This Machine Kills Secrets covers a half-century of leaking, from the Pentagon Papers to new projects such as OpenWatch and Cop Recorder. You interviewed many of the key participants, spending a lot of time among crypto-libertarians, hackers, and information activists. What was the most surprising thing you discovered within that milieu?

Maybe the thing that surprised me the most, as I dug into the history of the cypherpunks that leads up to WikiLeaks, was just how far back this dream of using anonymity and untraceable information as a weapon against authority originates. Tim May’s “Crypto-Anarchist Manifesto” and his BlackNet experiment wrapped in most of the key ideas that WikiLeaks would use literally 20 years later to obtain and publish its megaleaks of classified info, despite the fact that most of the necessary technologies didn’t even exist back in the early 90s when May was writing.

I was surprised to find again and again that the Cypherpunk Mail List that Tim May co-founded was cited as an influence by so many characters in this story of the history of anonymity and anonymous data leaks, including John Young (the co-founder of Cryptome), the creators of the anonymity software Tor, to Jacob Appelbaum and of course Julian Assange. It all fit together much more neatly than I expected, and it made it clear that WikiLeaks really isn’t the story, so much as an episode in a movement that existed before WikiLeaks and will persist after WikiLeaks is gone.

Wikileaks seems like a germ of an idea always on the verge of becoming reality: from Tim May’s BlackNet proposal on the cypherpunk mailing list to Roger Dingledine’s idea of a distributed, anonymous publishing system (which would later become the Tor project). And of course there’s John Young’s long-running Cryptome, a Wikileaks without the pretense of secure leaking. But what had to come together for Wikileaks to actually happen?

I think a couple of things came together in WikiLeaks: Tor became a powerful and relatively secure anonymity tool, and Assange was more willing than John Young to rely on its security. And just as importantly, Assange turned out to be the perfect character necessary to inspire leakers. Not only did he have the technical skills to build WikiLeaks, but he was also eloquent, ultra-confident, and had a hacker convict past that gave him this unimpeachable anti-authoritarian credibility. Those personal qualities were a kind of catalyst for the ingredients that had been percolating since the early days of the cypherpunks — the “kitchen-sink nitroglycerin” in the cypherpunk “blast-shack” that Bruce Sterling wrote about in his awesome essay of that name.

Andy Greenberg holding one of the Wikileaks servers

You’re the only journalist to knowingly interview The Architect, the engineer behind the original Wikileaks technology. He and another co-founder left the organization with a lot of hostility, vowing to create their own, competitive site, OpenLeaks. But nothing seems to have happened. Do you have any insight on that?

I haven’t actually spoken with Daniel Domscheit-Berg since the book published, and the Architect declined to speak with me again after our first and only interview. (I was lucky to get him once.) It may be that OpenLeaks is still waiting for the right moment to launch. Both the Architect and DDB are perfectionists, and won’t launch until they’re ready. But I imagine they also face enormous hurdles due to their reputation as turncoats among so much of the hacker community.

As I detail in the last chapter of the book, WikiLeaks and OpenLeaks sabotaged each other very effectively.

You take a historically minded approach in the book, establishing a lineage of leaking that, for example, connects accused Wikileaks source Bradley Manning to Pentagon Papers leaker Daniel Ellsberg. It took Ellsberg nearly a year of photocopying, cutting, and printing; Manning exfiltrated an exponentially larger cache of documents using a rewritable CD masquerading as a Lady Gaga disc. So advances in information technology have enabled both secret-keepers and secret-sharers. But you also point out that in 1969 Daniel Ellsberg occupied a rarefied position within the RAND Corporation, and his leak involved documents with a higher top-secret classification than the Wikileaks material. Manning, meanwhile, was a lowly private, yet one among 1.2 million Americans with a top-secret security clearance. Is there a near-paradox here — more secrets, with more people having access to them?

The lesson of WikiLeaks is that shared secrets leak. Eventually even WikiLeaks became enough of an institution itself that it had shared secrets that leaked, including the disastrous leak of the unredacted Cablegate database in the summer of 2011. In the case of the U.S. Government, which has granted millions of people classified access to so-called “secret” and “top-secret” information, it does seem inevitable that one of them leaked a large collection of that data.

It won’t be surprising when it happens again. In fact, it may have happened again to some degree with this Swiss intelligence agency technician who apparently walked out with terabytes of secret data.

The early cypherpunks you interviewed, people like Tim May and David Chaum, hold very optimistic beliefs about the power of cryptography to protect individual liberty. And as you point out, Bradley Manning wasn’t tracked down by technology, but by an informant. But he’s still imprisoned, and other whistleblowers such as former NSA analyst Thomas Drake have been prosecuted to an unprecedented degree: the Obama administration has pursued twice as many Espionage Act charges as all previous administration. Technologically this might be a golden age of leaking, but the legal arena seems a different matter.

The Obama administration has been amazingly unfriendly to whistleblowers who leak classified information. But it seems to me that those efforts only push leakers of sensitive data away from traditional, vulnerable mainstream media outlets, towards platforms WikiLeaks that (at least at one time) could be trusted to protect their anonymity. Unfortunately for leakers, WikiLeaks no longer operates a submissions system, and it doesn’t seem like any other trusted leaking platform exists right now, either.