Leopold’s FOIA requests also play a role in larger battles for some of the most highly contested documents in the land. In late May, the government decided to release a legal memo about the 2011 “targeted killing” of the U.S. citizen and jihadist cleric Anwar Al-Awlaki, who was killed by a drone in Yemen. A lot of people have demanded to see this memo; the ACLU and The New York Times sued to force its release. The government argued that releasing it would harm national security. But a panel of appeals-court judges ruled that this argument didn’t make sense. Why? One big reason: Leopold already had the memo, in essence. He’d put in a FOIA request for a sixteen-page white paper that contained a lot of the same legal reasoning. It argued that the U.S. could kill a “senior operational leader” or “an associated force” of Al Qaeda without the need for “clear evidence that a specific attack on U.S. persons and interests will take place in the immediate future.”

Leopold’s FOIA successes have allowed him to make a living as a freelancer, writing news stories for Al-Jazeera America, Vice News, and other publications. He also publishes stories at Beacon Reader, a crowdfunding website that lets freelancers sell subscriptions to their work; there he offers “Lessons in FOIA Terrorism,” plus a “FOIA Terrorist” T-shirt, for ninety dollars a year. One reason Leopold has been able to build a following is that he’s a master of the law at a time when a lot of people want to learn it. Unlike many of his disciples, though, he has embraced FOIA for deeply idiosyncratic reasons. He isn’t just using it to dig up documents. He’s using it, in part, to atone for past sins. He’s using it to transform himself.

He’s pretty open about what happened. Writing about Leopold means reckoning with a uniquely full-disclosure human. Early in our conversations, I asked him what a national security reporter was doing in Beverly Hills. Most of those writers live on the East Coast, to be close to government sources. He said he used to live in New York, but he had to get out. Then he told me the story in what seemed like one unbroken breath.

It started with cocaine, which he discovered as a twenty-year-old, working in the music business. As he fell into addiction, a number of bad things happened in quick succession. He failed out of New York University. He tried to kill himself. He spent a month in a mental hospital. He started stealing promotional CDs at the music label he worked for and sold them at record stores to buy coke. He got caught and arrested, and eventually had to plead guilty to a felony theft charge to avoid jail time.

Leopold, at left, and friends gather around the axeman for the metal band Overkill at the old Ritz in New York City. (Courtesy Jason Leopold)

He thought maybe he could get off drugs by moving to a new city, so he left New York for Los Angeles, where he’d met someone on a previous trip—Lisa Brown, a calm, steady woman who worked as a music executive at a children’s TV network. He wanted to marry her. But he didn’t know how he’d make a living. He took stock of his skills. In New York, for a brief time, he’d written obituaries for a small newspaper. “The only thing I knew how to do was write,” he says. So in L.A., he joined the Whittier Daily News as a cops and courts reporter.

His plan to get sober in L.A. didn’t work. Within six months, he was using again. He moved from the paper to a small wire service, which fired him after an attorney threatened to sue for libel over a quote in one of his stories. The quote was legitimate, but the wire service couldn’t afford a lawsuit, and Leopold’s editor didn’t back him.

Not long afterward, in 1997, Lisa, now his wife, confronted Leopold about his drug use. He spent a month in rehab and began to attend 12-step meetings. But he wasn’t in therapy, wasn’t at peace. He spent the next several years chasing stories, winning scoops, and trailing debris through various California newsrooms, never telling anyone about his criminal past. Editors always loved Leopold at the start. He had real talent, an instinct for novelty coupled to an electric aggression, and his stories won lots of internal praise and even some awards. But he tended to bungle quotes and make spelling mistakes, and he was willing to bend or break ethical norms to get stories, sometimes lying to sources to get interviews and breaking agreements he made about what information should be on and off the record. “My whole thing was, I wanted to get at the truth by any means necessary,” he says.

He got fired from the Los Angeles Times after another reporter complained that he was playing music too loud and Leopold threatened to “rip your fucking head off your shoulders, you little prick.” Instead of stepping back, he pushed harder. In 2002, after reporting for a time at Dow Jones Newswires and covering the Enron beat, Leopold published a long investigative piece in Salon about the role of a key Enron figure named Thomas White. Leopold botched it. For one thing, he relied on a particularly damning email from White that he couldn’t prove was authentic. (He says he shared the email with his Salon editors, and they agreed he should use it.) Worse, he plagiarized seven paragraphs of the piece from an earlier Enron story in the Financial Times. Leopold says the plagiarism was a mistake made in haste; he credited the FT in the story, though no amount of credit could have justified that much lifted material. “There’s nothing I can say that will explain it,” he says. “It was completely fucked up.” Salon apologized to its readers, and the media reporter David Carr pointed out Leopold’s mistakes in The New York Times: “Web Article Is Removed; Flaws Cited.”

Leopold revealed all of this in News Junkie, a memoir he published in 2006, with a cover featuring a keyboard, a coffee ring, and a line of coke. News Junkie is a dark book that rides on long passages of dialogue (Leopold says he kept journals) and potboiled prose. Typical sentence: “Hellbent on living the life of a rock star, I drank a half bottle of straight whiskey and snorted eightballs of cocaine nearly every day.” It feels like the outpouring of a guy who realizes he’s been destroyed by the secrets he’s kept and vows to never keep one again. Leopold failed to disclose, so here’s an orgy of disclosure to compensate. He writes that his father, a blue-collar New Yorker with a panther tattoo on his arm, used to beat him. He writes about wanting to smash a particular lawyer’s head with a baseball bat, and deciding to send David Carr a gift-wrapped box of elephant shit, “two big logs,” before losing his nerve. After Carr’s article, Leopold panicked that he would never be able to work in journalism again: “It felt like my arms had been amputated.”

Still, his wife stuck with him. “The thing that I was really drawn to was his honesty,” Lisa says, “which seems so ironic, but he was so real, and honest. He’s very honest with his emotions…. Through the drug-use phase, I still ultimately felt he was honest about how he felt about me. Like, that has never—I have never doubted that.” But if anyone else was going to see what Lisa saw in him, he needed to start over.

One afternoon in L.A., Leopold lets me tag along to a meeting with a source so I can see how he operates now. Leopold’s been talking to the guy for a year, but has never met him in person. The guy says he has some information about misconduct and incompetence in the part of the government that performs background checks on potential employees—the same part that failed to flag Edward Snowden as a security risk. Leopold says he’s asked the source if I can observe their meeting, and the source has agreed.

We walk out Leopold’s front door and hop into his black Mercedes C250. There’s a child seat in the back, and on top of the seat, a stack of rock and punk CDs. (Leopold owns a massive collection of rock-concert T-shirts that takes up almost three full closets in his bedroom and spills into the room proper. “I gave it all up—the drugs, the alcohol,” he says. “I gotta have something.”) I ask how he can afford a Benz. “It’s actually not that expensive,” he says. “Same price as a Prius. My wife drives a Prius.” He pauses. “I’m still fakin’ it, I guess.”

We drive toward Redondo Beach, listening to The Fall and talking about his fascination with Guantánamo Bay. It’s such a strange, dark world, he says, and there aren’t a lot of people reporting on it.

Maybe the biggest story of Leopold’s career came from Guantánamo. Last year, he received an encrypted email from a source. It contained the government’s translation of six handwritten notebooks belonging to a Saudi prisoner named Abu Zubaydah. George W. Bush called Zubaydah “one of the top operatives plotting and planning death and destruction on the United States,” and the CIA used him as a guinea pig for its torture program, flying him overseas and waterboarding him repeatedly. But in a four-part series for Al-Jazeera America, Leopold pointed out that while Zubaydah was clearly a man of “hard-core anti-Western sentiments and a willingness to embrace violence and death for the cause,” he wasn’t the high-level leader the U.S. government had said he was. A functionary, not a mastermind. Leopold used the diaries to humanize Zubaydah. He quoted the jihadist on his fondness for elements of Western culture: “The Lady in Red” songwriter Chris de Burgh; Rambo III (“I watched this movie and I laughed loudly… My eyes became teary because of the deep laugh”); Pepsi (“Five chilled bottles of Pepsi Cola… is a very amazing thing—especially when you drink the bottle as one shot”). “It almost makes me think about myself,” Leopold says. “What made me make the choices that I made in my own life? And is there such a thing as redemption?…. What does it mean, what does it look like?”

Leopold is a jittery driver, checking his phone at every light. He’s afraid he’ll miss something: an email from his lawyer about documents on the way, a note from an editor or a source, a tweet on a breaking story. We eventually come to a coffee shop in a strip mall and get a table outside. A few minutes later, the source shows up and shakes Leopold’s hand. He sees my tape recorder and asks if it’s on; I tell him no. On the other side of the coffee shop’s window, a guy in a Jimi Hendrix shirt is typing on a laptop. “Is he with you?” the source says.

He starts talking at high speed about the nuances of government procedures, jabbing his finger at Leopold’s reporter’s notebook, giving him names and dates but no quotes for the record. Leopold asks a series of simple, basic questions, trying to get the guy to slow down and walk him through the material; the guy asks in a worried tone if Leopold got the documents he sent, irritated that Leopold doesn’t seem to recall every detail. There’s a lot at stake here: If either guy misjudges the other, they could both end up screwed.

Leopold keeps telling the source that he’s okay, that no one is listening to their conversation, but when a random dude in an NPR T-shirt begins to loiter outside the coffee shop behind him, the source clams up until the dude walks away: “He’s wearing an NPR T-shirt.” Leopold is confused by this statement.

After an hour of tense back-and-forth, Leopold shakes the source’s hand and says goodbye, and we climb back into the Benz. Whistleblowers are “a very very unique breed,” he says. He understands and shares their passion for exposing injustice, but at the same time, you “have to really vet them.” The meeting has left Leopold a bit wary. The source’s paranoia, he says, may be a notch against his credibility. It’s hard to know what might be real and what might be generated by the guy’s own fear.

Leopold got burned by a source once. It happened in May 2006, just as News Junkie was rolling off the presses.

Here’s how he tells the story. His phone rang on a Saturday afternoon when he was in the car with Lisa. The call was from an FBI source he trusted implicitly, a guy who had come through for him on multiple stories. Now the source gave Leopold huge news: Karl Rove, the conservative political strategist and deputy White House chief of staff, had been indicted in the Valerie Plame leak investigation.

Plame, an undercover CIA agent, was married to a high-profile former ambassador who had written a New York Times op-ed that angered the Bush administration. Someone with knowledge of her secret identity had leaked it to journalists, apparently as retribution. Leopold felt like this was “the most unbelievable injustice,” and he had been pursuing the story for the liberal news site Truthout. If Rove had truly been indicted, it could reroute American politics. “I was like, ‘Holy fucking shit!’” Leopold recalls. “I pulled over. I was like, ‘Lisa, I gotta go, here, bye.’” Leopold called another source that he and the FBI guy both knew, and the second source confirmed that Rove had been indicted. Next, Leopold called the spokesman for special prosecutor Patrick Fitzgerald and left a message. He didn’t immediately hear back. Then he called his editor, Marc Ash, who interviewed one of Leopold’s sources on the phone “at significant length,” Ash recalls. “I walked away with the impression that I was talking to someone who was in fact qualified, and was providing solid information.”