Article by Peter Maass

The Philosopher of Surveillance

The Intercept  |  August 11, 2015
What Happens When a Failed Writer Becomes a Loyal Spy?

ARE YOU THE SOCRATES of the National Security Agency?

That was the question the NSA asked its workforce in a memo soliciting applications for an in-house ethicist who would write a philosophically minded column about signals intelligence. The column, which would be posted on a classified network at the NSA, should be absorbing and original, the memo said, asking applicants to submit a sample to show they had what it takes to be the “Socrates of SIGINT.”

In 2012, the column was given to an analyst in the Signals Intelligence Directorate who wrote that initially he opposed the government watching everyone but came around to total surveillance after a polygraph exam did not go well. In a turn of events that was half-Sartre and half-Blade Runner, he explained that he was sure he failed the polygraph because the examiner did not know enough about his life to understand why at times the needle jumped.

“One of the many thoughts that continually went through my mind was that if I had to reveal part of my personal life to my employer, I’d really rather reveal all of it,” he wrote. “Partial revelation, such as the fact that answering question X made my pulse quicken, led to misunderstandings.”

He was fully aware of his statement’s implications.

“I found myself wishing that my life would be constantly and completely monitored,” he continued. “It might seem odd that a self-professed libertarian would wish an Orwellian dystopia on himself, but here was my rationale: If people knew a few things about me, I might seem suspicious. But if people knew everything about me, they’d see they had nothing to fear. This is the attitude I have brought to SIGINT work since then.”

When intelligence officials justify surveillance, they tend to use the stilted language of national security, and we typically hear only from senior officials who stick to their platitudes. It is rare for mid-level experts — the ones conducting the actual surveillance — to frankly explain what they do and why. And in this case, the candid confessions come from the NSA’s own surveillance philosopher. The columns answer a sociological curiosity: How does working at an intelligence agency turn a privacy hawk into a prophet of eavesdropping?

Not long after joining the NSA, Socrates was assigned a diplomatic target. He knew the saying by Henry Stimson that “gentlemen do not read each other’s mail,” and he felt uncomfortable doing the digital equivalent of it. As he wrote, “If there were any place in the world that idealism should rule and we should show voluntary restraint in our intelligence work, diplomacy was that place. Terrorists who meant harm to children and puppies were one thing, but civil servants talking about work while schlepping their kids to soccer practice seemed a little too close to home.”

His polygraph was an epiphany, however.

“We tend to mistrust what we do not understand well,” he noted. “A target that has no ill will to the U.S., but which is being monitored, needs better and more monitoring, not less. So if we’re in for a penny, we need to be in for a pound.”

I wanted to know more about Socrates, but one of the asymmetric oddities of the NSA is that the agency permits itself to know whatever it wants to know about any of us, yet does everything it can to prevent us from knowing anything about the men and women who surveil us, aside from a handful of senior officials who function as the agency’s public face. An NSA spokesperson refused to confirm that Socrates even worked there. “I don’t have anything to provide for your research,” the spokesperson wrote in an email.

The “SIGINT Philosopher” columns, provided to The Intercept by NSA whistleblower Edward Snowden, gave me the opportunity to learn more without the agency’s assistance, because they included his name. Heading down the path of collecting information about Socrates (whose name we are not publishing — more on that later), I was in the odd position of conducting surveillance on a proponent of surveillance, so I had a get-out-of-guilt-free card.

Unlike the paranoid eavesdropper played by Gene Hackman in The Conversation, or the quiet Stasi agent at the center of The Lives of Others, Socrates lives in the age of Google and data-mining. Like the rest of us, he cannot remain invisible. Socrates was an evangelical Christian for seven years, got married at 19, divorced at 27 and remarried not long after. He is now a registered Democrat and lives in a Maryland suburb with his son and wife, a public school teacher. I’ve seen the inside of their house, thanks to a real estate listing; the home, on a cul de sac, has four bedrooms, is more than 2,000 square feet, and has a nice wooden deck. I’ve also seen pictures of their son, because Socrates and his wife posted family snapshots on their Facebook accounts. His wife was on Twitter.

Conducting surveillance can be a creepily invasive procedure, as Socrates discovered while peering into the digital life of his first diplomatic target, and as I discovered while collecting information about him. In the abstract, surveillance might seem an antiseptic activity — just a matter of figuring out whether a valid security reason exists to surveil a target and then executing a computer command and letting the algorithms do the rest. But it’s not always that clinical. Sheelagh McNeill, the research editor with whom I worked on this story, was able to find Socrates’ phone number, and although he did not respond to voicemails, he eventually got on the line when I called at night.

His young son answered and fetched his father. Socrates was not pleased. He asked that I not disclose his identity, which was ironic because his columns praised the virtues of total transparency as a way to build trust. Why shouldn’t the public know about him? What’s wrong with a bit of well-intentioned surveillance among fellow Americans? I was not able to ask these questions, however.

“I can’t say anything,” he said, not long before he hung up. “You can’t use my name.”

He didn’t need to say anything, because his NSA columns explained a lot, as did the online databases McNeill and I consulted, though all of it paled in comparison to the motherlode of his blog.


The name on Socrates’ columns was not, it turned out, his full legal name; he used an abbreviated form of his first name. His last name is an ordinary one that yields a large number of search results. McNeill and I had a bit of luck, though — his columns included a user ID with his middle initial. McNeill needed a day to comb the web and examine public as well as proprietary databases before finding a person she believed was Socrates. He resided in the Washington area, was married to a woman who had worked in Korea (Socrates is a Korean language analyst), and he had lived in a variety of places that correlated with biographical hints in the columns.

But there wasn’t a lot of flesh on the digital bones we had found; Socrates was correct when he said it’s easy to misunderstand someone if you know only a bit. McNeill and I, though fairly certain that we had located the right person, still didn’t know much about his life or who, in an existential sense, he was. That changed when McNeill typed his name into Google and the name of a world event that one of his columns had mentioned.

She walked to my desk with her laptop open and pointed to a blog on her screen.

“This is him,” she said.

The blog consists of more than 20,000 words Socrates wrote about his failed effort, before joining the NSA, to earn a living as a writer. As he explained in often bitter and personal detail, he reluctantly went from starving writer to salaried spy. Instead of creating fictional characters, he spied on real ones. It dawned on me: coming from the world of books and words rather than technology and code, Socrates represented a post-modern version of the literary eavesdropper.

In his twenties, according to his blog, he wrote a personal mission statement, in the style of Jerry Maguire, in which he described the creation of literature as a higher calling than raising a child, proclaiming it nobler to live as a penniless writer than a parent. He took subsistence jobs to pay the bills and relied on financial support from family members as he tried to become the next Jonathan Franzen. He loved the great authors he read and studied — Melville, Cervantes, Borges, Vonnegut, and others. He wanted to produce great works that would persuade people to love and care about the world as much as he did.

It didn’t work out, and ironically the turning point was a graduate writing program he enrolled in at a Midwestern university in 2002. The program used the workshop method of putting students into a group and having them read and critique one another’s work. His experience amounted to a year and a half of getting bad advice from bad writers working part-time jobs to put themselves through a middling school. Nearly every professor was a dick, he wrote, and he mused that writing had turned them into dicks.

The worst part of the experience was the financial side, because he went into debt (annual tuition and living costs at his university can exceed $25,000). Tired of asking for handouts and getting rejection letters, he wrote in his blog that the nobility of writing was a lie. He was so angry with himself and his writing that he deleted everything he had written, even throwing away hard copies of his stories, and stopped reading literature altogether. He decided to look for real work.

Socrates was able to land a job at the NSA. He had a background in Korean, which is of great interest in the intelligence world. He worked hard, had a son, owned a house, did volunteer work with refugees. He was living the American dream. In 2012, he began the “SIGINT Philosopher” columns, and this seems to have reminded him of the joys and rewards of writing for an audience. The next year, according to his blog, he thought he might lose his day job and this crisis made him ask what he most wanted to do in life. The answer surprised him: He wanted to write.

He was having, as he frankly admitted, a mid-life crisis that turned into a writing experiment. After 10 years of ignoring literature, he set a goal — he would write a collection of stories for an annual competition organized by the University of Iowa Press. He had a bit less than a year to write the stories, while keeping his position at the NSA. In the summer of 2014, a month before the Iowa deadline and just before one of his stories was published in a small literary review, he started blogging, without mentioning that he was a spy.

The surveillance archetypes that dominate popular culture are different from Socrates because they eventually see evil in the systems of surveillance that employ them. There is Winston Smith in 1984, who works at the Ministry of Truth and despises everything it does. Gerd Wiesler in The Lives of Others turns insubordinate after he receives an assignment to surveil a well-known writer and his girlfriend. And Harry Caul in The Conversation comes to fear that he is being played by the business executive who hired him.

Socrates, on the other hand, is loyal to a fault. One of his columns made a point of saying that even if an NSA employee disagrees with a policy, and even if the policy is wrong, she should stay the course. “We probably all have something we know a lot about that is being handled at a higher level in a manner we’re not entirely happy about,” he wrote. “This can cause great cognitive dissonance for us, because we may feel our work is being used to help the government follow a policy we feel is bad.” Socrates advised modesty. Maybe the policy is actually correct — or perhaps it is wrong but will work out in the end. “I try,” he explained, “to be a good lieutenant and good civil servant of even the policies I think are misguided.”

Socrates does not have a quiet psyche, however. While his blog and columns do not question the NSA, he struggled to live meaningfully. He returned to creative writing to make a lasting and worthwhile mark, so that his time on earth would not be wasted. Unfortunately, his second effort to become a successful writer did not turn out any better than the first. He reached out to two writing groups but never heard back. He paid for an editor to review one of his stories, disagreed with the editor’s comments, and accused the editor of trying to drum up additional fees for more work — and blogged about all of this in excruciating detail. The story, about a man whose ex-girlfriend gives him herpes, was called “Infection.”

Socrates sent his stories to literary reviews and got rejection after rejection. Late last year, he wrote that he felt empty and low. His blogging platform allows for tags for each post, and the tags he used included “rejection,” “rejection notes,” “giving up” and “why write?” Even worse was the silence that greeted the one story he had gotten published after he started blogging. He heard nothing from readers, and he wondered whether anyone other than family members and friends were aware of it.

THE INTERCEPT HAS A POLICY of not publishing the names of non-public intelligence officials unless there is a compelling reason, as with our naming of Alfreda Bikowsky, who oversaw key aspects of the CIA’s torture program. Withholding Socrates’ identity presents certain problems in the age of Google, however. If I quote from his blog, or give its name, or provide other search-enhancing morsels, like the name or location of his graduate writing program or where he was born, I might provide the sort of data that could instantly reveal his name with a few keystrokes.

So I am more or less trying to do what the NSA and a large number of agencies and corporations do with the personal data they possess — stripping away names and other identifying information to “anonymize” the data before sharing it. The beauty of anonymizing data, according to the (very many) entities that do it, is that nobody can be identified — citizens and consumers do not have to worry that their privacy is violated when petabytes of data are collected about what they do, where they go, what they read, where they eat and what they buy, because their names are not attached to it. The conceit is that our data does not betray us.

Anonymization is problematic, however, because it doesn’t always work. It is entirely possible that a reader of this story could make a few lucky or smart guesses and data-mine their way to Socrates’ name. There is a whole area of data research that’s known as re-identification, which consists of matching anonymized data with actual names. Even if anonymization did work, there’s a creepiness to knowing everything about a person even if you don’t know their name. Look at this story — it’s invasive without disclosing Socrates’ name, isn’t it? I could dial up the invasiveness, too. Would you like to know the asking price of the house he lives in? Would you like to know the names of the schools where his wife has worked? Would you like to see the pictures of their son or their house? Know the name of their dog? Their dates of birth? The branch of the military Socrates served in and his dates of service? There is so much I can tell you about Socrates without telling you his name. You don’t need to code if you want to hack into someone’s life. We are all hackers now.

If the original Socrates of ancient Greece were still around, he would probably suggest that it is morally compromising to conduct surveillance on people who have done no harm — no matter whether the surveillance is carried out by a philosopher in a robe, a journalist with a laptop, or an intelligence agency with a $10 billion budget. Surveillance, as a word, is a cleaned-up version of voyeurism, and whether state-sponsored or editor-approved, it’s creepy to carry out, and probably futile in most cases. Socrates (the columnist) insisted that total surveillance would allow the NSA to understand us and not mistake our intentions. His inaugural column even suggested that the NSA’s slogan could be “building informed decision makers — so that targets do not suffer our nation’s wrath unless they really deserve it — by exercising deity-like monitoring of the target.” Yet Socrates probably knows, as most writers do, that what we say does not necessarily reflect what is in our minds.

Here’s an example. I told Socrates, in our phone call, that I had read his blog. I assumed that once our conversation was finished he would go online and take down the blog, scrupulously doing what a smart surveiller would do once he realized he was the target rather than targeter — try to scrub the public domain of his existence to inhibit surveillance of him.

Yet the blog stayed up. In fact, he continued posting — once about a blockbuster movie series he disliked, another time about a short story he generally liked. I asked McNeill, the research editor, what she made of this, and she was surprised, too. Although I could not spy on Socrates in the way the NSA spies on its targets, I had done a lot and thought I understood him. In addition to the biographical and financial data I had mined, Socrates and I have an intellectual kinship as writers. After all, editors have killed stories I have written. I have friends who have gone through graduate writing programs. I have taught in one. I have the same hope (probably futile) that my writing will do some good in this world and somebody in Hollywood will make a movie.

Yet I had misunderstood him. I’m not sure I can ever understand him, even if he were strapped into a polygraph and had all the time in the world to answer my questions. If it is true that we are mysteries even to ourselves — as the original Socrates suggested — the eavesdroppers at the NSA invade our privacy without learning who we really are.