The Spy Who Couldn't Spell

by Yudhijit Bhattacharjee

  With the first package unearthed, Carr felt a huge sense of relief. The agents led Regan on through the forest to the second of the two locations he had chosen in that part of the park. Here, too, Regan was able to remember where he’d buried the package. He also recalled now, he told Carr, that for many of the packages, he’d measured the distance of the package not from the tree marked with the nail, as had been assumed, but rather from a second tree that stood directly across from the first, in the direction that the nail pointed at. He had created the offset to add a second layer of security to his hiding scheme, once again not realizing that he could forget this important detail. As Carr and the others would find out, Regan’s execution of the scheme, too, had been far less than perfect. In some instances, he had failed to point the nail in the right direction, which made it a challenge to identify the second tree correctly.

  Sitting down at a picnic table, the agents opened the second package and found a handful of VHS tapes. In them, Regan had copied the contents of classified training videos checked out from the library he once maintained for his division at the NRO. When the agents unfolded the package wrapping, they discovered in one of the inner layers a yellow Post-it note that had Regan’s name and extension number on it. Despite all of the meticulous planning to remain untraceable, he had left behind what Carr would later refer to, in the driest of understatements, as a “clue.”

  Reeser couldn’t resist joking about it then and there.

  “Brian, you left a sticky in here with your name on it,” he remarked.

  “I did?” Regan asked, his tone flat as usual.

  “Yeah,” Reeser said, chuckling. “The only thing missing from the note was a ‘Please Return To.’”

  • • •

  Two weeks later, on June 11, the FBI brought Regan out to Patapsco a second time. Reeser, curious to know more about Regan’s life, sat with him in the back of the SUV. Carr sat in the front, in the passenger seat. Unlike Reeser, he wasn’t keen to chitchat with Regan, even though he was impressed by and grateful for Regan’s savant-like visual memory. Despite reaching the end of the investigation, he couldn’t help feeling angry toward Regan for what the former master sergeant had done.

  The SUV left the prison and headed for the state park, the SWAT team following in a second vehicle. Initially unresponsive to Reeser’s attempts at getting to know him, Regan eventually opened up enough to give Reeser a brief glimpse into his life and the circumstances that had led him to plot espionage. His mounting burden of debt and the stress of raising four kids on a single modest income in one of the most expensive metropolitan areas of the country—compounded by the misery of an eighty-mile commute to work and back every day—had put him over the edge, he explained. He simply needed the money.

  The vehicles entered Patapsco and parked in a meadow. Regan had buried two packages in the nearby area—one in a low-lying glade and the other on a neighboring hillside. The group walked to the lower site, which was lush with tall grass. Regan, wearing a blue Windbreaker that belonged to Carr, squinted in the bright midmorning sun. There weren’t many landmarks in the clearing where the package was supposed to be, and he struggled to recall where he’d dug in relation to the marked tree in the vicinity. He was confused about which tree he’d measured the distance from; he wasn’t certain if he had, in fact, used the double-tree system for this package. He provided his best guess, and the agents dug down a couple of feet there but couldn’t find anything. Seeing how soft the soil was at this site reminded Regan that he’d buried the package deeper in the ground. Carr was confident that they’d find the package with some more digging and decided that they could return to it later.

  The agents took Regan to the hillside, making their way up through some dense woods. It would have been hard for Regan to keep his balance walking uphill with his wrists handcuffed together, and so Carr freed Regan’s left hand and cuffed the other to a belly chain around his waist. The sun was getting hotter, the air more humid. When they’d climbed up to the site, everybody took a moment to catch their breath.

  Regan looked around at the trees on the slope.

  “OK, now, let’s recap what we have here,” Carr said, leaning against a tree as he spoke. He went over some of the details that Regan had shared during the debriefings.

  “You climbed up, you were out of breath, you laid your tarp out, you were digging,” Carr said. Regan had described bringing a tarpaulin sheet with him to pack up any dirt left over after burying a package.

  Regan nodded, still catching his breath.

  “You remember there was some slope, right?” Carr asked. “Because the dirt was sliding off your tarp, correct?”

  Regan nodded again, vigorously. He remembered this quite well.

  Carr began walking from the tree he was leaning on. Regan followed him, treading over dry leaves that layered the ground. “This is the slope right here,” he said, when they’d walked a few paces.

  “The nails are right here,” Reeser said, standing higher up by the reference tree.

  “Yeah,” Regan said, continuing to walk farther down. “The dirt was rolling downhill.” He motioned with his free hand to show the slide.

  “This looks about the slope you were working off?” Carr asked.

  “Yeah,” Regan said, looking up.

  “What was the distance here, Marc?” Carr asked, wanting to know the number of feet Regan had put down for this package.

  “Six feet,” Reeser replied.

  Regan looked up at the marked tree and the one across from it, taking a moment to estimate where that distance would be, if measured from the second tree, as he recalled having done.

  “That would put you back here,” he told Carr, pointing at the ground a couple of feet from where he stood. With his foot, he removed the leaves from the spot.

  A SWAT team member named R. J. Porath who had been watching impatiently grabbed a shovel and started digging. Shortly after, Reeser, looking into the expanding hole, caught sight of the package.

  “That’s it,” Reeser said.

  “Look what you did, Brian,” Carr said, admiringly.

  Regan gave a nod of acknowledgment while Porath continued digging the dirt out around the package.

  “Does this help with any of the other sites?” an agent asked.

  “Oh yeah,” Carr replied. “This validates the theory of the second tree.”

  Porath pulled the package out and heaved it onto the side. It was a large Rubbermaid container stuffed with documents.

  “Look familiar?” Reeser asked, turning to Regan, who stood next to a tree, his hand resting on the trunk.

  Regan nodded, looking downcast. For the first time, his characteristic neutral expression seemed to have been replaced by a profound sadness.

  “Is there going to be just one there?” somebody asked.

  Regan nodded again, with pursed lips.

  It was past noon. As had been the case on their last excursion, Carr was under strict instructions from the jail authorities to bring Regan back to prison at the earliest. The agents hiked down the hill to the meadow where the SUVs were parked. The group exited the park and stopped for lunch at a McDonald’s.

  “I got this, Brian,” Carr said.

  His offer to buy Regan’s meal evoked a chuckle from Reeser, who found it comical that Carr had so magnanimously stated the obvious. After all, Regan—sitting in handcuffs—was clearly in no position to pay.

  “Big spender, huh?” Reeser joked. Carr knew he was going to be teased about it for years to come. He turned to look at Regan.

  “What do you want?” he asked.

  “I want a quarter pounder with cheese, with no onions,” Regan said. “I want mustard on it. No mayo.” He was about to add more detail to the order when Reeser interrupted him.

  “Brian, this is not a five-star restaurant,” Reeser said. “Why don’t you jus
t get a quarter pounder and be done with it?”

  “Well, I don’t get it that often,” Regan replied. “So I want to get what I want.”

  Carr and Reeser went into the restaurant, asking a couple of SWAT team members to stay with Regan in the vehicle. Carr returned with a cheeseburger for Regan, which he chowed down in a few quick bites. With encouragement from the SWAT team members, who suggested he take advantage of the opportunity, Regan ended up eating a couple more burgers. Not long after, Carr handed him over to the guards at the Alexandria jail, where he changed into his prison clothes before being escorted back to his cell. This was not the life he had imagined.

  • • •

  Brian Regan was a pioneer, the first spy to exploit digital access to American defense secrets on a massive scale. His actions of pilfering classified information from the intelligence community’s servers foreshadowed the handiwork of Edward Snowden, the NSA contractor who downloaded hundreds of thousands of files from the Department of Defense and the NSA, and U.S. Army private Chelsea (Bradley) Manning, who lip-synched to Lady Gaga while exfiltrating more than seven hundred thousand pages of classified and sensitive information stored on government computers. If the intelligence community had done a better job of understanding the vulnerabilities laid bare by Regan’s theft, and applied those lessons to fortify its digital networks from insider threats, the devastating leaks by Snowden and Manning—driven though they were by supposedly nobler motivations than Regan’s—could have been prevented. (Whether it would have been desirable to prevent Snowden and Manning from making the disclosures is a different debate.)

  This is not to say that the NRO and the FBI didn’t delve deeper into Regan’s crime after all the buried secrets had been recovered. Through the end of the summer and the early fall of 2003, Carr and other investigators, including the NRO’s Bob Rice, interviewed Regan over dozens of hours to learn precisely how he’d gone about planning and executing his espionage. The answers he provided in these debriefing sessions helped them fill in the details of the picture they had pieced together during the course of the investigation. He confirmed that he had meticulously studied espionage cases on Intelink to come up with what he hoped would be a foolproof plan. It was shocking for Rice and other NRO officials to hear Regan describe the ridiculous ease with which he was able to print and copy a vast number of classified documents. Even more embarrassing for the agency—which spends hundreds of millions every year on security—was Regan’s account of how he’d walked out of the NRO building, day after day, with classified materials hidden in his gym bag. Somebody stealing books from a library could have been at greater risk of getting caught.

  Regan explained how and why his plan had evolved over time. By the early spring of 2001, he had abandoned the hope that the Libyans would ever respond to his offer: that’s why he never saw the ad the FBI had placed in the Washington Post’s classified section. When he traveled to Europe in June and failed to market himself despite meeting with the Libyans face-to-face, he decided that he needed to bring along a sample of recently collected U.S. intelligence in order to be taken seriously. He also visited a handful of Swiss banks on the June trip, hoping to get himself a locker in which to stash the proceeds. The banks told him that he would first need to open an account, which would require a significant deposit. Regan hoped that the Iraqi and Chinese intelligence officials he expected to make contact with in Europe on the next trip would give him enough money in cash for the sample information—the missile coordinates, the classified course descriptions—to help him open a Swiss bank account. In case he still had trouble getting a locker, he planned to hide the money, which explained why he packed a GPS and a shovel and packing tape for the trip that was prevented by the FBI.

  For Regan to think that he wouldn’t be viewed with suspicion when he walked into those embassies was naïve but understandable. There was a grain of truth in his defense lawyer’s characterization of his scheme as a “spy fantasy.” Unlike earlier traitors such as the CIA’s Aldrich Ames and Jim Nicholson, whose experience in spying on behalf of the United States and liaising with foreign intelligence officials gave them the knowledge and cover needed to conduct nefarious transactions with the enemy, Regan had never had any occasion to gain firsthand experience with the spying business. He was a dilettante, teaching himself the tradecraft by relying on books and movies.

  Even a lot of the cryptography Regan used was self-taught. He remembered very little from the basic cryptanalysis course he had taken early in his career. When Olson interviewed him about the codes after the packages had been dug up, Regan told him that his enciphering had been driven both by his concern for security and by his paranoia about forgetting the key, which had happened to him once when he encoded the name and number of an old girlfriend. He came up with the idea of using his yearbook for a key for the Maryland coordinates after he saw the movie Manhunter, in which Hannibal Lecter relies on a book code to communicate with the killer known as the Tooth Fairy. Months later, while encrypting the Virginia coordinates, he decided it was better to use a key that he could carry with him at all times without its looking suspicious—hence the choice of the three NRO phone lists. For somebody with only a rudimentary knowledge of cryptography, these steps toward improving security demonstrated remarkable creativity.

  But in inventing encryption schemes of his own, he had made things too complex—not just for the FBI but also for himself. Olson pointed out to him that there was no need to have added the second layer of encryption he had—using those number tables—in both the Virginia and the Maryland codes.

  “You could have accomplished the same thing by using a one-time pad,” Olson said, referring to a well-known and relatively simple encryption technique involving a random key.

  “What’s a onetime pad?” Regan asked him, betraying his ignorance of cryptographic systems.

  The deeper the investigators delved into Regan’s treason, the more they were amazed by the mismatch between his outward persona and his inner self. Reading the dozens of handwritten notes found in Regan’s car and house, Carr and his fellow agents could have been forgiven for viewing him as a clueless dope. They chuckled at his reminders to pack “moose” for his thinning hair before going on trips. It baffled them to see that he needed to write instructions for himself on how to commute to work. They joked about his confidence in his investment acumen, which they greatly doubted when they looked at his online stock trades and read his nuggets of financial wisdom, one being that he would put all his money into gold. “Brian’s got another investment strategy,” they joked. “Buy low, sell high.”

  Analyzing his plot, however, revealed a cunning and diabolical mind. Regan’s idea of creating preloaded dead drops to be sold later, after a buyer had been found, was a brilliant one. Although it would seem obvious in hindsight, his exploitation of digital access to classified information was pioneering. Investigators had to concede that they might never have found the buried packages without his help.

  Yet, despite the brilliance of his plan, Regan’s propensity for blunders all but guaranteed his failure as a spy. At nearly every step in the execution, he tended to make some kind of last-minute error, inevitably and unerringly, similarly to how he couldn’t avoid misspelling words. Despite knowing that spellings weren’t his strong suit, he failed to correct them before sending out his offer to foreign intelligence services, which likely made him look like a potential liability to whoever’s desk the offer landed on. When he rented the storage unit near Richmond to store the hidden documents, the false name he used for the rental was “Patrick Regan”—something that could have easily led investigators to him, had they stumbled upon it. Summing up this proclivity to be brilliant for part of the way and then take a sudden left turn to stupidity, Reeser named Regan “Mr. Eighty Percent.”

  Regan’s flaws in execution might have been trivial compared to his errors in judgment. Where others might have gone to a financial counselor t
o find a way out of debt, or sought help from friends, he dreamed up the most risky solution imaginable. Once caught, he grossly miscalculated the leverage he had in his negotiations with the U.S. government: despite being faced with the death penalty, he deluded himself into thinking that he would be able to bargain his way out using the packages he had buried. As if that wasn’t bad enough, he undermined his position further by involving Anette in a complex plan to cover up his crime, leaving her at risk of being prosecuted.

  Together, these decisions amounted to nothing short of legal hara-kiri. They seem to have been the product of a person hell-bent on proving others wrong, no matter how devastating the cost to himself. If Regan’s perverse bid for riches and respect was partly driven by society’s underestimation of his intelligence, in the end, he appeared to have hammered the nails into his coffin by overestimating his intelligence.

  In March 2008, interviewed by NRO officials in prison, Regan seemed to have gained the sort of clarity that is bestowed only by the passage of time. He said he had lost touch with reality when he began plotting treason and had talked himself into thinking, right up to the trial, that he wouldn’t get convicted. Even though he didn’t think he deserved life in prison, he admitted that he had sealed his fate by not accepting the plea agreement offered to him.

  “If I had understood that the financial situation could be corrected somehow, I wouldn’t have gone off the deep end,” he said in another interview with the NRO a few years later. “I felt the only option I had was to sell something.” He’d chosen countries in the Middle East, he explained, because they had “oil money” and weren’t very sophisticated in their intelligence gathering. “My goal was never to bring harm to the United States. I didn’t want anybody to get killed. I just needed the money. I thought I could get some cash to solve my problems.” All his life, he had strived to escape his doltish image, but it had chased him like a shadow until the two had tragically become one.