The Secret to Getting Top-Secret Secrets

How a journalist with a dark past learned to pry info from the government—and redeemed himself in the process

By Jason Fagone
Illustrations by Kristian Hammerstad
Photographs by Chris McPherson

Jason Leopold tells me to pull up a chair in his home office. It’s a weekday morning in March, and he’s working out of his clean, quiet two-bedroom house in Beverly Hills. The office, next to the kitchen, feels like some kind of resonating chamber for his mania, a tiny room with a window that looks out onto a twisty canyon road. A poster of I.F. Stone, the independent journalist and muckraker, hangs on the wall, along with a small, framed piece of paper that Leopold recently found sitting on a table at the U.S. military base in Guantánamo Bay. It’s one of his favorite document scores ever: a “Public Affairs Smart Card” created for the military’s PR folks, telling them to “Own the Interview” and “Stay in your Lane” and listing the many topics they’re not allowed to discuss, including “Investigations or their Results,” “Suicide,” “Construction,” “Presidential Remarks,” and “Attorney Allegations.” (To Leopold, this one scrap of paper made the whole trip worthwhile because it revealed how the government tries to control information. “I’m like, you idiots, why did you leave that lying around?”) And everywhere, stacked on bookshelves and on his desk, are piles of paper from every imaginable government agency, state and federal, topped by response letters: Dear Mr. Leopold… Dear Mr. Leopold…

I first learned about Leopold’s work from Twitter. His profile picture showed him standing in front of the entrance to Guantánamo wearing a T-shirt from the punk band Black Flag. He called himself a “FOIA terrorist”—FOIA, the Freedom of Information Act. I started following him. The range of stuff that zips by on his feed is staggering and kind of thrilling: 140-character dispatches about guards and prisoners, spies and secrets, corporate intrigue, torture and war. Many of his tweets link to government documents he’s dug up. The documents regularly supply ammo to left and libertarian causes (curtailing NSA surveillance, closing Guantánamo), but Leopold doesn’t present as an activist. He comes off more like a stonecutter chipping away at the base of a mountain, sometimes getting pebbles, sometimes boulders.

A single day of FOIA mail for Jason Leopold; like acceptance letters from colleges, the bigger the envelope, the better the news. (Courtesy Jason Leopold)

Today there’s a small stack of recent FOIA responses next to his iMac. When I ask about them, Leopold starts flipping through the pile, page by page, with a mixture of irritation and amusement. He says he asked for all documents from the Department of Homeland Security about how it monitors the Tea Party movement. “This is really frankly fucking annoying as hell,” he says, looking at the letter from the government. The agency took a year to respond to his request, and now it has given him exactly three pages of documents, “redacted to the point where I don’t really know what it’s about,” he says. So he appealed the decision. (He appeals every response as a matter of principle: “I don’t care if they’re like, ‘Here’s a bunch of documents.’ Still appeal. There may be something left. Have them perform another search. Because they’re just terrible at it.”) He asked for all white papers, PowerPoints, and policy summaries on the use of drones in U.S. airspace and internationally for the purposes of engaging in lethal force against terrorist targets. He asked for “all draft talking points prepared by the NSA following the leaks of classified material about NSA surveillance programs”; he already got the final versions of the talking points, but he wants the drafts, too, for insight into the government’s thought process. “This is great,” he says, grinning at the NSA letter. “They identified 156 pages of draft talking points but they classified every single page as top secret.” Leopold shoots me a deadpan look: “The draft talking points.” He asked for all CIA files on the folk singer and activist Pete Seeger. The agency sent him a “Glomar response,” a kind of evasive maneuver in which an agency neither confirms nor denies that the information exists, and says that if it does exist, it’s classified. “Everyone wants to get a Glomar every now and then,” Leopold tells me. “It’s just kind of like: You hit something. You achieved a Glomar: one point!” (Though his request was rejected by the CIA, Leopold obtained Seeger documents from the FBI that show one agent investigating a complaint from a government employee about his “feelings of revulsion” after listening to a “highly inflammatory” Seeger tape.)

Leopold picks up a piece of paper, squints, frowns. It’s a letter from the Postal Inspection Service. He asked them for… something. “To be honest with you, I don’t remember,” he says. “This was not even that long ago. Um.”

We’re not even through half the pile.

The Freedom of Information Act, passed in 1966 to increase trust in government by encouraging transparency, has always been a pain in the ass. You write to an uncaring bureaucracy, you wait for months or years only to be denied or redacted into oblivion, and even if you do get lucky and extract some useful information, the world has already moved on to other topics. But for more and more people in the past few years, FOIA is becoming worth the trouble. There’s a whole segment of the tech community, for example, that wants to improve how cities and governments function by sharing data openly, and sometimes FOIA is the only way to get the right data. Activists are using it to investigate the views and ties of university professors. And journalists are turning to FOIA as the profession changes in ways that make the law more necessary.

For one thing, it’s getting harder for national security reporters to obtain government secrets the old-fashioned way, by coaxing them from sources. Even before Edward Snowden, the Obama administration was pursuing leakers of classified information with unprecedented aggression, going so far as to seize journalists’ phone records. Now, fearing another Snowden, the government has intensified its crackdown. “People are just not willing to give shit up,” Leopold says. “It’s like, ‘I’ll go to jail.’” With FOIA, though, you don’t have to imperil a source: Instead of asking a vulnerable human to spill government secrets, you ask the government for those secrets directly.

There’s also simple opportunism behind the FOIA boomlet in journalism: Primary source documents play well on the Web. They add heft to posts, building trust in young sites. The data work of Nate Silver, the Snowden-sped muckraking of Glenn Greenwald and colleagues, the exposés of Gawker and even TMZ—all of this ravenous digital journalism is trying to tap some external source of truth, to develop some pipeline of facts that can better withstand reader skepticism, and FOIA happens to be a set of pipes that’s already there.

Leopold has shown that it’s possible to build an entire working method around FOIA. Over and over, by demanding information more creatively and more persistently than anyone else, he gets documents no one else gets, like the military’s horrifyingly clinical description of how guards at Guantánamo are force-feeding prisoners on hunger strikes, and manuals describing how the Department of Homeland Security is monitoring Twitter for terrorist threats, and FBI records about the late investigative journalist Michael Hastings. (Leopold got the Hastings records by suing the bureau along with Ryan Shapiro, a friend and fellow FOIA obsessive; the documents showed that the bureau opened a file on Hastings to “memorialize controversial reporting” by him, including a story in Rolling Stone about the American prisoner of war Bowe Bergdahl, captured in 2009 by the Taliban and released in May.)

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.”

Leopold and Ash decided to publish the story without any caveats, without saying it was a rumor. Leopold wrote in Truthout that “Rove’s indictment was imminent.” He was trying to beat the Times and the Washington Post. He did beat them—with a false story. Rove hadn’t been indicted and never would be. In his 2010 memoir, Rove called Leopold “a nut with Internet access.”

The timing, for Leopold, couldn’t have been worse: He had just published a memoir portraying himself as addict, liar, and thief, and now he had blown one of the biggest stories in the country. Other journalists chewed over Leopold’s mistake on blogs, in newspaper columns, and on radio. The Columbia Journalism Review, in an article that still comes up on the first page of Google results for “Jason Leopold,” called Leopold a “serial fabulist” and compared him to Stephen Glass, one of the most prolific liars in modern journalism history. Leopold’s attorney sent CJR a letter saying the statements were false and defamatory: There was a difference between getting a story wrong and making a story up. “I mean, I was a crazy guy,” he says, “but I’m not that crazy.”

Leopold is apologetic and horrified when he talks about the Rove story. “It’s like, what the fuck was I thinking?” he says. Were his sources lying to him? “I really just don’t know.” (Scooter Libby, a close advisor to Vice President Dick Cheney, had discussed Plame with reporters, and was later convicted of four felony counts for lying about it. Rove’s attorney later admitted that Rove had disclosed Plame’s covert identity to a Time reporter but didn’t identify her by name.) The investigative reporter and blogger Marcy Wheeler, who covered the Plame leak and is now known for her work on civil liberties and national security, offers a plausible explanation: “I basically think Leopold got used by FBI sources. He published that Rove was being indicted as a means to pressure Fitzgerald into indicting him, and it didn’t happen, and he didn’t burn his sources, and as a result, he took egg in the face.” Leopold is still trying to figure out what went wrong; earlier this year, he filed FOIAs with the George W. Bush Presidential Library for records on Rove and Plame to see if he could find any clues.

What do you do as a journalist when you run short? The next couple of years were hard for Leopold, and they would have been harder if not for the birth of his son, Hill, in 2008. “I just didn’t care about anything else,” he says.

Despite the perception in some parts of the profession that he was done for, Leopold continued to report. He wanted to make up for the Rove story, and he couldn’t do that without producing new work. He remained on staff at Truthout. He interviewed Valerie Plame on video. (Plame has long supported Leopold; she recently messaged him and one of his Al-Jazeera America colleagues on Twitter and said she was “proud to know you both & call you friends.”) He wrote about veterans and post-traumatic stress disorder for an obscure site. He started his own site and posted the odd document there.

Eventually he caught a break. In 2010, a military source gave him a set of documents he’d obtained through FOIA showing how the Air Force trained young officers in the ethics of launching nuclear weapons. The jewel in the pile was a forty-three-slide PowerPoint presentation in which the Air Force quoted from the Bible (“Jesus Christ is the mighty warrior”), St. Augustine, and Wernher von Braun, the ex-Nazi who helped America launch its space program. (“We wanted to see the world spared another conflict such as Germany had just been through,” the von Braun quote read, “and we felt that only by surrendering such a weapon to people who are guided by the Bible could such an assurance to the world be best secured.”) Leopold wrote a story for Truthout—“Jesus Loves Nukes,” the headline began—and linked to the raw documents in the text. The story spread quickly, shared by readers and by other reporters, maybe because no one sharing it had to worry about whether they could trust the person who had unearthed the documents; they only had to trust the documents themselves.

For Leopold, it was a lightbulb moment; he wanted to do more work with that kind of impact and reach. He asked the military source to help him better understand FOIA, and the source obliged. He explained how to write an effective request. You had to send the request to exactly the right place, and you had to tell the FOIA analyst on the other end which keywords to use and even which databases to search. The trick was to let them know you knew as much about FOIA as they did, if not more.

The great thing about FOIA, for Leopold, was that it didn’t care about his past. It was just a law, an impersonal series of rules and procedures, inputs and outputs. Anyone could make a request: a good person, a bad person, a person who had done something bad and was trying to be good. There was hope in that.

Slowly, letter by letter, Leopold discovered the power of FOIA. The main thing was a simple mental shift, an epiphany that filled him with a glee that never really went away.

According to the law, Leopold could ask the U.S. government for anything, as long as it was an agency record. They didn’t have to give it to him, but he could ask: for emails and schedules and meeting minutes, for reports and standard operating procedures, for PowerPoints and white papers, even for lists of other people’s FOIAs—and not just for these things but also for the things that the government was saying to itself as it decided whether to give him these things. He could ask for the “processing notes” of his own FOIAs. (In one set of processing notes from the Department of Justice, an agency employee jokes that Leopold is part of a “FOIA posse”; a DOJ colleague shoots back that he should start a band.) He could ask for stuff so outlandishly secret and high-level that even he had a hard time believing the government would cough it up, stuff like the emails of Keith Alexander, former director of the NSA—but he got them. This dude who was reading all these other people’s emails? Leopold could get his emails. “Just give them to me! They’re government records, give them to me!” (Leopold recently published emails between Alexander and high-level executives at Google, and the NSA folks have told him that more emails from Alexander are on the way. “The intelligence folks are really nice,” Leopold says. “Even though they’re doing all these allegedly terrible things, they’re really nice.”)

As he investigated the machinery of FOIA, he found the hidden gears and tricks that made the machine work faster. Like expedited processing: If he could demonstrate a “compelling need” for information that must be released urgently, it could move his request to the top of the pile. And at every step, Leopold learned, if the answer was no, he could appeal. Appeal the denial of expedited processing. Appeal the integrity of the search. Appeal the redactions. Sue. Yes, he could sue the government to get the documents he wanted. “Going to court completely changes the process,” Leopold says. “It forces them into action.” With an activist attorney in D.C. named Jeffrey Light, Leopold has sued the government eleven times in the past two years. For perspective, his ten open FOIA lawsuits is nine more than the entire staff of The Wall Street Journal has right now, and it’s about the same number of suits that the The New York Times has opened or concluded in the past year.

“It becomes almost like an addiction, you know?” Leopold says. “It’s not a secret. I have a totally addictive personality. And I think it’s healthy, because I’m taking advantage of the democratic process…. I’m doing everything by the book.” He makes the process transparent, too. He shares not just the documents but the journey toward them. When the government denies him, or heavily redacts, he publishes the government’s explanation, which is often revealing in itself. There’s almost no way for him to lose. Within the FOIA world, anyway. The journalism world is another story.

Leopold is not forgiven. He is followed, he is read, he is respected, and he even has his fans: According to former L.A. Times reporter Terry McDermott, who has written two books about 9/11 and its aftermath, “If [Leopold] were working for the New York Times, every journalist in the country would know who he was.” But because of Leopold’s mistakes on the Rove story, and maybe also the Enron story, he’s still a little bit toxic. I had a hard time getting prominent national security reporters to weigh in on Leopold, even ones who had written about his recent work in a positive light. They’re “sort of caught,” says Allen McDuffee, who covers national security for Wired and used to work with Leopold at Truthout. “They definitely have to recognize the work that he’s done, but they don’t want to give him credit as a journalist for doing it.”

Stories that praise Leopold’s FOIA scoops often refer to him not as a journalist but as an “activist.” Last month, he got into a Twitter exchange with Spencer Ackerman, the national security editor for the Guardian US and a widely respected reporter. Ackerman tweeted, “There is video evidence of Guantánamo Bay force-feedings…. So today, I filed a FOIA for it. We’ll see what they do.” Leopold replied, “Beat u to it. I filed FOIA for it last July & it’s now part of my wide-ranging Gitmo FOIA lawsuit.” Leopold linked to a PDF of his legal complaint. Ackerman tweeted back, “uh, good for you?” Leopold’s whole approach was right there in microcosm, and his problem, too: his pride in being first, his eager self-promotion, his ache for validation from his peers, his peers’ uncertainty about who the fuck this guy is. (In an email to me, Ackerman writes that he and Leopold have “never met, never had any sort of relationship, and so I found it an odd & random thing to tweet at me.”)

(Courtesy Jason Leopold)

Leopold’s crimes against journalism were serious. But it’s hard to think of any journalist who has worked harder to show that he’s changed. Some miscreants don’t visibly change at all and are forgiven anyway. Leopold is different. He’s been sober 17 years, he says. He has made his work part of his rehabilitation; he has slowly rebuilt journalistic trust by circumventing the usual idea of it. “He’s always trying to prove that what people have been saying about him is wrong,” Lisa Leopold says. How many years of good work does he have to produce before he will be forgiven? He already has eight years. So is it ten years? Twenty? Last month, he conducted the first interview in seven years with James Mitchell, the Florida psychologist who helped the CIA design its torture regime and who had never before spoken publicly about his role. Leopold published it in the Guardian, his first byline there. He followed it up on May 22 with his second Guardian piece, based on a classified Pentagon report he won through a FOIA lawsuit; the report described “staggering” and “grave” damage to U.S. intelligence capabilities as a result of the Snowden disclosures, but provided no details of specific damage. Does the fact that he’s writing for the Guardian mean he’s back in the club? No one will tell him; forgiveness doesn’t work like that. Which is why he fantasizes sometimes about The Document.

One day at lunch—a Greek place in Beverly Hills—he tells me he dreams of discovering the ultimate document, some kind of tape or report “where I look at it and it’s like, ‘This is it. This is what I’m waiting for for ten years.” Maybe it’s a videotape of terror suspects being waterboarded by the CIA—a squirreled-away copy of one of the tapes they famously destroyed. Maybe it’s something else. The Document. A record of such clear and deep injustice that it will upend trust in the powerful at the same time it restores trust in him. A thing he can show not just to the public but to the journalism community, to his peers, and say, “Okay, are we good now?”

It’s out there. He may have a filed a request for it a month ago, or a year. And when it suddenly appears, in his mailbox or in his Dropbox, he will know he has to move quickly, carefully but quickly, to push the news into the world before he gets scooped.

This story was written by Jason Fagone, edited by Mike Benoist, fact-checked by Kristen French, and copy-edited by Lawrence Levi. James Tyler contributed research to this story. Illustrations by Kristian Hammerstad. Photographs by Chris McPherson. Contributing designers Carl DeTorres and Luke Shuman. Jack Stewart narrated the audio version.

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