Gray Day: My Undercover Mission to Expose America's First Cyber Spy

Gray Day: My Undercover Mission to Expose America's First Cyber Spy

by Eric O'Neill
Gray Day: My Undercover Mission to Expose America's First Cyber Spy

Gray Day: My Undercover Mission to Expose America's First Cyber Spy

by Eric O'Neill


    Qualifies for Free Shipping
    Check Availability at Nearby Stores

Related collections and offers


A cybersecurity expert and former FBI “ghost” tells the thrilling story of how he helped take down notorious FBI mole Robert Hanssen, the first Russian cyber spy.

“Both a real-life, tension-packed thriller and a persuasive argument for traditional intelligence work in the information age.”—Bruce Schneier, New York Times bestselling author of Data and Goliath and Click Here to Kill Everybody

Eric O’Neill was only twenty-six when he was tapped for the case of a lifetime: a one-on-one undercover investigation of the FBI’s top target, a man suspected of spying for the Russians for nearly two decades, giving up nuclear secrets, compromising intelligence, and betraying US assets. With zero training in face-to-face investigation, O’Neill found himself in a windowless, high-security office in the newly formed Information Assurance Section, tasked officially with helping the FBI secure its outdated computer system against hackers and spies—and unofficially with collecting evidence against his new boss, Robert Hanssen, an exacting and rage-prone veteran agent with a fondness for handguns. In the months that follow, O’Neill’s self-esteem and young marriage unravel under the pressure of life in Room 9930, and he questions the very purpose of his mission. But as Hanssen outmaneuvers an intelligence community struggling to keep up with the new reality of cybersecurity, he also teaches O’Neill the game of spycraft. The student will just have to learn to outplay his teacher if he wants to win.
A tension-packed stew of power, paranoia, and psychological manipulation, Gray Day is also a cautionary tale of how the United States allowed Russia to become dominant in cyberespionage—and how we might begin to catch up.

Product Details

ISBN-13: 9780525573524
Publisher: Crown Publishing Group
Publication date: 03/26/2019
Pages: 304
Product dimensions: 6.30(w) x 9.20(h) x 1.10(d)

About the Author

Eric O'Neill is a cybersecurity expert and former FBI counterterrorism and counterintelligence operative. He is the founder of the Georgetown Group, serves as national security strategist for Carbon Black, and is the General Counsel for Global Communities. He lectures internationally about espionage and national security, cybersecurity, hacking and fraud, and corporate diligence and defense, and has appeared as a national security expert on CNN and Fox. O'Neill is a graduate of Auburn University and the George Washington University School of Law.

Read an Excerpt

Chapter 1

Tipping Points

December 10, 2000—Sunday

Phones should not ring on Sunday mornings. I rolled across the bed, scooped my battered Nokia from the nightstand, and burrowed back under the covers. Our English basement apartment reminded me of winter camping trips I’d gone on as a Boy Scout. The single-pane windows trapped about as much heat as a canvas tent.

Juliana peered at me over the thick comforter. Her eyes were glazed with sleep, and her blond hair was piled around her head like windblown thistle. We’d been married four months, and each morning I woke beside her was a revelation. I checked the time—8:00 a.m. I was about to slap the phone down on the receiver when the voice on the other end made me freeze. All thoughts of a lazy morning flushed out of my mind. It was Supervisory Special Agent Gene McClelland.

“Don’t bother getting dressed up,” he said. “Just lace up your shoes. I’m parked out front.”

As I fumbled for my pants, my mind raced through possible scenarios, all of them grim. It was unheard-of for an FBI supervisor, the man in charge of my entire squad, to show up at a private residence on a Sunday morning. To put this into perspective, imagine your boss—the president or manager of your company—arriving at your house early one weekend morning. If you are the boss, imagine the chairman of your board parked in your driveway. If you are the chairman, imagine POTUS himself dropping by, waiting for you to appear. This was worse than any of that.

FBI supervisors never come to you. They summon. Gene showing up at my apartment could only mean something was wrong. I pulled a George Washington University Law sweatshirt over my head and took a deep breath. “No idea what’s going on, but Gene is parked outside.” The concern on Juliana’s face made me pause. “I’ll be right back.” Then I swallowed my hollow words and turned to leave.

I eased through the front door out onto the sparse lawn. Number 626 was only a few steps away from E Street, and a quick jog away from the US Capitol Building. Our building squatted between expensive town houses like an ugly sibling in a family portrait. The crammed one-bedroom sometimes felt like a closet, and we’d found mold behind the walls and in the lone heater, but it was all we could afford.

As the wind hit my face, I looked up. No one on the surrounding rooftops or balconies. I did a quick lateral scan and saw the red splash of a cardinal light upon a telephone wire. A runner huffed his Spandexed way down E Street, and the distant noise of traffic droned from nearby Pennsylvania Avenue like waves on a beach. Only one car I didn’t recognize was parked on the street. Gene.

Each step away from the building made me wince, but no SWAT vans came crashing around the corner, sirens blazing. Instead, the window of the idling sedan rolled down. “Get in,” Gene said.

I slid into the passenger seat and closed the door against the December chill.

Gene didn’t bother with niceties. “Have you ever heard of Robert Hanssen?”

I hadn’t. “Should I have?” I asked.

“No,” Gene smiled. “That’s good.”

I nodded.

“That’s why we chose you.”

I stayed silent, trying to parse the insult from the compliment. The only certainty was that I’d been left in the dark—again. For months now, I hadn’t been able to pursue any of my normal, high-priority targets for the FBI. I’d been slapped on the wrist, shuffled into the minor league. Not because I’d messed up a lead or bungled a case, but because I’d married Juliana—a German national.

No one had told me that FBI operatives with high security clearance are required to fill out a permission form before proposing to the love of their life. The FBI had instituted the policy after a few agents married into the mob. Meet the perfect girl, marry her, and then learn that her father is an FBI organized-crime target. Not the brightest moments for the universe’s premier investigative agency.

Still, imagine my shock when I bounced into the office to let my team know that I’d proposed marriage to the most wonderful girl, and my supervisor asked after my engagement form.

Then imagine me telling the FBI brass that my new bride hailed from Brandenburg, Germany. Faces that were rarely cheerful turned to stone. “You should have reported contact with an East German national,” they said.

“Don’t you mean German national?” I asked. “Haven’t you heard of reunification? There is no more East Germany.”

“Not to us.”

The FBI benched me while the FBI legat, or legal attaché office, in Germany investigated my in-laws. Think of a whale trapped on a sandy beach desperate to get back into the water. That was me. I sat in the office day after day with a suspended security clearance, working on a target-acquisition database I’d developed, until the FBI convinced itself that Juliana was not a spy. The investigation into Juliana’s family occurred before I had a chance to meet them, and I’m still pretty convinced my in-laws think I’m Stasi. They aren’t far off.

By this point I’d been in the FBI nearly five years working as an investigative specialist, otherwise known as an “investigator,” but better known as a ghost. Not too many years before I typed up my FBI application, the agency realized that Russian targets could run circles around special agents, who focused on criminal investigations and technological and research-based counter­intelligence. This was especially the case just after World War II, when a target could look over his shoulder and see a legion of buzz-cut, well-suited white males swarming him. Not exactly subtle. Without specialized surveillance and undercover investigative training, the agents were at a constant disadvantage: the Russians had more operatives and better tradecraft. The FBI was stuck solving crimes after the fact, when what it needed to do was stop the spies before they committed those crimes.

The special agents were already overburdened. So the agency decided to try something new. In the age-old tradition of American innovation, we traveled back across the pond to learn how MI5 handles surveillance in the United Kingdom through a specialized group called the Watchers. MI5’s secretive group had elevated surveillance to an art form. Nothing would stand between a Watcher and his target. A story I once heard placed two Watchers in a canoe floating within a murky water tower, watching their target through a hole drilled in the tower’s metal shell. There were a lot of stories like that. The FBI took everything the Watchers could do and made it better. The ghosts were born.

My training allowed me to follow a person from sunup to sundown, know what he ate for breakfast, and count how many times he tied his shoes or checked his watch. I could track each smile, know whom he met or whom he tried to avoid, log where he went and how he got there and everything in between. I’d learn his tradecraft and look like I’d practiced it longer than he had. I was a professional driver and photographer, didn’t need to sleep, and could stare at a single door for hours, just waiting for him to walk through.

My dark brown hair, hazel eyes, and slightly olive complexion—a gift from my Italian mother—meant that I could easily pass for a number of ethnicities, and thanks to my father’s burly genes, I could grow a beard in a matter of days. I was a master of disguise, of social engineering, of sweet-talking my way past situations. I had a badge but never used it. A target might see me a dozen times across a day’s work, but he wouldn’t notice me. I was trained to blend into situations, to find cover in plain sight, to look unobtrusive, uninteresting, and unremarkable. I’d call in a spy before he spied or committed an act of terrorism, then melt into the shadows while he was still wondering where all the FBI agents had suddenly come from. I knew how to be gray.

“Who’s Hanssen?” I asked.

Gene shrugged. “We think he’s a spy. We want you to investigate him.”

It took me a moment to get the words past my teeth. “Gene. You woke me up on a Sunday morning, dragged me out of bed, scared the hell out of me by coming here, all to ask me to do my job? Couldn’t this have waited until Monday?”

Gene shook his head. “We don’t want you to ghost him, Eric. We want you to investigate him. Face-to-face.”

I sat there, frozen.

“We need someone on the ground with him,” Gene explained. “To develop a relationship, try to get some dirt. I’ve recommended you.”

I opened and closed my mouth like a guppy gasping for oxygen. Gene had asked me to participate in what amounted to an elicitation operation—one where the undercover asset engages in conversation, memorizes details, learns facts, and draws out information. I’d been involved in high-risk cases, but I’d never been instructed to interact with a target face-to-face; my job was to play a backstage part out of sightlines. For the first time, Gene was asking me to play myself. I probably did look like a fish—one miles away from water.

“I need your answer. In or out.”

There are tipping points in every life. Tiny moments in time when we’re forced to make a choice: take the leap or stand by and let the opportunity pass. These are the moments that shape a future.

This was one of mine.

“What do I tell Juliana?”

Gene scratched his head. “I dunno. Tell her you got promoted. You’ll be assigned to a computer job at headquarters.” His eyes hardened. “I don’t have to tell you to keep the rest quiet. As far as you are concerned, the only people that know about this are you and me. Juliana can’t know anything.”

I got it. Although Juliana knew I worked for the FBI, we had a deal never to discuss it. She once told me that she enjoyed having a husband who never spoke about work. We’d talk about other things—hopes and dreams, the drama her fellow business students got up to, our long-running debate about whether American football was better than European soccer—but never about what I did all day.

“Gene,” I said. “I’m keying in on the word ‘promotion.’ If I really need to sell this . . .” Now I was the one smiling.

“Okay, okay, Eric.” Gene’s short chuckle faded into a cough. “I’ll get you some extra overtime. You’ll more than earn it.” He put the car into drive. “In or out.”

I leapt.

Target: Robert Hanssen

Suspected spy


The Tyranny of Secrets

There is no such thing as a lie detector. Despite numerous advances in behavioral science and technology, a person cannot use facial expressions or verbal “tells” to sniff out a lie with a great deal of certainty. Nor can a machine measure the thoughts that speed through a person’s mind.

How do crack investigators sort lies from truth when they have a suspect in the interview chair? They combine a little psychology, a little technology, and a dash of Hollywood stagecraft. The standard polygraph machine measures pulse, blood pressure, respiration, and skin conductivity while a person is asked specific questions. Today these metrics are graphed on a computer screen, but in the past the machine scratched ink across an ever-expanding roll of graph paper. In theory, a deceptive response to a particular question will spike some or all of the physiological indicators—a quickened pulse, a sweaty palm.

But the machine is not infallible, and accurate results require an expert examiner. Spies have developed many ploys and countermeasures to defeat the machine. An old story about Russian spymasters stands out: When American moles were being trained by their Russian handlers to make dead drops and other clandestine exchanges, the Russian intelligence officer in charge provided advice on how to defeat a US intelligence agency’s standard polygraph. One such countermeasure, typical of Russia’s often brutal espionage tactics, was to step on a tack that the spy had hidden in the toe of his shoe during the examination. The severe pain would provide a necessary physiological spike at tactical moments in order to fool the examiner.

To join the FBI as a counterintelligence investigator, I needed to receive a top-secret security clearance. And to do that, I needed to pass a polygraph.

Of course, I didn’t have a tack in my shoe during my first examination. The FBI called me into a gloomy room in a nondescript office building sandwiched between a coffee shop and a shoe store. A man in shirtsleeves and a tie—security badge on a lanyard around his neck and a pile of paperwork on his lap—sat me in a chair facing the door. With practiced motions, he fit a thick band across the midpoint of my chest, right at my diaphragm, and clipped sensors onto the fingers of my right hand. A blood-pressure cuff squeezed my upper arm. Numerous wires and cables trailed from the various attachments on my body to a metal box on a side table. Nothing about the situation made me comfortable.

The questions he asked made me recall an initial step in my background investigation—half a year before I ended up strapped in the polygraph chair. One Sunday morning after I first applied to the FBI, a retired agent had shown up unannounced at the town house I shared with three roommates. I was in my early twenties, and when the doorbell rang, I was sitting on the couch with an old friend, recovering after a wild Saturday night. Christian and I had known each other since we were ten. After over a decade of friendship, he knew where I hid my skeletons.

The agent who appeared on that Sunday morning hoped to interview my roommate—a standard part of the background-check process. When he learned that my housemates were out, he pointed toward Christian and said, “Who’s that?”

“My best friend of ten years,” I said.

The agent smiled. “He’ll do.” He looked at me. “Why don’t you go upstairs for a while?”

An hour later, I rejoined Christian on the couch. My old friend answered my impatience with a perplexed face.

“Strange questions,” he said.

“Like what?”

“ ‘Have you ever known Eric to injure or torture small animals or seek their death?’ ”

We both had a chuckle at that one. The next question was about my relationship with money. Was I frugal or a spendthrift? Did I have a gambling problem, or take risks with money, or seem to go through large amounts of it?

No worries there either.

From the B&N Reads Blog

Customer Reviews