from New York City to Sumner, Mississippi. The trip took two days and a night, stopping at every small burg on the way.

Reporters from all over the country had come to the tiny courthouse in the Mississippi Delta. The prosecutor made his case: Till had gone with some other boys to a small store in a town near Sumner. Supposedly, he whistled at or in some way flirted with the woman behind the counter. She complained to her husband, and he and a cousin went to Till’s great-uncle’s house that night and demanded “the boy from Chicago.” Till came out, the two white men took him away, and his body was found a few days later at the bottom of the Tallahatchie River with a 70-pound cotton-gin fan tied around his neck. His face and his body were mutilated, and his mother insisted on an open-casket funeral “so people could see what they did to my boy.”

Wakefield (right) at the Till trial.

The two murderers—they later sold their confessions to Look magazine—sat in the front row, smoking cigars, smiling, yawning. At the end of a week of testimony, the defense attorney announced his faith that “every last Anglo-Saxon one of you men in this jury has the courage to set these men free.” It took the jury a little over an hour to do just that. The first sentence of my article for The Nation, titled “Justice in Sumner,” captured the hopelessness of the decision: “The crowds are gone and this Delta town is back to its silent, solid life that is based on cotton and the proposition that a whole race of men was created to pick it.”

I had no idea then that the story would be the beginning of a writing career and life that often orbited the Civil Rights movement. Over the next decade, I wrote several magazine features on the subject. A few years after the Till trial, I befriended the author James Baldwin, who became the 20th century’s most eloquent voice on the black experience in America. But it wasn’t until I moved back to Indianapolis in 2011 that I finally came to understand how ubiquitous racism remains, and what my experience in Sumner should have taught me long ago.

I first met James Baldwin—Jimmy, as he was known to his friends—in 1957 at The White Horse Tavern, Greenwich Village’s historic literary hangout. Recognizing the author from the photograph on the cover of his Notes of a Native Son, I walked over and introduced myself. The last sentence of his “Autobiographical Notes” in that book had sent a chill of inspiration through me, and I adopted it as my highest and most sacred goal: “I want to be an honest man and a good writer.” I told him I was writing my first book, a journalistic account of Spanish Harlem (Island in the City), and he asked to read it, and invited me to his apartment on Horatio Street for bourbon and Bessie Smith records.

Jimmy knew I had covered the Till murder trial, and he quizzed me about it. He asked what the people in the town felt when the two men they knew were murderers were set free.

“That’s the amazing thing, Jimmy,” I said. “The people in the town were pleased; they thought it was right to let the killers go free.”

Jimmy’s great eyes fixed on me and he said something I will never forget:

“You mean the white people in the town.”

I winced. Of course, I thought. He was teaching me to see more than I was trained to see through the shuttered lens of white perception. He was also an inspiration, continually supporting my work and encouraging me. Once, after he’d returned from a talk at Howard University, he said an old professor there had told him, “When you finish, you got to have a shelf of books, a whole shelf.” He pointed his finger in my direction, and indicated he expected no less from me: “A shelf of books, baby, a whole shelf.”

James Baldwin

After years of friendship, I remember clearly the last time we got together. We were walking uptown on Seventh Avenue from the Village to Chelsea, without umbrellas, as the rain drenched us. Jimmy had been invited by his friend Mary Painter, a prominent economist, to have dinner with a woman she knew who was visiting from France. He asked me to come along. We arrived at Mary’s apartment soaked and chilled, and she quickly got out the bourbon. The French woman—Francine, I’ll call her—was very pleasant and drank along with us. The conversation started out general and light, with plenty of laughter. Then Jimmy began to speak of his younger sister, and his jovial mood quickly darkened. His sister was having a fashion show in Harlem a week later, and her future hopes were wrapped up in it. She was only 16, but she knew the odds were against her as a black girl in Harlem. The leading fashion designers and stylists of the 1950s were all white, the models mostly blond-haired and blue-eyed. There was a “brown bag” standard of beauty in the business: If you were darker than a brown grocery-store bag, you didn’t meet it.

“She is 16 and she is suffering!” Jimmy said.

“Oh, Jimmy,” Francine replied. “All 16-year-old girls suffer. I have a teenage sister myself, and she is suffering, too.”

Stoked with bourbon and wine, I leaped in.

“Teenage boys suffer, too!” I said, thinking self-pityingly of my own adolescent agonies.

“People can only suffer to their own capacity for suffering,” I added, imagining I had come up with some irrefutable gem of human understanding. Only Mary held her tongue that night. Jimmy sat on my left, and he turned his eyes to me with a look of disillusionment and rage. He didn’t raise his voice as he spoke, which made his words even more terrible.

“You don’t understand,” he said.

The table was silent for the rest of the night.

I continued to follow Jimmy on television as he marched with Martin Luther King, confronted Bobby Kennedy, and ultimately moved to the south of France, where he died in 1987. I even reviewed his powerful book The Fire Next Time for The New York Times. But I never called him to try to get together again after that evening at Mary’s. What could I say? I still didn’t understand what had upset my friend so profoundly.

Of all places, Indianapolis seemed like an unlikely place for an awakening. I came back here to live in 2011 after decades in New York, L.A., and Miami—cities with more diverse populations. My friend Kurt Vonnegut once said of Indy, “I grew up in a city as segregated as Biloxi, Mississippi, except for the drinking fountains and the buses.”

My own journey toward that revelation never would have happened had it not been for the annual Spirit & Place Festival. I was asked to give a speech at the event in 2015, when the theme was “Dreams.” After my brief presentation on literary dreams, I stayed to hear a panel discussion on dreams for our city. The panelist whose thoughts I found most interesting was Phyllis Boyd, director of Groundwork Indy, which employs youth to upgrade public spaces. Boyd, a black woman, said her dream was for “a city where everyone can contribute.” My self-referential response was, “Great, ‘everyone’ includes old guys!” 

I introduced myself to Boyd afterward, wanting to connect, to show my appreciation for her work, her effort to reach across the color gap. She had mentioned that her father had gone to Crispus Attucks, so I asked if she had seen the film Something to Cheer About, a documentary about the Crispus Attucks basketball team led by Oscar Robertson that won the state championship two years in a row (1955–1956) and became the first black high school in America to win a state championship in any team sport. (Until 1942, black high schools were prohibited from taking part in events of the Indiana High School Athletic Association.) The city re-routed the Attucks victory parade; after a brief stop at Monument Circle, the usual site of such gatherings, the team was whisked off to celebrate with its fans at a park in one of the city’s black neighborhoods. Robertson left the festivities early, depressed. He went home and told his father, “They don’t want us.”

Boyd said she hadn’t seen it, so I told her I would mail her the DVD. I felt I had done my good deed for race relations.

For Wakefield, meeting community organizer Phyllis Boyd, pictured here, was transformative.

Three weeks later, I was giving a talk on Jack Kerouac at Indy Reads Books, and Boyd showed up in the audience. She thanked me for the documentary, and gave me a gift in return—a book I had been conscientiously avoiding since it had published earlier that year, Between the World and Me, by Ta-Nehisi Coates. A lot of people were comparing it to the work of James Baldwin, which made me feel defensive, as if I were a self-appointed “defender” of Jimmy’s status as the nation’s greatest black author, even though he told me I didn’t understand him.

Because the book had been given to me as a gift, I felt obligated to read it. Between the World and Me is in the form of a letter from Coates to his 15-year-old son, warning him of “the system that makes your body breakable.” He tells his son that, “I am writing you because this was the year you saw Eric Garner choked to death for selling cigarettes; because you know now that Renisha McBride was shot for seeking help, and that John Crawford was shot down for browsing in a department store. And you have seen men in uniform drive by and murder Tamir Rice, a 12-year-old child whom they were oathbound to protect. And you have seen men in the same uniforms pummel Marlene Pinnock, someone’s grandmother, on the side of the road. And you know now, if you did not before, that the police departments of your country have been endowed with the authority to destroy your body.”

Maybe Coates’s words reached me on a level that Baldwin’s hadn’t because by then I, too, had seen the shootings of innocent black men by police on television, over and over. I Googled “How many unarmed black people were killed by police in 2015?” The answer was at least 104, nearly twice each week. I printed the names and pictures of those killed. Rayshaun, Lamontez, Christopher, Junior, Keith, Philandro, DeAngelo, Reginald—names representing recently living and breathing human beings whose skin was darker than mine, whose skin color made them “breakable.”

I thought back to a WFYI documentary called Indy in the ’50s that I had participated in a few years prior. One question asked of all of us who were here in that decade was, “What was it like to go downtown to the Circle when you were in high school?” I talked happily of what fun that was, how much my friends and I enjoyed it. The very next cut was of Robertson, the state’s greatest high school basketball player and one of my heroes, saying, “We were afraid to go downtown.”

I didn’t know. I think of my friends and myself in those days as good, friendly, honest young people. It’s easy to say now, but it’s true: We would have been ashamed to know how our city and its police force discriminated against black people. The evidence was all around us, of course. I graduated in 1950, before Robertson, but I saw his older brother, Bailey, play for Attucks. Those Attucks players were the only black people I saw when I was growing up at the corner of 61st Street and Winthrop Avenue. Sumner, Mississippi, the site of the Emmett Till trial, was no more segregated than Broad Ripple.

In 2016, I was invited to a poetry reading on the south side of the city. Talented poets are plentiful here, but that night it felt as if one of them jumped off the stage and into our heads. Tasha Jones didn’t merely read, but “performed” her poem—her whole body seemed to move and strain in an attempt to make us not only hear but absorb the words of her poem, “From Pyramids to Plantations to Projects to Penitentiaries.”

Jones was also a teacher, and she invited me to visit her class of eighth-grade boys, most of whom are black, at Tindley Preparatory Academy on the northeast side. Jones taught the boys the most appropriate (safest) way to respond if stopped by police—stand straight, hands out of pockets, clearly visible; speak only “Yes, sir” and “No, sir” to questions; if traveling in a group, re-form in twos. These are part of a black American child’s standard curriculum of safety and survival. We are not speaking of black children from Chicago going to the Mississippi Delta in 1955, we are speaking of black children here, now.    

My racial education in Indy continued when I met Aleta Hodge, a fellow former writer for The Shortridge Daily Echo. She had just written a book called Indiana Avenue: Life and Musical Journey from 1915–2015. I first heard of Indiana Avenue as a boy, when I was told—as white boys in our city in those days often were—that Indiana Avenue was a dangerous place where dope-crazed black men would cut the throat of any white person who entered. In the segregated white high schools of my era, it was traditional to “dare” a boy to drive his car down that street with his windows rolled down to see if he could make it through the alleged danger zone alive.

When I learned of this hometown lore as a child in the 1940s, I had no idea that my favorite musical group, The Ink Spots, whose hit record If I Didn’t Care sold 19 million copies, got their start on Indiana Avenue. (One of their original members, Jerry Daniels, taught music at Attucks.) I didn’t know that the strip was a legendary mecca of jazz, and a favorite stop on “The Chitlin Circuit,” the segregated entertainment route that went through Cleveland, Detroit, Indianapolis, Kansas City, Memphis, and New Orleans.

“Many people ask today,” Hodge writes, “‘Why didn’t I know about Indiana Avenue?’ Other cities have aggressively marketed their musical heritage. In fact, the city name is tied to the music such as Kansas City Blues or New Orleans Jazz. However, Indianapolis did not proclaim its musical heritage.”

Businesses on Illinois Street near the Intersection of Ohio Street and Indiana Avenue during the 1950s.

I suspect the reason those who ran this city in the middle of the 20th century wanted to hide that history is because the musicians were black. We’ve now been given five books on Indiana Avenue and its nationally acclaimed music. All five are by African-American writers. Not a single white author I’m aware of has seen fit to cover this fascinating history.

From Hodge’s book, I learned that Noble Sissle, a black man who was born and grew up here, wrote Shuffle Along, the first black musical on Broadway, in 1921, giving singer Paul Robeson and dancer Josephine Baker the first stage roles of their internationally famous careers. The musical was revived on Broadway four years ago and nominated for 10 Tony Awards. Sissle wrote many other musicals and songs, including the national hit “I’m Just Wild About Harry.” Oh yes, he also wrote “The Butler University War Song.” Does his story not belong to the history of this city and state?

Beyond learning about the rich musical tradition of Indiana Avenue, I also found Hodge’s descriptions of everyday black life in Indy enlightening. These nuggets are what white people call “black history.” In reality, it is Indiana history, American history. In a section on the plague of tuberculosis in the early 20th century, a neighbor tells the author’s grandmother, Estella Hodge, about the closing of the only clinic that accepted black patients. The community panics. In another passage, Hodge describes the drainage problems, flooding, and mosquito populations near the White River and Fall Creek during that era. “Due to these inferior conditions,” she writes, “colored people were only allowed to live in this segregated community.”

Segregation has a history as ugly here as in the Deep South. A black family named Greer owned acres of land near 64th Street and Grandview Drive, and according to Hodge, “sold parcels of land to their fellow Attucks alumni. It became a middle-class, suburban neighborhood with the nickname ‘the golden ghetto.’ The homeowners were denied mortgages by local banks, and had to obtain financing from out-of-state companies.” Hodge’s family and their neighbors couldn’t get a mortgage in Indiana. Citizens who had been here for generations had to get mortgages from banks in Colorado.

That kind of discrimination effectively walled off the black population into urban ghettos. “White flight” shifted Indy’s Caucasian population to Carmel, Greenfield, and elsewhere. For the black community, the results were disastrous. My friend Jimmy summed up the phenomenon back in the 1960s: “Real-estate values don’t go down when I move in; they go down when you move out.”

Jimmy, I think I finally get it. I think I’m beginning to understand. I may not be fully “woke,” but at least I am blinking and rubbing my eyes. Absorbing this information about my hometown, these should-have-been-obvious examples of the vast and unceasing injustice this country inflicts on its citizens of color, I look back on your work. What rings most true to me is your story Sonny’s Blues, about a jazz musician. It describes the music of the group as it reaches a peak:

“Creole [the bass player] stepped forward to remind them that what they were playing was the blues. He hit something in all of them, he hit something in me, myself, and the music tightened, and deepened, apprehension began to beat the air. Creole began to tell us what the blues were all about. They were not about anything very new. He and his boys up there were keeping it new, at the risk of ruin, destruction, madness, and death, in order to find new ways to make us listen. For, while the tale of how we suffer and how we are delighted and how we may triumph is never new, it always must be heard.”    

Why did I hear it here when I had missed it so many other places? Maybe the truth learned on the home ground is more real to us. When I witnessed the Till trial all those years ago, I assumed that racism was a regional problem, not a national one. Learning the history of my hometown—that blacks weren’t welcome downtown when I was in high school, that they hadn’t been allowed in tuberculosis centers here or their doctors in our hospitals until 1954—felt personal, not abstract.

In the course of this journey, I realized that when Jimmy lamented his 16-year-old sister’s suffering, he didn’t just mean the barriers she faced as a black woman in a segregated fashion world. He meant the ongoing dangers, handicaps, and injustices that are part of life for African Americans in this country. Not long after our last dinner together, Baldwin was beaten up at an Irish bar in Greenwich Village because he was sitting with two white friends, one of them a blond woman.

Racism is systemic, but grasping the injustice of it is individual. For me, it took listening to Phyllis Boyd talk about her dreams for our city and getting to know her as she drove me around the underserved neighborhoods where she works. It took hearing Tasha Jones perform her poem and observing the lesson she gave her eighth-graders on how to be safe as young black boys today. It took reading Aleta Hodge’s book on Indiana Avenue, and learning not only about my hometown’s great musical heritage, but also about what our local black citizens have suffered. The revelation was not that bigotry once existed in some far-off place, but that it’s a daily terror black people here continue to survive.