How Grammy Winner Rhymefest Sacrificed Fame to Help Chicago Kids

Chicago has become an urban abstraction, a point of reference in discussions about race, violence and policing. People outside the city want to know what is going on here. Donald Trump propelled himself to victory in November in part by yammering about “the African-Americans” and “the Latinos” “living in hell” in “war-torn” Chicago. The city admits to paying out more than $660 million to deal with police misconduct during the past dozen years. Chicago’s body count for 2016 has reached 678 killed and more than 3,700 shot, in absolute numbers more than in any other U.S. city. Trump’s presidency will likely do Chicago’s most vulnerable more harm than good. But Rhymefest puts it in a historical context: “Black people may not have as much of a hard time with Trump as president,” he says, “because we’ve already been living as an oppressed people. Our parents and grandparents, who have seen worse, know the country will keep on going.”

Chicago’s violence is largely isolated to a few black neighborhoods on the city’s South and West Sides. And the reasons for it can seem paralyzing in their depth and -complexity: the fragmenting of major gangs into hundreds of leaderless cliques; the proliferation of guns, many coming from across the Indiana border; low police morale as well as a distrust of the police in the most affected areas; and the long-term effects of segregation, disinvestment and depopulation. “Chicago doesn’t have a violence problem. We have a problem of lack of economic opportunity and a problem of systemic inequality,” says City Treasurer Kurt Summers. “Headlines about violence ignore the root cause of how we got here.”

As the city reels, Chicago hip-hop artists have been pursuing solutions and demanding justice. In late September, Chance the Rapper hosted his sold-out Magnificent Coloring Day Festival on the South Side, with the NAACP registering voters and Chance using the occasion to launch SocialWorks, his nonprofit focused on Chicago youth. During the same weekend, a few miles away, Common’s Common Ground Foundation and Donda’s House — the community group run by Rhymefest — produced their own event, Aahh! Fest. The organizations gave away thousands of free tickets to young people to hear music and learn about job and education opportunities. Lupe Fiasco’s nonprofit was on hand promoting healthy food initiatives.

Because the city has dynamic arts organizations like Young Chicago Authors, there has also been a great deal of overlap between emerging hip-hop acts and black activists leading protests on the streets. In late October, rapper Vic Mensa timed the release of a video for “16 Shots,” a searing song about the killing of 17-year-old Laquan McDonald by a Chicago police officer, to coincide with a rally that he attended on the second anniversary of the teenager’s shooting.

Rhymefest is not newly political. In 2011, he ran for alderman of his South Side ward, losing to the incumbent in a runoff. His opponent, a former police officer named Willie Cochran, dismissed him as a gangbanger and rapper who was perpetrating “one of the biggest attempted frauds that there is or has ever been in Chicago politics.” For the past three years, Rhymefest and Donnie Smith, his wife of six years, have operated the nonprofit Donda’s House (named for Kanye West’s late mother) that uses the arts to improve the lives of young Chicagoans. “People are like, ‘I make it to escape it,’” Rhymefest tells me. “My whole thing is, I make it to rebuild it.”

Right now, Rhymefest is at a fascinating crossroads. His dual paths in music and community work have often seemed frustratingly at odds. That he has stayed on the South Side (unlike his more successful peers) was a source of pride as well as consternation. He yearned to be a more accomplished artist, in part so he could afford to do more for people in his hometown, but also because he had dedicated his life to hip-hop and needed to believe in his talents. It was nearly impossible to find the time to do both well. Then he went through the robbery and the incident at the police station. He was inspired. His funk lifted. Within two days, he released a new song, “Cops N Robbers.” Over the recording of his maddening exchange with the police, he raps: “Cop looking at me not giving a f—/Stuffing -cookies in her mouth, playing Candy Crush/Lost my respect and the public’s trust/Why I really don’t talk to police that much.” It’s no wonder Chicago police report clearing only one-fifth of their murder cases, less than one-third of the national average, and why people in these neighborhoods feel like they have to deal with threats on their own.

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Beyond the music, Rhymefest wants to help people across the divides in Chicago to talk and share and heal. He has called for citywide therapy sessions and a broader focus on professional standards. “White people look at the police like they own them,” he says. “It’s the position we have to come from: ‘I’m your employer, you are a civil servant.’” And because the city is at loose ends and has been made a national spectacle, people downtown are no longer writing him off as a gangster. They want to hear from a rapper who speaks for his community and comes with solutions. Since the robbery, Rhymefest has appeared on TV and met with the chief of police, major foundations and Mayor Rahm Emanuel. It feels suddenly like his roles as hip-hop artist and community activist are fusing, feeding each other, forging what looks, maybe, to be a model for a new kind of career.

“I’m a rapper who is a mix of conscious and street,” says Rhymefest, as if trying on the idea. “Once I figured that out, I had to figure out my product. I’m selling community restoration. I’m selling an idea of how to be involved in the community and do music and be an artist.”

Back in December 2015, in the weeks after the release of a videotape showing the Chicago police officer firing 16 shots into McDonald, Emanuel gave a major speech. The video was withheld from the public for 10 months, and in response to charges of a cover-up, the mayor declared that a code of silence existed within his police department and promised changes. A task force he appointed found that “C.P.D.’s own data gives validity to the belief the police have no regard for the sanctity of life when it comes to people of color.”

Emanuel walked a fine line, however, between further alienating officers and pushing for reforms. The Department of Justice’s civil-rights division launched an investigation into the CPD, and young black activists were demonstrating in the streets and commandeering public meetings, calling for greater accountability and even the abolition of the force.

Then the first nine months of 2016 proved to be the deadliest in Chicago in a generation. On Sept. 22, Emanuel delivered another speech, one he called the biggest of his career, on gun violence. He had focus groups listen to early drafts in which he concentrated on absentee fathers and personal responsibility. (Barack Obama was criticized at times during his presidency for a similar focus when discussing the problems facing black communities in Chicago and elsewhere.) But he was persuaded to emphasize jobs instead — according to a Great Cities Institute report, more young black men are unemployed in Chicago than in any other city in the country. In his address, the mayor promised both to add police officers and to invest in mentoring programs for the city’s youth.

The September speech, at Malcolm X College, two miles west of City Hall, was by invitation only. (No way were protestors disrupting this talk.) The mayor asked Rhymefest to sit in the front row and referenced him in his remarks, juxtaposing Rhymefest’s video at the police station with another one showing activists taunting cops. “Respect is a two-way street,” announced Emanuel.

When the mayor finished, politicians, several of whom were surely looking ahead to the next election, grasped Rhymefest’s hand in two of theirs, telling him they really appreciated how he framed these issues. A former Gangster Disciples strongman who had helped orchestrate a gang truce back in the 1990s asked him if they could meet, and Cochran, his old election foe who was now under federal investigation for misusing campaign funds, greeted him as if they were best friends. Every local news outlet corralled him for an interview.

Rhymefest wore a black leather jacket, a salmon-colored shirt and, I noticed, Superman socks. He wished Emanuel hadn’t called out gangbangers as irredeemable, he said on camera. Like many black men in these neighborhoods, he too had a criminal past. Did Emanuel think him beyond redemption? Rhymefest said all of Chicago — white, black and Hispanic (each group makes up roughly a third of the population) — needed to see that they had a stake in solving the crisis. Violence was increasing in some gentrified areas, and the city's national reputation was affecting everyone. “It’s not a South Side or a thug or a gang problem,” he said. “We have a systems problem.”

Summers — who, with the mayor’s support, has proposed running a $100 million fund out of his treasurer’s office to invest in the Chicago neighborhoods most in need — echoes this idea. “No amount of police officers or detectives is going to change the economic conditions for people in deep poverty on the South and West Sides of the city,” he said. “It can’t be done without real investment in the neighborhoods.” When an interviewer asked Rhymefest if Emanuel’s big speech had met his expectations, he shook his head. “Expectations can’t be met in a speech. The only way to meet expectations is when you see a reduction of crime. It’s on the streets.”

“Did it feel to you that all eyes were on me?” Rhymefest later asks me. “I don’t know my political relevance in the city,” he says. “But I have a feeling that whatever it is we do, whether it’s with Donda’s House or with a healing -project, it’s got to be good, and it’s got to be serious. People are watching.”

Rhymefest grew up poor, without a father or much of a family structure. “My situation wasn’t like Common, Chance or Kanye” -- South Side rappers who came from more stable, middle-class homes. “It was closer to Chief Keef, more in line with a Chicago trap artist,” he says. His mother had him in 1977, when she was 15. They remain close, but during his early years she was more peer than parent, and Rhymefest bounced around the South Side, dropping out of high school in 10th grade. He always had a knack for turning the world around him into rhymes, and he was concerned from a young age with issues of social justice. “He was an old soul, bothered by unfairness and the imbalance in the economy,” says Konee Rok, a music video director from Chicago who started filming Rhymefest when they were both teenagers attending local hip-hop parties. “He wanted to show people they could do better for themselves — that’s always been true.” When Rhymefest and West met at these parties, the 15-year-olds connected over music. “There was magic between them,” says Rok. Even then, they were like Steve Wozniak and Steve Jobs: Rhymefest, the wordsmith, bringing the raw material; West, the beat-maker and producer, able to take the humor and substance from the lyrics and figure out how best to present them.

Rhymefest first made his name as a battle rapper, stalking stages across the country, defeating Eminem and a host of others. He had a son, married and divorced. In 2005, he was MC’ing for Mark Ronson’s DJ sets when he won the Grammy for his part in writing West’s “Jesus Walks,” a top 20 Billboard Hot 100 hit. At 28, he believed, he was set to be a star, signing what he said was a $2 million deal with J Records. Most rappers boast about a street-cred past while flaunting the Cristal-sipping come-up. Blue Collar, Rhymefest’s 2006 album, was clever and catchy, but the subject matter was all struggle, Chicago hip-hop by way of Raymond Carver, with rent checks overdue and women in bars lamenting their dashed dreams. The album sold fewer than 70,000 copies, according to Nielsen Music. “My life has been a series of great failures,” says Rhymefest now.

A year later, he and West landed a deal to write a pilot for Comedy Central: Alligator Boots, a sketch comedy show with puppets. They worked on it for a year at the Jim Henson studios in Hollywood. Rhymefest voiced the show’s host, a rapping pig named Pork Troy. “Comedy Central saw it and was like, ‘No,’ ” says Rhymefest. The pilot never aired. He drifted after that, unsure of his next move, watching the careers of friends like West flourish.

While living in Yonkers, N.Y., Rhymefest met his now-wife, Donnie Smith, online, their talk of forming a new freedom movement turning romantic. He had had a second child, a daughter, with another woman by then, and Donnie persuaded him to return to Chicago, where his children were. In 2009, he went to Hawaii to help write West’s My Beautiful Dark Twisted Fantasy, and with the money he earned he self-financed a second album, El Che. “I wish it would disappear,” he says now, explaining, “It’s hard to do music without people around you can trust. Without them, you’re an amateur.”

The foreclosure crisis had hit by then, with two-thirds of the city’s vacant homes pooled in black and Latino neighborhoods. Rhymefest wanted to do something about the empty houses and the absence of grocery stores and jobs and hope, so he ran for alderman. But the lengthy political campaign bankrupted him. By the end of it, he and Donnie couldn’t pay their rent. They lost their car. Rhymefest fell into a depression and his sugar levels spiked, almost sending him into a diabetic coma. West happened to phone then, flying Rhymefest to Paris to work with him on Yeezus. He made enough to purchase his father’s childhood home.

The two-story house is in a part of the Chatham neighborhood where handpainted block-club signs mark the end of many streets. Rhymefest’s awards sit on the mantel, and on the day I visit, a dog built like a 4-H prize-winning pig nuzzles my leg for attention. “I bought this house for my kids, as the -inheritance that I never got,” says Rhymefest. But his 18-year-old son and 9-year-old daughter are currently staying with their mothers, and he worries that with his changed life as a rapper and activist, he hasn’t had time to be a good father. “You hope your kids can grow up and forgive,” he says — recognizing that he might be repeating a line his own father said in the documentary.

West officially sits on the board of Donda’s House, but it’s essentially a two-person operation run by Rhymefest and Donnie. Donda West, who died in 2007 of heart failure after cosmetic surgery, was a Ph.D., a Fulbright scholar, an expert on Russian poetry and the chair of the English department at Chicago State University. Rhymefest used to call her Miss Maya, for Maya Angelou. He relates how one time when he was making a song in her house with her son, rapping about the drugs he sold, the girls he slept with, the suckers he had shot, she pulled him aside. “Did you really sell all that dope, shoot all those people and have sex with all those young women?” she asked. Nah, Rhymefest, then 16, admitted — he just wanted to get on the radio. “Can you live in that lie you just told?” she asked, pressing him to talk about his family, his hopes for his sister. “That’s the best song you never wrote.”

“She activated who I am now,” says Rhymefest. “It was like she touched my forehead and brought the light out.” And that’s what he wants to bestow on the students of Donda’s House, even if it means foregoing opportunities to write hits elsewhere.

“Che is an alien; he’s very unique,” rapper Xzibit says of his friend. “He’s not choosing to play the same game as everyone else. When you give of yourself and do things in your community, that’s not a paycheck. That’s not a glorified position. Teachers get that kind of attention, not rappers.”

During the past two months, Rhymefest’s days have taken a turn for the surreal, shuttling him between makeshift recording studios in South Side basements and conference rooms in office towers. He hosted a vigil against gun violence, and as a “hip-hop humanitarian” lectured at college campuses. He performed in Washington, D.C., at the opening of the Smithsonian’s new National Museum of African American History and Culture, and he spent an afternoon at a photo shoot after Chicago magazine made him one of its “Chicagoans of the year.”

The Rev. Jesse Jackson recently recorded a song, “Mastermind,” with Rhymefest and Common. Talking about it, he invokes the musicians who helped power the struggle for civil rights. “In the heat of the rebellion zone, Aretha singing ‘Respect’ — how much that meant to us,” he remembers. Jackson reminds me that few people took seriously the idea of a Martin Luther King Jr. federal holiday before Stevie Wonder released “Happy Birthday” in 1980, and “the thing took off in the wind, the culture blowing it across the country.” Rhymefest, says the reverend, “is doing that in this inner-city crisis, using that tradition of artist, activist and change agent.”

One Thursday, Rhymefest meets Jeff Townes, better known as DJ Jazzy Jeff, in the lobby of a North Side hotel. They head upstairs with two of Jeff’s associates, and a white couple steps aside to cede the elevators to them. “It’s OK, we’ll take the next one,” jokes Rhymefest, imitating the couple once the doors close. “That one guy has dreadlocks. We’ll wait. This is Chicago.” 

Jeff and Rhymefest have a band called Jeff N Fess. “Mr. Officer,” a song they released for free in October, sounds like Marvin Gaye’s “What’s Going On” updated for the Black Lives Matter present, with Eric Roberson singing the hook and Rhymefest rapping that his taxes pay police salaries and buy their uniforms. “Fest is such a visual writer. He can write funny, or he can write Kanye’s most personal pieces, or ‘Glory,’ moving into social issues,” says Jeff. “It’s almost a natural progression that once he realized he has that power, why not use it to try to make change.”

In the hotel, Rhymefest launches into a favorite theme: “Genius is never you. It’s your collaboration. People don’t talk about The Famous Flames around James Brown or The Wailers,” he says. “The problem with rappers is they try to go at it alone. My mission is to teach rappers how to collaborate.” Rhymefest now feels confident, sure he’ll succeed in his current ventures, because he has the right collaborators around him. A super squad. “Wu-Tang!” he shouts. “The Avengers!” cries Jeff.

Jeff N Fess cut a song for Marvel’s Black Panther, the comic written by National Book Award winner Ta-Nehisi Coates. Rhymefest plays it — an old-school hip-hop action soundtrack, with Fess sounding as aggressive as early LL Cool J — as he drives Donnie and me to his next meeting, passing through the posh neighborhoods just north and west of the Loop; he mutters about a guy jookin on a busy corner, twisting his body into ringed shapes: “Come on, man, act normal.” In 2015, Rhymefest modeled in a “real-life hero” themed Kenneth Cole ad campaign, and on the way to a popular diner called Little Goat, he says, “Every deal I do has to have a community component.”

After releasing “Cops N Robbers,” Rhymefest decided he wanted to lead an effort that would transform how Chicagoans imagined one another. He proposed a post-apartheid South Africa–style truth-and-reconciliation effort. Everyone in the city, he reasons, is suffering from trauma after decades of gun violence, police misconduct and segregation. He envisions volunteer therapists on hand at multiple sites across the city, their sessions broadcast live.

Angelique Power, the president of one of the city’s major nonprofits, The Field Foundation of Illinois, says she had been talking with colleagues about the need for just such an effort, launched not by people in downtown offices but by an influential person from the community. Then she heard what Rhymefest was doing and joined the advisory committee he was assembling. “Coming off his experiences, he could be leading an entirely different movement, but this one is based in compassion and healing,” says Power. “The fact that he wants to use his energy on behalf of the city makes it seem like we might actually be able to do something very important.”

At the diner, we squeeze into a booth with another member of the truth-and-reconciliation advisory committee, Rev. Dr. Beth Brown of Lincoln Park Presbyterian Church. She leads a mostly white and wealthy congregation, and both she and Rhymefest are eager to combine forces. She mentions that her church uses “compassion cards,” a crowd-sourcing tool, to help victims of gun violence. “Hold on, I got it,” Rhymefest calls out, his hand raised to still the table. “After the citywide therapy sessions — boom! — the compassion cards go up on the website. Instead of you trying to do this on your own, we do it together.”

Walking to his car later, Rhymefest plays with the conversation, testing its lyrical potential: “I was talking to this pastor in a purple shirt. What if you had a card to bail you out. A compassion card.” He turns to me, smiling. “The music is always happening. What’s happening now is a unique experience.”

Rhymefest doesn’t want to discuss Kanye West but can’t help but bring him up. They last spoke in December 2015, when Rhymefest visited Los Angeles. “He had some bad people around, giving him advice,” he says. “I’m concerned about his mental well-being. He’s pulled in multiple directions.” He told West that Chicago needed him, certainly more than the fashion world or reality TV did. And, he contends, West needs his hometown. “Kanye used to be trying to find humanity through his vanity,” says Rhymefest. He references lines he loves from “All Falls Down,” which West raps in his Chicago twang: “I got a problem with spending before I get it/We all self-conscious, I’m just the first to admit it.” But, says Rhymefest, “the vanity has won. So whatever.”

Downtown on a Friday evening, Rhymefest lugs a 25-pound speaker to the free songwriting seminar he’s giving to 20 Donda’s House students. Even with all the accolades of the past weeks, he’s still struggling with money issues and the choices he has made. The pressing work he feels compelled to do means showing up for three-hour classes on nights like this one, reaching only a few students at a time. He bristles thinking about rappers he knows who are selling out tour dates and landing roles in TV shows and movies. He says he expects his “quarterly depression that artists go through” to return. “No matter what I thought, whatever Kanye did, it worked. ‘You’re the icon, you’re the genius,’ ” he says. “Here I am, carrying this speaker.”

The class is the first of a series of 10, and the students, all of them African-American and between the ages of 18 and 24, begin, a little shyly, introducing themselves by their stage names — Rise and B Good and God’s Poetic Child and Pixel and Mosaic and The Honorable Hakim Do. Rio, who sometimes goes by Gotti, says there is a fresh bullet hole in his front door and that a friend of his was killed two days earlier. He fears for his two little brothers. “I’ll call you Rio,” says Rhymefest. “We’ve already got some Gottis.” Then he tells Rio to take care of himself first, otherwise he might never be able to help anyone else: “I want you to be an artist and a dope human being.”

It’s no surprise that Rhymefest is a great teacher. He commands the tiny stage of the classroom, prowling the space inside a rectangle of tables. He corrects students on their posture and pacing as they perform, breaking into song himself. Students write biographical verses, and Rhymefest compliments, prods and jokes. He shares his own experiences in the industry, mistakes and all. In the spirit of Donda West, he implores the young men and women to tell stories unique to their own experiences. “Do you got to say, ‘Hands up, don’t shoot’? If it’s not your story, don’t say it. If your story is trap, be trap. If it’s drill, be drill.”

Not long ago, the media and music executives were fixated on drill, a Chicago subset of hip-hop distinguished by gang-beef lyrics and embodied by rappers like Chief Keef, who became infamous in 2012 after a rival he was warring with on social media was gunned down. But Chance the Rapper has emerged as the new face of Chicago rap — speaking to the city’s realities but remaining hopeful, spiritual, fun. Rhymefest found that his students still identified as much with drill rappers like Keef or Lil Durk as with Chance or Vic Mensa, and he says he has no problem with violent subject matter. He only demands that the songs rise to the level of art. He cites a drug-dealing song by the revered Houston rapper Scarface as an example. “He feels as vulnerable as the crackhead he’s dealing the dope to,” says Rhymefest. “He’s giving the full story.”

During the next several weeks, Rhymefest raves about the songwriting classes he has taught. He brought in a voice coach and had Malik Yusef, the spoken-word artist, talk at one of the seminars. In November, he and Donnie were able to purchase Donda West’s onetime home in the South Shore neighborhood — the house Kanye grew up in — to serve as the headquarters of Donda’s House. Rhymefest says he dreams of buying entire blocks, providing stable homes and jobs for Donda’s House students.

“This is what I live for,” Rhymefest tells me. “I love these kids.” But he immediately contradicts himself. “I can’t be 50 and training 19-year-olds about rap. I might not even like rap then. I need to train my replacement.” Trump’s victory, he says, has inspired him. His students were fearful, believing their world was falling apart. But they got busy exercising, reading history, throwing themselves into music. Protestors filled the streets of downtown Chicago. “Their consciousness level is raised,” says Rhymefest. “If there was ever going to be a time for a conscious rapper, it’s now.” His work has never been more relevant — “I was ahead of my time, and now I’m right on the post” — but it’s bigger than him. “This is the beginning of the rebuilding of our community.”

A version of this article originally appeared in the Nov. 26 issue of Billboard.