It’s 1999. Congress is battling the urban poor and winning. The War on Drugs is vacuuming young black America into the prison system. The shrinking American city is playing redheaded stepchild to the bustling American suburb. What’s underground hiphop culture’s favorite white ideologue to do?

William Wimsatt, better known to graffiti aficionados as “Upski,” independently published Bomb the Suburbs—a collection of essays that stands as some of the most fascinating reading hiphop has produced—in 1994 at the ripe old age of 21. The smart, self-critical prose of pieces like “In Defense of Wiggers” proved three things: A book can sell more than 20,000 copies with no corporate support; despite publishing-industry gospel to the contrary, young black men do read; and a white person can write intelligently about hiphop without appearing condescending, misinformed, or just plain ridiculous.

After dropping out of Oberlin College, hawking copies of his book while hitchhiking across the country, and moving to the District because “it’s the most fucked-up city in America,” Wimsatt is back in print, branching out, with No More Prisons. In this loosely connected series of articles and interviews, he condemns the bloated prison industry in an attempt to spark a broader discussion about everyone’s latent ability to fix what’s broken in contemporary America. The result is a refreshingly sharp—if sometimes too wide-eyed—vision of “hiphop leadership” that has more to do with Public Enemy’s call to “Fight the Power” than the Wu-Tang Clan’s “C.R.E.A.M.” (“Cash Rules Everything Around Me”). “We need to become politically sophisticated or keep getting our asses kicked,” says Wimsatt of hiphop’s gangsta-rap-fueled ideological crisis. “Our biggest problem is cynicism. I’d like to stir up some energy.”

To this end, Wimsatt’s book reaches out simultaneously to inner-city youth, the affluent suburban kids aping their culture, those rich kids’ parents, and the foundations those parents’ deep pockets support. Running the significant risk of being labeled a sellout to the institutional white world, Wimsatt—a self-described “glue person”—seeks to erect a positive (read: leftist) agenda for both haves and have-nots to rally around. No More Prisons’ fare—ranging from an interview with anti-suburban uberplanner James Howard Kunstler to a discussion of how “cool rich kids” can make a difference with their trust funds—is informative, readable, and infused with the street-level credibility of a man arrested more than 10 times for tagging by age 15.

When not penning the next countercultural phenomenon, Wimsatt shows he’s used his own “Hitchhiker’s Guide to Organizing” (one of No More Prisons’ rants against institutionalized philanthropy) in working with a dizzying array of grass-roots nonprofit groups in Washington and around the country. As a “talent scout” for Shaw-based LISTEN Inc., Wimsatt has dedicated himself to networking with young leaders who can fight the for-profit mentality that has given us the for-profit prison. In pursuit of this formidable agenda, Wimsatt doesn’t ask you to agree with his politics, but simply to sit down at the same table. “It doesn’t matter what I think,” he insists. “I want people to organize around my writing. That’s what gets me up in the morning.” —Justin Moyer

For more information, visit www.nomoreprisons.net.