How America Lost Its Secrets

by Edward Jay Epstein

  Under extraordinary circumstances, even the minimum requirements might be waived if the applicant had a distinguished military career and an honorable discharge. Snowden, however, did not complete his military training at Fort Benning and received only an administrative discharge.

  The CIA, to be sure, had needed computer-savvy recruits to service its expanding array of computer systems since 1990. By 2006, however, there was no shortage of fully qualified applicants for IT jobs who met the CIA’s minimum standards. Most of them had university course records, work experience at IT companies, computer science training certificates from technical schools, and other such credentials. The CIA, like the NSA, also obtained technicians with special skills for IT jobs from outside contractors. So it had no need for employing a twenty-two-year-old dropout who did not meet its requisites. According to Tyler Drumheller, a former CIA station chief in Europe, the only plausible way that Snowden, with no qualifications, was allowed to jump the queue was that “he had some pull.”

  In 2006, Snowden’s grandfather, who had attained the rank of rear admiral, was certainly well connected in the intelligence world. After twenty years’ service in the Coast Guard, Barrett had joined an interagency task force in 1998, which included top executives from the CIA, the FBI, and the Drug Enforcement Administration. It had been set up to monitor any gaps in the U.S. embargo on Cuba, and Barrett, as one of its leaders, was in constant liaison with the CIA. By 2004, he had joined the FBI as the section head of its aviation and special operations. In this capacity, he supervised the joint CIA-FBI interrogation of the prisoners in the Guantánamo base in Cuba, which involved him in the rendition program for terrorists.

  Barrett could certainly have played a role in furthering his only grandson’s employment. The CIA, however, has not disclosed any information about who, if anyone, recommended Snowden. All that is known is that in 2006 the CIA waived its minimum requirements for him.

  Later Snowden pointed out from Moscow that in 2006 the federal government employed his entire family. His father was serving in the Coast Guard; his mother was an administrative clerk for the federal court in Maryland; his sister was a research director at the Federal Judicial Center; and Admiral Barrett was still a top executive at the FBI. In a sense, Snowden had entered the family business.

  CHAPTER 2

  Secret Agent

  Sure, a whistleblower could use these [NSA computer vulnerabilities], but so could a spy.

  —EDWARD SNOWDEN, Moscow, 2014

  THE SUDDEN TRANSFORMATION of Snowden in 2006 from a night watchman on a university campus to an employee for the CIA provided him with a powerful new identity and one much closer to the avatars he adopted for his fantasy games. It was burnished so deeply in his self-image that he cited it eight years later, in exaggerated fashion, in Moscow. When Brian Williams, then an NBC anchorman, began an hour-long television interview with Snowden in 2014 by saying, “It seems to me spies probably look a lot more like Ed Snowden and a lot less like James Bond these days,” Snowden approvingly smiled and told him, “I was trained as a spy in sort of the traditional sense of the word.” Snowden further confirmed his interviewer’s point, stating, “I lived and worked undercover overseas—pretending to work in a job that I’m not [in]—and even being assigned a name that was not mine.”

  In reality, Snowden’s employment at the CIA was far more prosaic. When he joined the CIA, he did not have the required experience in maintaining secret communication systems, so the CIA sent him to its information technology school for six months to train as a communications officer, not a spy. After completing his training, he was dispatched to the CIA station in Geneva. He worked there for the next two years as one of dozens of information technologists servicing the CIA’s communication channels in Switzerland. He was stationed there, according to Swiss registry records, under his own name from March 2007 to February 2009. He was identified as a U.S. State Department employee in Geneva because Switzerland does not allow any intelligence officers to operate in its country. Officially, he was attached to the permanent U.S. mission to the United Nations, which employed hundreds of U.S. government functionaries in Switzerland. It was a thin cover; the Swiss government was aware that the CIA maintained its base in Geneva and posted its employees at the U.S. mission.

  Although Snowden would claim in a video he made in Hong Kong that he had served as a “senior adviser for the Central Intelligence Agency,” he was merely a telecommunications support officer, or TSO in CIA parlance, which was a junior-level job at the CIA. He worked as part of a team of information technologists under the supervision of senior CIA officers, according to a former CIA officer in Geneva. The job of these TSOs was to protect the security of the CIA’s computer systems through which the CIA station in Geneva sent and received its secret communications.

  As far as is known, Snowden made very few friends at the eight-hundred-person mission. The only person to have publicly reported knowing him in Geneva during this period is Mavanee Anderson, a young and attractive summer intern at the U.S. mission from May to August 2007. She described befriending Snowden, who, according to her, said that he was in the CIA and also demonstrated to her his martial arts skills. She later recalled in interviews that he was “a bit” prone to brooding and voiced growing dissatisfaction with the CIA.

  The job in Geneva did have its benefits, however. It provided him with a generous housing and travel allowance. In many ways, it was the “cushy government job” he had said he was seeking in his Internet posts. He rented a four-room apartment and had his girlfriend, Lindsay Mills, now twenty-one, join him there.

  According to his posts on the Ars Technica website, he took full advantage of his compensation to live the high life. He gambled on financial developments by buying and selling options, which are contracts that allow speculators to bet on the directions of the market without buying the actual stocks, bonds, or commodities. He also bought a BMW sports car on which, he wrote, he disabled the speed control so he could exceed the legal limit. He described in his posts racing motorcycles in Italy and traveling around Germany with an Estonian rock star (whom he did not further identify). He also continued his avatar life in Internet gaming; the alias he chose for that was Wolfking Awesomefox. He also indulged in a fantasy gun sport called Airsoft, a variation of paintball, in which participants used realistic-looking pistols to splatter each other with paint.

  Snowden’s good fortune came to an abrupt end in 2008. He suffered a massive loss in his options speculations. He wrote in a post that he had “lost $20,000 in October [2008] alone,” a sum that represented almost a third of his annual salary. He blamed the U.S. financial system, posting on Ars Technica that Ben Bernanke, the Federal Reserve chairman, was a “cockbag.” He also bet against any further rise in the stock market index, asking a user with whom he was chatting on the Internet in December 2008 to “pray” for a collapse of stock prices. When his correspondent asked him why he wanted him to pray for a decline, Snowden responded, “Because then I’ll be filthy fucking rich.” But Snowden lost this bet.

  Snowden lashed out at others on the Internet over these setbacks. He termed those who questioned his financial judgment “fucking retards.” As with other setbacks, he blamed them on government officials in Ars Technica posts. Because the CIA was engaged in 2008 in highly sensitive operations to gather banking data in Switzerland—one of which Snowden later disclosed to The Guardian—any Internet discussion by a CIA employee of financial losses could serve as a beacon to an adversary intelligence service on the prowl for a source. If any party was looking for disgruntled U.S. employees, Snowden’s Internet chatter about bad choices in gambling could have aroused its interest.

  That Snowden used his TrueHooHa alias for these Internet postings would not prevent a sophisticated espionage organization from quickly uncovering his true identity. He was listed by his true name on the roster of the U.S. mission to the UN. By consulting personnel records, one would further discover that he did not actually
work for the State Department. Because it was no secret that the U.S. mission in Geneva housed the CIA station for all of Switzerland, any outsider would think it probable that this brittle gambler who played the options market worked for the CIA.

  Even though it cannot be precluded that Snowden was spotted in Geneva by another intelligence service, there is no evidence, at least that I know of, to suggest that he was approached by one. Nor is there reason to believe that if he had been contacted by a foreign service in 2008, he would have responded positively. Despite his indiscreet posting about his outside activities, he apparently still respected the boundaries of secrecy that had been clearly defined in the oath he had taken at the CIA. For example, after The New York Times published an article revealing secret American intelligence activities in Iran on January 11, 2009, Snowden railed against the newspaper on the Internet under his TrueHooHa alias. He wrote, “This shit is classified for a reason….It’s because this shit won’t work if Iran knows what we are doing.” He clearly recognized that revealing intelligence sources was extremely damaging. As for the Times, he said, “Hopefully they’ll finally go bankrupt this year.” When another Internet user asked him if it was unethical to release national security secrets, he answered, “YEEEEE­EEEEE­S.”

  As with every CIA officer, Snowden had to undergo a two-year evaluation and take a routine polygraph test. It was then, in December 2008, that his superior at the CIA placed a “derog” in his file, the CIA’s shorthand for a derogatory comment, in an unfavorable evaluation. The reason remains somewhat murky. According to a New York Times story by the veteran intelligence reporter Eric Schmitt, Snowden’s superior had suspected that Snowden “was trying to break into classified computer files to which he was not authorized to have access.” Schmitt evidently had well-placed sources in the CIA. He said that he interviewed two senior American officials who were familiar with the case. According to what they told Schmitt, the CIA superior had decided to “send Snowden home.” Officially, however, according to a reply by a CIA public affairs officer to the Times, Snowden had not been fired or accused of attempting to “break into classified computer files to which he did not have authorized access.”

  A former CIA officer who had also been at the U.S. mission in Geneva explained the discrepancy to me. He said that the spin the CIA put on the story was “necessary containment.” After the Snowden breach occurred in June 2013, the CIA had a problem that could, as he put it, “blow up in its face.” If Snowden had been fired but allowed to keep his security clearance in 2009, the CIA’s incompetence could be partly blamed for the NSA’s subsequent employment of him. If he had broken into a computer to which he was not authorized, he should have been fired if not arrested.

  What this spin glossed over, according to this former CIA officer, is the part about Snowden’s behavior that concerned his superior. Technically, Snowden, as a CIA communications officer, was authorized to use the computer system. The problem was that Snowden had deliberately misused it by adding code to it. This code could have compromised the security of the CIA’s “live system.” So while what the CIA public affairs officer quoted in the Times story said was correct, it clouded the issue.

  During his time in Geneva, Snowden had received no promotions or commendations for his work. He was threatened with a punitive investigation unless he agreed to quietly resign from the CIA. “It was not a stellar career,” Drumheller, the former CIA station chief, told me in 2014.

  Snowden blamed his career-ending “derog” on an “e-mail spat” with a superior. From Moscow, he wrote to James Risen of the Times that his superior officer ordered him not “to rock the boat.” Further, he complained that the technical team at the CIA station in Geneva had “brushed him off,” even though he had a legitimate grievance. When he complained about a flaw in the computer system, he said that his superior took vengeance on him. He said he added the code to the system to prove he was right. He attributed the “derog” in his file to the incompetence, blindness, and errors of his superiors. According to Snowden, he was a victim. This would not be the last time he faulted superiors for their supposed incompetence. He would later say that the NSA experts who examined the documents that he had stolen were “totally incapable.”

  In any case, in February 2009, Snowden not only had a career-damaging “derog” in his file but faced an internal investigation of his suspicious computer activities. According to Drumheller, such an internal investigation would not be undertaken lightly or because of an “e-mail spat.” He said that such an investigation was “a big deal” involving the CIA Office of Security in Washington and possibly the FBI. It would also result in the temporary suspension of Snowden’s security clearance. This left Snowden with little real choice. If he wanted to avoid that investigation, he had to resign from the CIA, which he did in February 2009. That was the end of the security investigation.

  He was clearly bitter, posting on Ars Technica on January 10, 2009, “Obama just appointed a fucking POLITICIAN to run the CIA!” (He was referring to Leon Panetta, President Clinton’s former chief of staff.) Snowden attributed the origins of his antipathy to U.S. intelligence to his 2007–9 experiences in the CIA. He later told Vanity Fair that the 2009 incident in the CIA convinced him that working “through the system would lead only to reprisals.”

  Snowden, if not yet a ticking time bomb, was certainly a disgruntled intelligence worker before he ever got to the NSA.

  CHAPTER 3

  Contractor

  Private contractors don’t clear employees. The government does.

  —ADMIRAL MICHAEL MCCONNELL,

  former vice-chairman, Booz Allen Hamilton

  SNOWDEN, aged twenty-five, returned from Europe and moved into his mother’s condo. Not only was he unemployed now, having resigned from the CIA, but his financial state had been hurt by the huge losses he had suffered playing the options market in Geneva and by the fact that he did not qualify for any CIA benefits. His vision of himself as a secret agent, the unstoppable Wolfking Awesomefox, might have also suffered. According to the narrative he later supplied to The Guardian, he had become deeply concerned about the immoral way in which the CIA conducted its intelligence operations in Switzerland.

  “Much of what I saw in Geneva really disillusioned me about how my government functions and what its impact is in the world. I realized that I was part of something that was doing far more harm than good,” Snowden told The Guardian. By way of example, he said he learned that the CIA had gotten a Swiss banker drunk enough to be arrested when he drove so the CIA could compromise him. Snowden, who did not drink himself, was appalled at this ploy. Despite his growing antagonism toward the U.S. government, he had not given up on, if not becoming a secret agent, working in the netherworld of secret intelligence.

  There was still a back door through which he could reenter the spy world. Private corporations hired civilian technicians to work for spy agencies as independent contractors. By 2009, the CIA, the NSA, and other U.S. intelligence services had outsourced much of the job of maintaining and upgrading their computer systems to these private companies. They supplied the NSA with most of its system administrators and other information technology workers. This arrangement allowed the NSA to effectively bypass budget limits and other restrictions limiting how many NSA technicians it could recruit. Instead of being on the NSA’s own payroll, these people nominally worked for, and received their paychecks from, private employers. In fact, many of these outside contractors worked full-time for the NSA.

  Snowden applied in April 2009 to one of these private companies, a subsidiary of the Dell computer company. To diversify out of manufacturing computers, Dell had recently gone into the business of managing government computer systems for the NSA and other intelligence services. As a leading specialist in the field of corporate cyber security, Dell had no problem obtaining sizable contracts from the NSA’s Technology Directorate. In 2008, the NSA had in effect outsourced to Dell the task of reorganizing the backup systems at its
regional bases. Dell had to find thousands of independent contractors to work at these bases. In 2009, it was seeking to fill positions at the NSA’s regional base in Japan, and Snowden applied. Relocating would be no issue for him because he had a longtime interest in going to Japan.

  He had little problem obtaining the job. He had a single compelling qualification: like all other CIA officers, he had been given a top secret clearance. For an outside contractor such as Dell, such a security clearance was pure gold. If a potential recruit lacked it, Dell needed to wait for a time-consuming background check that would have to be conducted before it could deploy him or her at the NSA. If a recruit already had the clearance, as Snowden did, he could begin working immediately.

  Snowden still had his security clearance, despite his highly problematic exit from the CIA, because the agency had instituted a policy a few years earlier that allowed voluntarily retiring CIA officers to keep their clearance for two years after they left. This “free pass,” as one former CIA officer called the two-year grace period, had been intended to make it easier for retiring officers to find jobs in parts of the defense industry. This accommodation, in turn, made it easier for the CIA to downsize to meet its budget.