ESPO, New York
Punishment: Five days of community service.
In 1999, ESPO's house was raided and he was arrested for vandalism and criminal possession of a weapon—a pair of decorative brass knuckles hanging on a wall.
The raid came a day before an event he was throwing with "culture jammer" Joey Skaggs. To protest Mayor Giuliani's blocking of funding for the Sensation exhibition over an elephant-dung-and-porn portrait of the Virgin Mary, they organized an event in Washington Square Park where New Yorkers could hurl wads of dung at ESPO's picture of the mayor for a buck apiece.
Many felt this was a politically motivated arrest, but police said ESPO had been the subject of investigation "for months," presumably because of the number of storefront grates he was painting with his fictional "Exterior Surface Painting Outreach" at the time.
Charged with criminal mischief, ESPO accepted a plea bargain and received five days of community service. He retired from illegal street art the following year.