One afternoon in February 2006, federal inmate No. 40948-018, also known as Jonathan Lee Riches, opened his prison mail to find a letter from the U.S. District Court, South Carolina. Riches, then 29, scant of body at five feet ten, 120 pounds, was three years into a 10-year sentence for wire fraud and had petitioned a court to stop his transfer to the Federal Correctional Institution (FCI) Williamsburg, a medium-security prison in South Carolina where, Riches claimed, "named and unnamed" persons were waiting to do him in. The truth was much simpler and less sinister: Riches had been comfortable in his prison in Bennettsville, South Carolina, where he'd made friends with members of a group of antigovernment fraudsters known as the Montana Freemen, and didn't want to move. His petition, which he'd handwritten as a pro se litigant—one who represents himself—and which offered no evidence of his impending doom, was dismissed "for frivolity." News of the unsuccessful appeal had arrived late—Riches had already been transferred to Williamsburg a few weeks earlier—but the letter pushed his agile mind into overdrive. He walked to the prison's law library, sat down at a computer, and logged in to the LexisNexis legal database. The judge had labeled his petition a "frivolous pro se pleading." Just what did that mean?

As Riches watched the computer screen fill with bunk case after bunk case, he noticed one name recurring with remarkable frequency: "Reverend" Clovis Carl Green Jr., a convicted rapist who had bombarded the courts from the 1970s through the 1980s with at least 700 frivolous filings, an unofficial record at the time. If you believe in cosmic forces, or that for every action there is an equal and opposite reaction, this would be the moment when the mechanics of fate (aided by computer algorithms) precipitated an American legal phenomenon. Riches leaned back in his library chair, a dark epiphany taking hold: "I gotta pass this guy."

Over the next few days, Riches hunkered down at the library, and before the week was over he had filed his first suit, in the U.S. District Court for the Eastern District of Pennsylvania, accusing President George W. Bush of being a time traveler who "conspired with Duke of Normandy at Battle of Hastings 1066 A.D. to pervert the English Dictionary and Law." The lawsuit had 900 "codefendants," including the Lady Bird Johnson Wildflower Center, Bumble Bee tuna, and a massive statue that was destroyed more than 2,200 years ago, the Colossus of Rhodes. Riches' suit demanded $379 trillion in damages. Although a judge dismissed the case, Riches found an appreciative audience: The guards at FCI Williamsburg were in stitches over the complaint, and the Philadelphia City Paper published a story on the local boy made bad (Riches grew up in the Philly suburb of West Chester).

This sparked an epic burst of pro se productivity. Hundreds, then thousands, of handwritten lawsuits would follow, along with a roster of self-applied nicknames—Johnny Sue-nami, the Patrick Ewing of Suing, the Crackpot Matlock Judicial Sasquatch—all the products of a rigorous, hyper-focused regimen: Riches would run 10 to 15 miles daily on the prison track, fueling his obsession. "When you're running, the ideas start spinning," he says. "The mind gets more creative. Every day was run, file lawsuits, run, file lawsuits."

In his cell, he'd scour the Wall Street Journal and local periodicals to determine what might garner the most attention in a lawsuit. He identified which federal courts were easiest to work, which motions allowed him to intervene in suits, masquerading as a victim or an attorney, and he learned how to file in forma pauperis, a motion that translates to "in the form of a pauper," to waive fees. He honed what would become his signature style: assaulting a big-name defendant with wacky humor. One in particular, wrote a judge in an opinion, "reads like a cross between Billy Joel's 'We Didn't Start the Fire' and a Dr. Bronner's soap label, if Dr. Bronner had been a first-year law student with untreated paranoid schizophrenia." In August 2007, Riches accused the embattled NFL quarterback Michael Vick of stealing his two pit bulls and turning them into fighting dogs, then selling the dogs on eBay and using the proceeds to buy missiles from Iran. Fox News ran a piece on the absurd suit, rewarding Riches with his first-ever nationwide coverage.