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William Upski Wimsatt

It started with the word nigger. Louis Farrakhan’s son Abnar Jew-baited his high school classmate William Upski Wimsatt, who countered with the N-word. Farrakhan slammed him to the locker room floor. Which got young Wimsatt thinking: How could his love of urban culture—a love that was leading him to graffiti “Jew II” across Chicago—so quickly turn to hate?

Such hypocrisies would force your average dilettante to start looking for another sub-culture to co-opt. Not Wimsatt. Galvanized by loaded questions about race and class that few white people within the hip-hop establishment were asking, Wimsatt began writing incisive, self-critical essays for The Source magazine arguing that white hip-hop heads were guilty of “wanting to be down but not wanting to sacrifice for it—the way blacks have to sacrifice to be down with us.” A year later, at the age of 21, he self-published a manifesto on race, Bomb the Suburbs. The book sold 30,000 copies; Tupac called it the best book he’d read in prison.

In the 12 years since the book was published, Wimsatt has founded four different nonprofit organizations, from the New York–based Active Element, which partners young philanthropists with young activists, to the Philly-based Self-Education Foundation, which has funded homeschoolers, prisoners, and others attempting to educate themselves outside of school.

Wimsatt may seem like a curious choice as a Jewcy radical given that there’s nothing particularly life-threatening, or even ostensibly costly, about his actions. But in a culture in which radicalism has often been reduced to aesthetics, Wimsatt’s insistence on a penetrating self-criticism that leads to real change strikes a defiant pose worthy of recognition.

With his next project, Cool Rich Kids, started in 1999, Wimsatt ingeniously refocused his critical eye from himself to his peers, coaxing would-be bohemians to “come out” about their wealth and inspiring a group notoriously averse to charity to spend more of their money on meaningful causes. “The real test of a radical or a revolutionary,” Christopher Hitchens has written, “is not the willingness to confront the orthodoxy and arrogance of the rulers but the readiness to contest illusions and falsehoods among close friends and allies.”

Wimsatt is now the executive director of the League of Pissed-Off Voters, an organization he helped found after the 2004 election to get young voters involved in local politics. Perhaps the most important thing Wimsatt is showing us is that talk is cheap; if you want to be good, you have to do good.

Next page: Radical economist Hernando de Soto

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