Even without the vegetable headwear, Marlinspike’s wire-thin 6’2″ frame and topknot of blond dreadlocks doesn’t fit the usual profile of the crypto world’s spooks and academ­ics, nor RSA’s corporate types. Walking toward the ball­room where he’s set to speak on the annual Cryptographers’ Panel, however, he tells me it’s not his first time at the conference.

In fact, when Marlinspike made his debut visit to RSA 20 years ago, as a teenager, he wasn’t invited. Lured by the promise of seeing his cryptographer heroes in person, he snuck in, somehow snagging a confer­ence badge without paying the $1,000 registration fee. Later, he made the mistake of handing it off to friends who were more interested in scoring lunch than in hearing about pseudo-random-­number generators. They were spotted and kicked out. RSA organizers must have gone so far as to report Marlinspike’s mischief to law enforcement, he says; years later he requested his FBI file and discovered a reference to the incident.

A middle-aged man in a sports coat and jeans approaches us, carrying a Wall Street Journal. He shakes Marlin­spike’s hand and thanks him for creating the encrypted messaging app Signal, which the man says was recommended to him by a friend, a former FBI agent. Marlinspike looks back at me with raised eyebrows.

Signal, widely considered the most secure and easiest-to-use free encrypted messaging and voice-calling app, is the reason he’s been invited to speak as part of the very same crypto Jedi Council he had worshipped as a teenager. Marlinspike designed Signal to bring uncrackable encryp­tion to regular ­people. And though he hadn’t yet revealed it at the time of the conference in March, Signal’s encryption protocol had been integrated into WhatsApp, the world’s most popular messaging app, with over a billion users.

“I think law enforce­ment should be difficult. And it should actually be possible to break the law.”

For any cypherpunk with an FBI file, it’s already an interesting morning. At the very moment the Cryptographers’ Panel takes the stage, Apple and the FBI are at the height of a six-week battle, arguing in front of the House Judiciary Commit­tee over the FBI’s demand that Apple help it access an encrypted ­iPhone 5c owned by San Bernardino killer Syed Rizwan Farook. Before that hearing ends, Apple’s general counsel will argue that doing so would set a dangerous legal precedent, inviting foreign govern­ments to make similar demands, and that the crypto-cracking software could be co-opted by criminals or spies.

The standoff quickly becomes the topic of the RSA panel, and Marlinspike waits politely for his turn to speak. Then he makes a far simpler and more radical argument than any advanced by Apple: Perhaps law enforcement shouldn’t be omniscient. “They already have a tremendous amount of information,” he tells the packed ballroom. He points out that the FBI had accessed Farook’s call logs as well as an older phone backup. “What the FBI seems to be saying is that we need this because we might be missing something. Obliquely, they’re asking us to take steps toward a world where that isn’t possible. And I don’t know if that’s the world we want to live in.”

Marlinspike follows this remark with a statement that practically no one else in the privacy community is willing to make in public: that yes, people will use encryption to do illegal things. And that may just be the whole point. “I actually think that law enforcement should be difficult,” Marlinspike says, looking calmly out at the crowd. “And I think it should actually be possible to break the law.”

OVER THE PAST several years, Marlinspike has quietly positioned himself at the front lines of a quarter-century-long war between advocates of encryption and law enforcement. Since the first strong encryption tools became publicly available in the early ’90s, the government has warned of the threat posed by “going dark”—that such software would cripple American police departments and intelligence agencies, allowing terrorists and organized criminals to operate with impunity. In 1993 it unsuccessfully tried to implement a backdoor system called the Clipper Chip to get around encryption. In 2013, Edward Snowden’s leaks revealed that the NSA had secretly sabotaged a widely used crypto standard in the mid- 2000s and that since 2007 the agency had been ingesting a smorgasbord of tech firms’ data with and without their cooperation. Apple’s battle with the FBI over Farook’s iPhone destroyed any pretense of a truce.

As the crypto war once again intensifies, Signal and its core protocol have emerged as darlings of the privacy community. Johns Hopkins computer science professor Matthew Green recalls that the first time he audited Marlinspike’s code, he was so impressed that he “literally discovered a line of drool running down my face.”

Marlinspike has enabled the largest end-to-end encrypted communications network in history.

While Marlinspike may present himself as an eccentric outsider, his ability to write freakishly secure software has aligned him with some of the tech industry’s biggest companies. For a time he led Twitter’s security team. His deal with WhatsApp means that the Facebook-owned company now uses his tools to encrypt every message, image, video, and voice call that travels over its global network; in effect Marlinspike has enabled the largest end-to-end encrypted communications network in history, transmitting more texts than every phone company in the world combined. In May, Google revealed that it too would integrate Signal—into the incognito mode of its messaging app Allo. And last month, Facebook Messenger began its own rollout of the protocol in an encryption feature called “secret conversations,” which promises to bring Signal to hundreds of millions more users. “The entire world is making this the standard for encrypted messaging,” Green says.

So far, governments aren’t having much luck pushing back. In March, Brazilian police briefly jailed a Facebook exec after WhatsApp failed to comply with a surveillance order in a drug investigation. The same month, The New York Timesrevealed that WhatsApp had received a wiretap order from the US Justice Department. The company couldn’t have complied in either case, even if it wanted to. Marlin­spike’s crypto is designed to scramble communications in such a way that no one but the people on either end of the conversation can decrypt them (see sidebar). “Moxie has brought us a world-class, state-of-the-art, end-to-end encryption system,” WhatsApp cofounder Brian Acton says. “I want to emphasize: world-class.”

For Marlinspike, a failed wiretap can mean a small victory. A few days after Snowden’s first leaks, Marlin­spike posted an essay to his blog titled “We Should All Have Something to Hide,” emphasizing that privacy allows people to experi­ment with lawbreaking as a precursor for social progress. “Imagine if there were an alternate dystopian reality where law enforcement was 100 percent effective, such that any potential offenders knew they would be immediately identified, apprehended, and jailed,” he wrote. “How could people have decided that marijuana should be legal, if nobody had ever used it? How could states decide that same-sex marriage should be permitted?”

To some, Marlinspike’s logic isn’t quite as airtight as his code. Not all criminals are tech masterminds.

He admits that dangerous criminals and terrorists may use apps like Signal and WhatsApp. (ISIS has even circulated a manual recommending Signal.) But he argues that those elements have always had the incentive and ability to encrypt their communications with tougher-to-use tools like the encryption software PGP. His work, he says, is to make those protections possible for the average person without much tech savvy.

To some, Marlinspike’s logic isn’t quite as airtight as his code. Not all criminals are tech masterminds—the San Bernardino killers, for example. Former NSA attorney and Brookings Institution fellow Susan Hennessey wonders who determines which lawbreakers deserve to be wiretapped, if not a democratically elected government? Americans have long agreed, she argues, to enable a certain degree of police surveillance to prevent truly abhorrent crimes like child pornography, human trafficking, and terrorism. “We could set up our laws to reject surveillance outright, but we haven’t,” she says. “We’ve made a collective agreement that we derive value from some degree of government intru­sion.” A spokesman for the FBI, when asked to comment on Marlinspike’s law-breaking philosophy, replied, “The First Amendment protects people who hold whatever view they want. Some people are members of the KKK. I’m not going to engage in a debate with him.”

Marlinspike isn’t particularly interested in a debate, either; his mind was made up long ago, during years as an anarchist living on the fringes of society. “From very early in my life I’ve had this idea that the cops can do whatever they want, that they’re not on your team,” Marlinspike told me. “That they’re an armed, racist gang.”

Marlinspike views encryption as a preventative measure against a slide toward Orwellian fascism that makes protest and civil disobedience impossible, a threat he traces as far back as J. Edgar Hoover’s FBI wiretapping and blackmailing of Martin Luther King Jr. “Moxie is compelled by the troublemakers of history and their stories,” says Tyler Rein­hard, a designer who worked on Signal. “He sees encryption tools not as taking on the state directly but making sure that there’s still room for people to have those stories.”

ASK MARLINSPIKE TO tell his own story, and—no surprise for a privacy zealot—he’ll often answer with diversions, mono­syllables, and guarded smiles. But anyone who’s crossed paths with him seems to have an outsize anecdote: how he once biked across San Francisco carrying a 40-foot-tall sailboat mast. The time he decided to teach himself to pilot a hot-air balloon, bought a used one from Craigslist, and spent a month on crutches after crashing it in the desert. One friend swears he’s seen Marlinspike play high-stakes rock-paper-scissors dozens of times—with bets of hundreds of dollars or many hours of his time on the line—and has never seen him lose.

But before Marlinspike was a subcultural contender for “most interesting man in the world,” he was a kid growing up with a different and far less interesting name on his birth certificate, somewhere in a region of central Georgia that he describes as “one big strip mall.” His parents—who called him Moxie as a nickname—separated early on. He lived mostly with his mother, a secretary and paralegal at a string of companies. Any other family details, like his real name, are among the personal subjects he prefers not to comment on.

Marlinspike hated the curiosity-killing drudgery of school. But he had the idea to try programming videogames on an Apple II in the school library. The computer had a Basic interpreter but no hard drive or even a floppy disk to save his code. Instead, he’d retype simple programs again and again from scratch with every reboot, copying in commands from manuals to make shapes fill the screen. Browsing the computer section of a local bookstore, the preteen Marlin­spike found a copy of 2600 magazine, the catechism of the ’90s hacker scene. After his mother bought a cheap desk­top computer with a modem, he used it to trawl bulletin board services, root friends’ computers to make messages appear on their screens, and run a “war-dialer” program overnight, reaching out to distant servers at random.

“Moxie likes the idea that there is an unknown, that the world is not a com­pletely surveilled thing.”

To a bored middle schooler, it was all a revelation. “You look around and things don’t feel right, but you’ve never been anywhere else and you don’t know what you’re missing,” Marlin­spike says. “The Internet felt like a secret world hidden within this one.”

By his teens, Marlinspike was working after school for a German software company, writing developer tools. After graduating high school—barely—he headed to Silicon Valley in 1999. “I thought it would be like a William Gibson novel,” he says. “Instead it was just office parks and highways.” Jobless and homeless, he spent his first nights in San Francisco sleeping in Alamo Square Park beside his desktop computer.

Eventually, Marlinspike found a programming job at BEA-owned Web­Logic. But almost as soon as he’d broken in to the tech industry, he wanted out, bored by the routine of spending 40 hours a week in front of a keyboard. “I thought, ‘I’m supposed to do this every day for the rest of my life?’” he recalls. “I got interested in experimenting with a way to live that didn’t involve working.”

For the next few years, Marlinspike settled into a Bay Area scene that was, if not cyberpunk, at least punk. He started squatting in abandoned buildings with friends, eventually moving into an old postal service warehouse. He began bumming rides to political protests around the country and uploading free audio books to the web of himself reading anarchist theorists like Emma Goldman.

Forget Apple vs. the FBI: WhatsApp Just Switched on Encryption for a Billion People

He took up hitchhiking, then he upgraded his wanderlust to hopping freight trains. And in 2003 he spontaneously decided to learn to sail. He spent a few hundred dollars—all the money he had—on a beat-up 27-foot Catalina and rashly set out alone from San Francisco’s harbor for Mexico, teaching himself by trial and error along the way. The next year, Marlin­spike filmed his own DIY sailing documentary, called Hold Fast. It follows his journey with three friends as they navigate a rehabilitated, leaky sloop called the Pestilence from Florida to the Bahamas, finally ditching the boat in the Dominican Republic.

Even today, Marlinspike describes those reckless adven­tures in the itinerant underground as a kind of peak in his life. “Looking back, I and everyone I knew was looking for that secret world hidden in this one,” he says, repeating the same phrase he’d used to describe the early Internet. “I think we were already there.”

If anything can explain Marlinspike’s impulse for privacy, it may be that time spent off society’s grid: a set of experi­ences that have driven him to protect a less observed way of life. “I think he likes the idea that there is an unknown,” says Trevor Perrin, a security engineer who helped Marlinspike design Signal’s core protocol. “That the world is not a completely surveilled thing.”

THE KEYS TO PRIVACY

Beneath its ultrasimple interface, Moxie Marlinspike’s crypto protocol hides a Rube Goldberg machine of automated moving parts. Here’s how it works.

THROUGH THOSE YEARS, Marlinspike took for granted that authority was the enemy. He describes harbor patrols and train yard guards who harassed him and his fellow hobo voyagers. Cops evicted him from squats, hassled him in the towns he and his friends passed through, and impounded their car on what seemed to be thin pretenses. But merely going to demonstrations never felt like the right way to challenge the world’s power structures.

Instead, around 2007 he turned his political interests back to the digital world, where he’d seen a slow shift toward post–Patriot Act surveillance. “When I was young, there was something fun about the insecurity of the Internet,” he says, with its bounty of hackable flaws available to benign prank­sters. “Now Internet insecurity is used by people I don’t like against people I do: the government against the people.”

In 2008, Marlinspike settled in a decrepit brick mansion in Pittsburgh and started churning out a torrent of security software. The next year he appeared for the first time at the Black Hat security conference to demonstrate a program he called SSLstrip, which exposed a critical flaw in web encryption. In 2010 he debuted GoogleSharing, a Firefox plugin that let anyone use ­Google services anonymously.

That year, with the growth of smartphones, Marlin­spike saw his biggest opportunity yet: to secure mobile communica­tions. Helped by a friend who was getting a robotics PhD at Carnegie Mellon, he launched Whisper Systems, along with a pair of Android apps: Text­Secure, to encrypt text messages, and RedPhone, to protect voice calls. Anti-­authoritarian ideals were built in from the beginning; when the Arab Spring exploded across North Africa, Whisper Systems was ready with an Arabic version to aid protesters.

Alone in the dark, Marlin­spike clung to the hull and realized, with slow and lonely certainty, that he was very likely going to die.

Marlinspike dreamed of bringing his encryption tools to millions of people, an ambition that required some sort of business model to fund them. He moved back to San Francisco to promote Whisper Systems as a for-profit startup. The company had barely gotten off the ground when Twitter approached him with a buyout offer, hoping to use his expertise to fix the shambolic security that had led to repeated hacks of celebrity and journalist accounts. The terms of the resulting deal were never made public. Marlin­spike describes it only as “more money than I’d ever encountered before. But that’s a low bar.”

Marlinspike became the director of product security at Twitter. A coworker remembers that his expertise was “revered” within the company. But his greater goal was to alter the platform so that it didn’t keep logs of users’ IP addresses, which would make it impossible for authorities to demand someone’s identity, as they’d done with one Occupy Wall Street protester in 2012.

That project clashed with the priorities of executives, a coworker says. “Moxie couldn’t care less if Twitter made a lot of money,” the former colleague says. “He was more interested in protecting users.” Meanwhile, his contract stipulated that he’d have to work for four years before cashing out the stock he’d been paid for his startup. Marlinspike’s cypherpunk apotheosis would have to wait.

https://www.instagram.com/p/8bVAX-LOCz/embed/?v=7ONE FALL EVENING after work, Marlinspike and a friend made a simple plan to sail a 15-foot catamaran out 600 feet into the San Francisco Bay, where they’d drop anchor and row back in a smaller boat, leaving the sailboat to wait for their next adventure. (Anarchist sailors don’t like to pay dockage fees.) Marlinspike headed out into the bay on the catamaran with his friend following in a rowboat.

Only after Marlinspike had passed the pier did he realize the wind was blowing at a treacherous 30 miles an hour. He decided to turn back but discovered that he’d misrigged the craft and had to fix his mistake. As the sun sank toward the horizon, he shouted to his friend that they should give up and return to shore, and the friend rowed back to safety.

Then, without warning, the wind gusted. The catamaran flipped, throwing Marlinspike into the ice-cold water. “The suddenness of it was unbelievable, as if I was on a tiny model made of paper which someone had simply flicked with their finger,” he would later write in a blog post about the experience.

Soon the boat was fully upside down, pinned in place by the wind. Marlinspike tried to swim for shore. But the pier was too far away, the waves too strong, and he could feel his body succumbing to hypothermia, blackness creeping into the edges of his vision. He headed back to the overturned boat. Alone now in the dark, he clung to the hull, took stock of the last hour’s events, and realized, with slow and lonely certainty, that he was very likely going to die.

When a tugboat finally chanced upon his soaked and frozen form he was nearly unconscious and had to be towed up with a rope. When he arrived at the hospital, Marlinspike says, the nurses told him his temperature was so low their digital thermometers couldn’t register it. As he recovered over the next days, he had the sort of realization that sometimes results from a near-death experience. “It definitely sharpened my focus,” he says of the incident. “It made me question what I was doing with my life.”

Marlinspike’s time at Twitter had given him an ambitious sense of scale: He was determined to encrypt core chunks of the Internet.

A normal person might have quit sailing. Instead, Marlinspike quit Twitter. A year and a day after he had started, he walked away from over $1 million in company stock.

Marlinspike quickly picked up where he’d left off. In early 2013 he relaunched his startup as an open source project called Open Whisper Systems. To fund it, he turned to Dan Meredith, director of the Open Technology Fund, a group supported by the Broad­casting Board of Governors, best known for running Radio Free Europe. Meredith had long admired Marlinspike’s encryption apps. As a former security tech at Al Jazeera, he had relied on them to protect reporters and sources during the Arab Spring. “They were what our most sensitive sources used,” Meredith says. “I knew Moxie could do this, and we had the money to make it possible.” The OTF gave Open Whisper Systems around $500,000 in its first year and in total has funneled close to $2.3 million to the group.

With that funding and more from wealthy donors that Marlinspike declines to name, he began recruiting devel­opers and hosting them at periodic retreats in Hawaii, where they’d alternate surfing and coding. In quick succession, Open Whisper Systems released Signal and then versions for Android and the Chrome browser. (Open Whisper Systems has since integrated changes from dozens of open source contributors but still uses the same cryptographic skeleton laid out by Marlinspike and Trevor Perrin in 2013.)

Marlinspike’s time at Twitter had given him an ambitious sense of scale: He was determined to encrypt core chunks of the Internet, not just its fringes. By chance, he met a Whats­App engineer at a family reunion his girlfriend at the time threw at his house. Through that connection, Marlinspike wangled a meeting with WhatsApp’s cofounder Brian Acton. Later, Marlinspike met with the company’s other cofounder, Jan Koum, who had grown up in Soviet Ukraine under the constant threat of KGB eavesdropping.

Both men were almost immediately interested in using Marlinspike’s protocols to protect WhatsApp’s international users, particularly its massive user bases in privacy-loving Germany and surveillance regimes in the Middle East and South America. “We were aligned pretty early,” Acton says. “When we got past the hairstyle, we were like, ‘Let’s get down to business.’”

IN A HOTEL ROOM above San Francisco’s Soma district a few hours after his RSA panel, Marlinspike pulls out a slim laptop and enters his password to decrypt its hard drive. Or rather, attempts to; the string of characters is so long and complex that he mistypes it three times and, with a slightly embarrassed grin, has to reboot the computer. Finally he succeeds and opens a video file. It’s a rough cut of an ad for Signal he’s hoping to spread online, a montage of footage of the Russian punk protest band Pussy Riot, Daniel Ellsberg, Jesse Owens, Hong Kong’s pro-­democracy Umbrella protesters, and Martin Luther King Jr. “They tell us to stay quiet and follow the rules,” a rough voice intones over the images. “We believe in the power of your words … Speak up, send a message.”

Marlinspike’s intention with the spot, whose script he wrote, was to create a “Nike ad for privacy,” he says. “Nike has a boring product. They don’t talk about the shoes. They celebrate great athletes. We’re trying to do the same thing, celebrating people with a contestational relationship to power. Activists, whistle-blowers, journalists, artists.”

“The big win is when a billion people are using WhatsApp and don’t even know it’s encrypted. I think we’ve already won the future.”

Today, those people include Edward Snowden, who has written that he uses Signal “every day.” (Marlinspike recently visited the exiled whistle-blower in Moscow.) Laura Poitras, the Pulitzer- and Oscar-­winning recipient of Snowden’s NSA leaks, recommends it to docu­mentary filmmakers and journalists. Women’s rights activists in Latin America who help women find abortions use Signal. So do North Korean defectors evading Kim Jong-un’s spies. Attorneys at the National Lawyers Guild use it to speak about clients. Members of Hands Up United, one of the groups leading the Black Lives Matter movement in Ferguson, Missouri, two years ago, started using Signal after noticing police cars following them home or parked outside of their meetings and strange tones and dropped calls on their cell phones. (The Intercept revealed last summer that the Department of Homeland Security monitored the protesters.) “Signal gave us so much confidence to continue our work,” says Hands Up United organizer Idalin Bobé.

But these are only the early adopters in Marlinspike’s master plan. He outlines his endgame: In the past, government-friendly phone companies have practically partnered with law enforcement to make wiretaps easy. Now people are increasingly shifting to what he calls overlay services—apps like WhatsApp and Facebook Messenger—to communicate. And that switch offers a chance to start fresh, with a communications infrastructure that can be built to resist surveillance. “The big win for us is when a billion people are using WhatsApp and they don’t even know it’s encrypted,” Marlinspike says. “At this point, I think we’ve already won the future.”

https://www.instagram.com/p/_KvwFCrOOu/embed/captioned/?v=7THE NEXT DAY, Marlinspike is rushing over to Open Whisper Systems headquarters, where he’s late for a meeting. As I speed-walk to keep up with his long legs, he grouses about the day-to-day of running a software project: the bug reports and constant tweaks to keep up with operating systems’ improvements, the deadening hours of sitting in front of a computer.

Marlinspike surprises me by admitting that he looks forward to the moment when he can quit. “Someday Signal will fade away,” he states unsentimentally. Instead, he says, Open Whisper System’s legacy will be the changes Signal will have inspired in better-funded, for-profit communi­cation apps.

That time may not be so far off. “I don’t really want to do this with the rest of my life,” Marlin­spike says. “Eventually, you have to declare victory.”

But cypherpunks like Marlinspike—let’s be honest—haven’t yet won the crypto war. In fact, the war may be unwinnable by either side. If the rise of end-to-end encrypted messaging enables the sort of benign law breaking Marlinspike has preached, sooner or later it will also shield some indefen­sible crimes. And that means every technological move toward privacy will be answered with a legal one aimed at shifting the equilibrium back toward surveillance: If law enforcement continues to be foiled by uncrackable encryption, it will come back with an order for “technical assistance,” demanding companies weaken their security measures and rewrite their code to help the cops, as the FBI demanded of Apple. Some form of crypto backdoor might even be built in secret. And Congress still threatens to advance legislation that could ban user-­controlled encryption outright.

But these legal and political battles may not be Marlin­spike’s to fight. “He definitely romanticizes being an amateur,” says one particularly frank friend. “He likes to give up once he’s an expert.” Marlinspike, she says, seeks the “zero point, when you have nothing to lose, when you have no property, no lover, nothing to hold you back.”

Cypherpunks like Marlin­spike haven’t yet won the crypto war. In fact, the war may be unwinnable by either side.

I’m reminded of that underlying restlessness on the last evening I spend with Marlinspike, at a Sunday night screening of Hold Fast, hosted by a sailing club at the Berkeley Marina. As his doc plays to a crowd of a few dozen people, we sit in the back next to a wood-burning stove, with a spring storm churning the bay outside the window behind us.

Early in the film, the narration goes off on a tangent, telling the story of Bernard Moitessier, whom Marlinspike describes reverentially as a sailing mystic. In 1969, Moites­sier was winning the Golden Globe, a solo, globe-circling yacht race. Moitessier, a monklike eccentric, didn’t even carry a radio, instead using a slingshot to hurl film canisters containing messages to nearby ships. Just as Moitessier was set to finish ahead of his competitors in Plymouth, England, he shot off a message rejecting the competition and explaining that he would rather simply keep sailing for the Pacific Islands. “I am continuing nonstop because I am happy at sea,” the note read, “and perhaps because I want to save my soul.”

When the screening ends, the lights come up and Marlin­spike takes questions. A middle-aged woman asks him what he’s doing now, nine years after the film’s release. Along with plenty of other people in this audience, she knows him only as Moxie Marlinspike the rogue sailor, not as a cryptographer.

Marlinspike takes a second to think, as if he’s never actually considered the question before. “I don’t know,” he says finally, sighing with what sounds like sincere uncertainty. “Maybe I should go back to sailing cheap.”

The crowd laughs at Marlinspike’s show of self-effacing confusion. But he seems to mean what he says. And over their heads, out the window, past the bay, lies the Pacific Ocean: dark, unknown, and inviting.