Little Brother

Love, Tragedy, and My Search for the Truth


By Ben Westhoff

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This intimate exploration of race and inequality in America tells the story of a journalist’s long-time relationship with his mentee, Jorell Cleveland, through the Big Brothers Big Sisters program and investigates Jorell's tragic fatal shooting.

In 2005, soon after Ben Westhoff moved to St. Louis, he joined the Big Brothers Big Sisters program and was paired with Jorell Cleveland. Ben was twenty-eight, a white college grad from an affluent family. Jorell was eight, one of nine children from a poor, African American family living in nearby Ferguson. But the two instantly connected. Ben and Jorell formed a bond stronger than nearly any other in their lives. When Ben met the woman who'd become his wife, she observed that Ben and Jorell were "a package deal." They were brothers.

In the summer of 2016, Jorell was shot at point blank range in broad daylight in the middle of the street, yet no one was charged in his death. Ben grappled with mourning Jorell, but also with a feeling of responsibility. As Jorell’s mentor, what could he have done differently? As a journalist, he had reported on gang life, interviewed crime kingpins, and even infiltrated drug labs in China. But now, he was investigating the life and death of someone he knew personally and examining what he did and did not know about his friend. Learning the truth about Jorell and the man who killed him required Ben to uncover a heartbreaking cycle of poverty, poor education, drug trafficking, and violence. Little Brother brilliantly combines a deeply personal history with a true-crime narrative that exposes the realities of life in communities like Ferguson all around the country.


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Jorell Cleveland in 2015


I hadn't seen Jorell in a couple months. It was August 2016, and he'd stopped returning my texts. This was a bit frustrating, but I didn't take it personally. After all, he'd turned nineteen that year, and I figured this was typical teenager stuff.

Jorell Cleveland was my little brother. The Big Brothers Big Sisters program had paired us eleven years earlier, and I had watched him grow from a shy kid with a big afro who barely stood as high as my chest to a confident, muscled young man people looked up to. We didn't share blood, but as far as I was concerned he was my family.

Our backgrounds could have hardly been more different. I grew up in a tree-canopied St. Paul neighborhood near the University of Minnesota. My mother was an entomologist and my father a doctor. Jorell lived his early years in a poor Arkansas town, and when we first met, his single-parent father was a roofer raising eight children in St. Louis, Missouri. His mother was in prison, back in Arkansas.

I first moved to St. Louis to attend Washington University. I developed an affinity for the city, and moved back there at age twenty-six for my new job at a weekly paper. Before long I felt a need to get involved in a public service program, one where I could actually make a difference. I read a news story about a Big Brothers Big Sisters program focused on children of incarcerated parents. "For many children, a parent's incarceration often marks the beginning of a generational cycle of crime," the article said. "Having a mother in prison often disrupts a child's environment more than having a father in prison."

The article touched me, and at Big Brothers Big Sisters, they had an immediate, pressing need, particularly for male volunteers. And so after going through a background check I was assigned a match. In the early evening of June 30, 2005, I went to the Big Brothers Big Sisters' offices and met my "Little," a tiny eight-year-old who possessed a gigawatt smile.

"What's your name?" I asked.

"Jorell Marsay Cleveland," he said.

"It's great to meet you," I said, extending my hand.

"Nice to meet you too," he said, shaking it without making eye contact. I thought: There must be some mistake. This kid is so charming and adorable that he couldn't possibly need mentorship. People must fall at his feet. I was also introduced to his father, Joe, who seemed gregarious and appreciative of my efforts.

For our first outing together, Jorell and I ate dinner at an old-fashioned Italian restaurant called Rossino's, where the wait staff melted for him, refilling his 7UP glass continually. He couldn't have been more than fifty pounds.

"Where do you go to school?" I asked.

"Adams," he said.

"Do you like your teacher?"


"What grade are you in?"


It continued like this. He politely answered my questions with one-word answers, an upward inflection on the last syllable. When we said goodbye he asked when I'd pick him up again and suggested, "Monday?" which was that same day.

Jorell craved undivided adult attention. He lived in a crowded household, in a dodgy St. Louis neighborhood called Forest Park Southeast. When I drove through the area at night, guys standing on the side of the street tried to flag me down to sell drugs. One time, when Jorell's dog got off its leash, police shot and killed it.

Despite our biographical differences, we found plenty in common as we explored St. Louis together, trying new burger stands and bowling alleys, and seeing bad movies. I took him to his first Cardinals game at Busch Stadium, and got him swimming lessons at the YMCA.

Jorell could be cripplingly shy, his answers to my questions often barely audible. But he had bright eyes, an insatiable curiosity, and relentless positivity. He liked to feel the stubble on my face with both of his hands. He was game to do anything, even if it was just hanging out by the pool, listening to rap albums, or watching TV in my apartment with my tuxedo cat, Nora.

Not long after we met I went to pick him up at his home, and upon being invited inside was shocked by what I saw. "He sleeps on a bare mattress," I wrote in my journal. "The bedroom door is a frayed blue tarp, and his windows have been broken but never replaced." But Jorell almost never complained. One time he found a Books-A-Million gift card in his backyard, and I took him to the mall to redeem it, but the card had no value. Later, his bike was stolen. Still he didn't get angry or rant about unfairness. He just accepted life as it was. He never wanted to discuss his mother in prison, or any other hardships. I didn't press him.

A year into our pairing, Jorell told me that his family was moving to a new house in the St. Louis suburb of Ferguson. This was a chance for them to get away from the violence and poverty of their city neighborhood. I visited when they moved in, and I was surprised by the size of their six-bedroom home. The backyard was as big as a football field. This was late 2006, the go-go era for real estate, and Jorell's dad also invested in another house in the area, which he rented out.

This seemed to be a step up for the Cleveland family. Though I didn't know much about Ferguson, a municipality of twenty-one thousand people, I had middle-class friends who'd been raised in that part of the metro area, known as North County. It was the suburbs, so it had to be safer than the city, right? As I looked around, I saw an area in flux. Some houses on the block were run down, others well maintained. A cute downtown business district was just a short walk away.

Most of the Clevelands' neighbors were white, but, as I would later learn, Ferguson's population was changing quickly. In the years leading up to Black teenager Michael Brown's killing by a white police officer in 2014, the city would become majority Black for the first time, even as the power structure—the lawmakers, the police, the school board—remained white.

It was all part of the evolving demographics of North County, which includes dozens of small towns north of St. Louis. Black families (like the Clevelands) were arriving from the city, while white families were fleeing for suburbs even more distant.

"What do you think?" Jorell asked, showing off his bedroom. I took stock: its only piece of furniture was a blow-up bed, which he shared with three siblings. But the possibilities were endless.

"It's awesome," I said.


As a staff writer at the local weekly, the Riverfront Times, I wrote about everything from news to sports to restaurants. But my primary beat was hip-hop music, which was blowing up in St. Louis thanks to the success of multiplatinum rapper Nelly, famous for his song "Hot In Herre." Rap music was also the soundtrack to Jorell's life and a big part of how we connected. We listened to CDs together and shared notes on albums. Jorell introduced me to new rappers, and I wowed him with stories of interviewing artists whose songs he loved.

Many found it amusing that I, a straightlaced white guy, covered hip-hop, especially considering I neither looked nor acted the part. But it was the music I loved. Plus, it was a great topic for a journalist, as it wielded enormous cultural influence. Rock stars tend to be boringly middle class, but the rappers I interviewed often had cinematic, rags-to-riches stories. Very few journalists were telling their stories, and covering hip-hop gave me a chance to meet people from different backgrounds, as well as an entrée to parts of St. Louis I never would have known otherwise.

Nonetheless, by 2007 St. Louis started feeling small. I wanted to advance my career as a writer and decided the best place to do that was New York City. I rented a small apartment in Brooklyn, and began hustling up freelance gigs.

Jorell and I stayed in touch, and we spoke on the phone regularly. I soon began spending time with a woman named Anna, eventually moving in with her in Hoboken, New Jersey. In 2008 ten-year-old Jorell boarded a plane for the first time in his life to visit us for a long weekend. "He enjoyed the flight, watching the cars on the ground turn to ants and drinking Sprite," I wrote in my journal.

He and Anna got along well. We looked out from the top of the Empire State Building. We explored art galleries in Chelsea. He tried sushi for the first time. He wanted to buy an oversized, novelty $100 bill at a tourist shop, but I talked him out of it. The next summer he came back and stayed with us for five weeks, sleeping on the couch in our duplex and attending a YMCA day camp. Jorell quickly made friends with the other kids in the neighborhood, and even started a dog-walking business with the boy next door, posting signs around the neighborhood.

In these years I saw Jorell searching for an identity, not unlike young people anywhere. One time he sported an afro; the next time cornrows; the next time, his head was shaved. Kids made fun of him at school because of how small he was, and he sometimes got into fights. But I never saw that, and he didn't want to talk about the tougher parts of his life. He often relied on small scowls or pursed smiles to express his emotions, except in those rare situations where he felt completely comfortable, when he would explode with waves of roaring laughter.

During a visit to the Museum of Natural History on his first trip to New York, I snapped a photo of him standing next to a tiger, stuffed and roaring in a glass cage. Jorell posed with his hands up in the air, cowering and pretending to be petrified of the tiger. When I look at the photo now, I see the ideal image of childhood: a happy boy, carefree, totally at ease, unguarded.


In 2014 I moved back to St. Louis yet again, this time with Anna and our two young boys. Anna had never lived there, but I'd gone to college at Washington University and worked at the Riverfront Times. We moved to be closer to our families; plus, Jorell lived there, and we were thrilled to reconnect.

But upon our October 2014 arrival, St. Louis was in flames. It was the 250th anniversary of the city's founding, but no one was celebrating. Just two months earlier, Michael Brown had been shot dead in Ferguson. Images of Brown's body in the street went viral, and local businesses were burned to the ground. Jorell joined the protests and looting on Ferguson's main thoroughfare. A Justice Department report later detailed how the Ferguson police department targeted African Americans.

Brown's killing shook me because in him I saw Jorell. Michael Brown was only a year older and he lived nearby. They were acquaintances; Jorell could have been him.

During this time I wanted more than ever to be there for Jorell, and through early 2016 I saw him regularly, hanging out and tutoring him with his classwork. But by that summer, when he was nineteen, he'd grown increasingly difficult to reach. He didn't have a phone of his own, so I had to go through his dad, his sister Iesha, or his girlfriend Danielle. They usually told me he was busy. He had just returned for his fifth year of high school, and spent long hours frying chicken at his job.

When we did get together I often smelled marijuana on him, and his energy level varied wildly. Sometimes he was practically lifeless, barely listening when I talked and falling asleep in my car. Other times he bounced with uncharacteristic pep. Though I worried there were things he wasn't telling me, I figured he probably wasn't up to anything more scandalous than I'd done at that age.

Plus, I was busy too. That summer I prepared for the release of my third book, Original Gangstas, a history of Los Angeles gangsta rap in the 1980s and 1990s, as well as the LA riots, gangs, police brutality, and crack epidemic that also defined the era. I got to talk to my West Coast childhood heroes, guys like Snoop Dogg, Dr. Dre, and Ice Cube. Jorell was excited about the book. Though he tended to prefer newer rappers, I'd gotten him into the old West Coast stuff, particularly Snoop Dogg, who was a wiry, menacing Long Beach Crip when he was young. It was striking how much Jorell resembled him, right down to the wispy mustache.

I was working on my book promotion on a Saturday afternoon in August 2016, when I received a phone call from a number I didn't recognize.

"Hello, Ben? Are you sitting down?"

"Who is this?"

"This is Danielle's mother."

This woman—the mother of Jorell's girlfriend—was someone I'd never spoken with in my life.

"What happened?"

"Jorell has been shot," she said. "He's dead."


After Jorell's death I went numb. I remained so through his funeral, which was attended by dozens of friends and family members, and for weeks to come. I had no idea why he was killed, and it appeared that the police didn't either.

Weeks turned into months, and my shock turned to anger. As the killer continued to go unnamed, that anger turned to guilt. Without knowing why he was killed, I focused the blame on myself. To this day the guilt hasn't subsided. I was his Big Brother, after all. The Big Brothers Big Sisters program had no specific requirements for the program—it was our bond that kept us together for over a decade, not any formal obligations—but I believed it was my job to keep him safe. And at that I failed.

One thing seemed certain: his shooting must have been random. The killer must have mistaken him for another person, or he must have accidentally gotten in the middle of someone else's dispute. He was so good-hearted he couldn't possibly be tied up in any dangerous business. There was no denying that he had a lot going against him in his life, but he had a big heart and a winning attitude, and didn't seem to possess an ounce of cynicism.

Who could possibly want him dead?

That's the question I set out to answer in this book. Doing so required me to find out what was happening behind the scenes in his life—the stuff he never told me. It required me to reconstruct his last months and speak with almost everyone he knew well.

When the police investigation into his death stalled, leaving Jorell's family desperate for answers, I took matters into my own hands, employing my skill set as an investigative journalist to find the truth. I retraced his steps through dangerous North County streets, tracked down underworld figures, and pored over reams of police records.

In the end, what I discovered challenged almost everything I believed about Jorell. It turns out he wasn't the happy-go-lucky kid I'd always believed he was. He'd grown paranoid in his final months, answering his front door while clutching his gun. He also had real enemies I never imagined.

This story is much more than a whodunnit. Seeking the truth about Jorell's killer required me to understand the troubled history of St. Louis, how discrimination and pervasive poverty has shaped life for millions. It also required me to examine my own choices and mistakes.

I conducted this investigation for Jorell's family and friends and for myself, to help those who knew him heal. But I held in mind those who live on the margins, whose deaths are seen as insignificant. St. Louis now experiences more violent crime than any other major American city. As measured by per capita homicides per year, it's thirteenth in the world—with the top twelve all located in Mexico, Venezuela, and Brazil.

We process these deaths through ninety-second news clips, if at all. But there's a lifetime of pain behind each killing. Mothers who lose their children, and then lose themselves. Kids who never learn to trust again after their fathers are taken.

I wanted to know what was causing so many homicides. And I wanted to understand something we all know exists but rarely interrogate ourselves: Why can't people in places like Ferguson live in peace?

As a reporter, I had investigated other homicides, but Jorell's death happened so close to home that I failed to see the full scope for some time. Going after criminals wasn't new to me, but doing so had never felt so personal, or presented such challenges to my family. I considered the potential repercussions for my wife and children, chasing an at-large suspect who had killed and could kill again. But I just couldn't let it go. Jorell's family needed to know who did this, and so did I.

There were times I was terrified, and considered abandoning this quest altogether. But ultimately this book became the most rewarding project I've ever taken on. Because, though it's a story of tragedy, it's also one of hope. My research taught me more about Jorell than I'd known during his life, and it helped me understand what made him such a remarkable kid. It brought me closer to his family, and closer to my own.

Investigating Jorell's death also helped me understand the dual worlds that exist in all cities: how wealthy people rarely cross paths with those living in poverty amidst violence. It helped me see, with my own eyes, the inequalities I'd taken for granted. I learned about the systems that conspired against Jorell, and how they might be torn down.

Part I

Chapter One

I grew up near the University of Minnesota's St. Paul campus, an area where, legend has it, you can throw a rock in any direction and hit a PhD. My dad's medical clinic was close; my mom's lab was even closer. At the local hardware store, just behind the gas station, I earned $4.25 an hour cutting glass to replace broken windows and helping old-timers with their home-improvement projects. My best friend, Eric, lived literally across the street. His parents didn't mind when I barged right in without knocking.

The high school I attended with my siblings, St. Paul Central, was located in a mostly Black neighborhood. We attended as part of a unique desegregation program, with white students from other districts bused in for an advanced curriculum called International Baccalaureate. As a freshman I found the place intimidating. From the outside, Central resembled a prison, and, during school hours, kept its doors locked with electromagnets. Inside, the bottom two floors housed the "regular" classes, while the advanced, mostly white classes were on the top two floors. The annual coronation to crown a homecoming king and queen usually pitted Black candidates versus white candidates, and you could count on plenty of booing in the crowded gym.

This was the early '90s, and my friends and I appropriated our identities from Black culture coming out of South Los Angeles: The Chronic, Boyz n the Hood, Menace II Society. We'd drive to the Mall of America in Eric's minivan, bumping Snoop Dogg's Doggystyle and trying (and failing) to pick up girls. After practicing tennis on our school's dilapidated courts, my teammates and I would use fake IDs to buy forty-ounce bottles of Olde English 800, and then pick up bathroom tissue multipacks. We'd put on Eazy-E, drink, and blanket the trees of our rivals' homes with toilet paper.

My adolescence was full of small rebellions. I once took a date to the local zoo—after hours, hopping the fence when it was closed. My teenage friends and I roamed the neighborhood at night, bored, sometimes breaking into unlocked parked cars and stealing their CDs. We devised elaborate schemes to get out of paying bills in restaurants. In high school I skipped Spanish almost every day, and instead I'd go out to grab fast food with my friends and occasionally get drunk. Despite this I got into a good college, with all the assumed ease people of my world expected, ready to start the next stage of my life.


My family is half WASPs, half scrappy European immigrants.

My grandmother's Orthodox Jewish family arrived a hundred years ago from Romania to Lower East Side tenements. After falling in love with a Christian man originally from Germany—my Grandpa Richard—Grandma Doris ran away from home. Some family members never spoke to her again, and her marriage with my grandfather didn't work out too well either. They had a messy divorce, and Grandpa Richard basically kidnapped my dad when he was thirteen and took him to Europe for a year.

My mom's family includes Mayflower descendants. Her dad, Grandpa Shelly, was short and bald, but a baller in the academic world, a celebrated University of Minnesota genetics professor who invented the discipline known as genetic counseling. He advised the Pope and appeared in hundreds of newspaper stories. Grandma Elizabeth was a talented biologist, but, due to the sexist norms of the time, was not permitted to be a professor at the university because her husband was one.

My mom skipped her senior year in high school to enroll at Cornell University, where she met my dad in the choir. Neither could sing much, but they began dating and attended an ROTC ball together. It's funny to see that picture, with my mom in a ball gown and my dad's hair shorn short, considering my dad soon abandoned his military training as their hippie instincts kicked in. My mom stopped shaving her legs and helped organize grape pickers with Cesar Chavez in California. After college she taught English for two years in Ghana. My father avoided Vietnam by volunteering in the VISTA program, where he taught GED classes in Mason City, Iowa.

He became an occupational medicine doctor, and my mother an entomologist, studying bugs. In our home's basement she kept an aquarium crawling with long, creepy, South American cockroaches. Their shelves held Bob Dylan; Joan Baez; Free to Be You and Me; Our Bodies, Ourselves; and Earth First! journals.

For my brother, sister, and me, public service was a critical part of our upbringing. My mom's parents opened their home to Hmong refugees, and when Grandpa Shelly retired he taught Hmong children how to write their language. My mom tutored a Vietnamese refugee named Quang for years; he'd fled his country by boat, forced to leave his wife and two small boys behind. We built houses with Habitat for Humanity, and in high school I organized a volunteer program at a Minneapolis soup kitchen. We attended summer solstice celebrations, called Pagan Parties; vacationed in foreign countries; and ventured into deep wilderness for camping trips. Even as my dad drew a doctor's salary, he bought his clothes from Goodwill and volunteered at a co-op grocery store so hardcore that it didn't sell chocolate or coffee.

Rejecting the conservative establishment was paramount, my parents taught me. Getting a corporate job and a McMansion was a fate comparable to death.


The summer after eighth grade, my church confirmation class journeyed five hundred miles south to St. Louis for a service trip.

The twenty members of this coed group wore ozone-depleting hair products and roamed the humid metro area in a state of high hormones. There was making out, petty rivalries, and anguished breakdowns. I can't think of greater torture for our youth minister and parental chaperone. We visited the famous inverted catenary made of Pennsylvania stainless steel (aka the Gateway Arch), and then the Budweiser brewery, where we got free soda and hard pretzels. We also volunteered at a day camp in the city, and at night slept on the floor of a church in the suburbs.

Four years later, as I considered colleges, I returned to St. Louis to visit Washington University. I'd chosen the right weekend, as one of my favorite rap groups, The Pharcyde, performed a free show in the quad for a bash called WILD, which stands for Walk In Lay Down theater. Frat guys lugged over couches and kegs for the occasion, and somehow this university-sanctioned event permitted underage students to get nauseous on warm Natural Light beer and Jell-O shots.

My college choice now cemented, my dad deposited me in my dorm that fall. I still knew very little about St. Louis. A snobby East Coast floormate decried the local cultural offerings and called our new home state "Misery." His roommate sold me a quarter ounce of marijuana for $35, which turned out to be mostly sticks and seeds.

The school's campus offered the full elite college experience, with collegiate gothic architecture and luxurious lawns in every direction. "This is like heaven," Jorell said when he visited with me years later. He had been born in Arkansas during my sophomore year, and would move to St. Louis as a kid. But in college I had absolutely no idea how the other half lived. I rarely traversed into the city other than for subpar Italian meals at The Old Spaghetti Factory. Instead I stayed on campus, started a humor magazine, and tried to read Infinite Jest.


  • An A-List Editor's Choice selection from St. Louis Magazine
  • St. Louis Post-Dispatch Top Nonfiction Book of 2022
  • "The creative and original telling of a young man’s life and death on the streets and the Big Brother who sought his killer.”—Sam Quinones, author Dreamland
  • "Important and a must-read."—Gerald Early, The Common Reader
  • “Westhoff’s new book, Little Brother: Love, Tragedy, and My Search for the Truth, is a memoir, a double bildungsroman, and a murder mystery. By combining these forms, it goes deeper than any one of them could…. The book opens a navigable passage between their separate worlds, and it goes below the surface characterizations, the stereotypes and assumptions that kill any honest discussion….Little Brother also makes a subtler point: that it is possible for two people to love each other across worldviews that do not sync. Jorell’s life is as exhausting and dangerous as any double agent’s. The details Westhoff uncovered teach us about his home terrain, about the geopolitics of isolation, about realpolitik and the limitations of allies.

    “If a reporter had parachuted into this story, it would have ended up a flat, remote, predictable account of one more young Black man’s death. But because Westhoff lived it, because he cared, he lets us wonder and puzzle and rage along with him.”

    The Los Angeles Review of Books
  • "I finished Little Brother in one day. It humanizes people and communities who have long been dehumanized. So much of it hits close to home. Ben Westhoff has taken a lot of crazy risks in his work before, but it’s the emotional exploration here that makes it his bravest work yet.”—Aisha Sultan, St. Louis Post-Dispatch columnist
  • "Briskly paced...gritty,...[and] personal."—New York Journal of Books
  • "With Little Brother, Ben Westhoff takes a relentless journalistic approach to discovering truths about a personal tragedy. Masterful."—Toriano Porter, Kansas City Star editorial board member and author of The Pride of Park Avenue
  • “Meaningful memoir…Author and journalist Ben Westhoff’s investigation into the murder of his Big Brothers Big Sisters mentee, Jorell Cleveland, is not only a deeply personal, emotional memoir, but it’s also one of the best examinations of the systemic issues that lead to the deaths of so many young men in North County.”—St. Louis Magazine
  • "A very good narrative by a very good author."—Tyler Cowen, economist
  • “Thought-provoking…[an] ultimately satisfying study in true crime.”—Kirkus Reviews
  • “The death of a young Black man begets a thought-provoking…account from journalist [Ben] Westhoff…showcasing his investigative chops."—Publishers Weekly
  • “Westhoff’s...most personal book yet explores the multilayered communal aspects of grief, justice, and loss as he investigates the murder of Jorell Cleveland…. A heartfelt account of a life cut short, and the jarring inequities that contributed to the tragedy."—Library Journal

On Sale
May 24, 2022
Page Count
288 pages
Hachette Books

Ben Westhoff

About the Author

Ben Westhoff writes about culture, drugs, and poverty. His books are taught nationwide and have been translated around the world. He is the author of Original Gangstas, the definitive history of West Coast hip-hop, and Fentanyl, Inc., the bombshell first book about fentanyl, and now speaks at opioid conferences across the country. He is the Executive Editor of Euclid Media Group and lives in St. Louis, Missouri, with his wife and two children.

Learn more about this author