It’s a little after nine on a Friday morning. Apparently hip-hop activist William “Upski” Wimsatt forgot I was coming by his Brooklyn apartment. Finally, a short, slightly balding white guy still in boxers and a T-shirt opens the door and lets slide the Yiddish expression of woe, “Oy vey is mir.” This is not what I had expected from the man Cashus D, Universal Ambassador of the Zulu Nation, called “the only down white boy in hip-hop I know.”
But Wimsatt, a 29-year-old native of Chicago’s South Side is all about defying stereotypes. He is perhaps best known for his book Bomb the Suburbs, an unconventional critique of suburban sprawl and socio-economic inequality from an urban, hip-hop perspective.
Bomb the Suburbs, and Wimsatt’s other book, No More Prisons, are a mix of social criticism, political commentary, and autobiography. He tells of being a scribe for the Chicago hip-hop community and covering the local hip-hop scene for The Source at the age of 16, writing graffiti (if you’ve seen “No More Prisons” painted on the sidewalk, Wimsatt is probably the one behind it), walking through America’s worst neighborhoods, and hitchhiking across the country promoting his books and his social agenda.
A common thread running through Wimsatt’s works is the notion that white people should stop isolating themselves from blacks. Instead, he calls on whites to expose themselves to black culture, and work as partners with them for a more just society. Wimsatt also writes about the importance of youth activism as a means of promoting social change, and he touts hip-hop as a catalyst to bring young people together to pursue this goal.
But Wimsatt does not just write about these issues; he is putting his ideas into action. He has co-founded several organizations, including the Self-Education Foundation, which aims to empower people to educate themselves outside the confines of formal educational structures, and Reciprocity, which unites people of diverse racial and economic backgrounds to work on social justice issues.
A few years ago, Wimsatt discovered he would inherit a considerable sum of money, and has begun focusing on philanthropy as a means of promoting social change. “Philanthropy is as exciting to me now as hip-hop was when I was 11,” Wimsatt tells New Voices. As co-founder of the Active Element Foundation and the director of Adventure Philanthropy, he works with young wealthy people (“cool rich kids,” he calls them) to effectively channel their financial resources to support youth activism and effect positive change.
Whether Wimsatt is writing about Chicago b-boys or addressing conferences of “cool rich kids,” a common thread linking his work remains encouraging people to honestly examine their own racial attitudes. He starts with himself on the first page of No More Prisons: “I’m pro-black but I laugh at racist jokes. I’m feminist but I’m a pig. I rarely tell people I’m a Jew. And I’m down with queers but if someone calls me ‘gay’ I’ll say, ‘Fuck you.'”
When I interview Wimsatt in my Brooklyn apartment, he doesn’t seem to have any inhibitions about telling me about his Jewishness. Instead Wimsatt, sporting a green T-shirt with the phrase “Greetings from the Struggle–National Organizers Alliance” emblazoned across the chest, arrives for the interview bubbling with energy. Alternating between sitting Indian style and lying on the carpet, Wimsatt recounts his voyage from his roots in an upper-class intellectual Chicago family to an activist in the hip-hop community.
He begins his story with Hebrew school. There, it dawned on Wimsatt that American Jews were no longer suffering persecution, but that American blacks were. “The real living people who seemed to me like the Jews I was reading about in history were black people in the projects, in the ghettos,” says Wimsatt. “There was a tremendous contradiction in my early mind. We were celebrating our persecuted ancestors and shunning and stigmatizing our persecuted neighbors.”
Along came hip-hop and Wimsatt found his vehicle to learn from and engage with black culture. “This was 1984,” he says. “Breakdancing hit and half of the boys in my private school were suddenly breakdancing for about four months.” I interrupt Wimsatt here to ask if he still breaks. “I can still do a little som’in som’in,” he says and collapses into a handstand on my floor.
After the other boys at his elite private school got tired of breakdancing, Wimsatt was just beginning to venture deeper into hip-hop culture and the black community of Chicago. At the time, hip-hop was a tool to build cultural pride in the black community. Following suit, after leaving his private school for a predominantly black public school, Wimsatt tried to use Judaism as a source of personal cultural pride. He began wearing a Star of David medallion around his neck and, when Wimsatt’s graffiti tag of “Upski” became dangerously infamous with Chicago cops, he changed his tag to “Jew II.” “I remember being like ‘yeah I have a tradition too motherfucker,'” says Wimsatt.
What ended this year-long foray into Judaic hip-hop stylings was a run-in with his classmate Abnar Farrakhan, son of Nation of Islam leader, Minister Louis Farrakhan. In Bomb the Suburbs, Wimsatt relates that one day in the locker room, Farrakhan, “started talking shit about Jews, basically to get a rise out of me. I called him nigger, basically to get a rise out of his father that night at the dinner table. We got in each other’s face and he body-slammed me.” After that experience, Wimsatt tells New Voices, “I think I humbled myself a little bit.” Not only had the younger Farrakhan tossed him to the ground, but Wimsatt also began to reconsider how he was using his Jewishness to relate to American blacks.
You won’t catch Wimsatt wearing a Star of David around his neck anymore. And there’s no “Jew II” scribbled on the sidewalks of New York. Wimsatt realized that he was using Jewish symbols not to celebrate his pride in his vibrant Jewish culture but to prove he could relate to black suffering through the history of Jewish persecution. “The framework of myself as part of an oppressed people or my Jewishness giving me some sort of special connection to black people didn’t fit my actual lived experience,” says Wimsatt. “I really never experienced any disadvantages as a Jew and if anything I feel like I’ve experienced multiple advantages.”
It was a lesson about honest self-examination that laid the groundwork for Wimsatt’s work on race relations. And while Wimsatt now concentrates his energies in philanthropy and promoting causes such as finding alternatives to formal education, youth activism, and prison reform, encouraging white people to examine their role in race relations will always be a foundation for Wimsatt. In No More Prisons Wimsatt recalls a discussion with a black friend who ridiculed his efforts to get white people to talk about race, calling them “white people therapy sessions.” Wimsatt responded: “Fuck what you black people think. The white man got to have Knowledge of Self! That’s the first level of the pyramid!”
