Caribbean Tales: Spy on Me

In this story, you will have to suffer through some plot development before you get to the Good Parts. I think you'll find it's worth the wait. Also, please let me emphasize that every aspect of this story is purely fictional.

Shanice was recruited during her senior year in college. It was not hard to understand why; she had a knack for languages, and she was studying several that must have made her interesting, including German and Russian. Plus, she was going to school on an AFROTC scholarship -- it was her ticket out of the 'hood, but it also meant that the government had made an investment in her. Long story short, she had a job with Air Force Intelligence.

The fact that she was considered attractive was probably also a factor. Not that she was being groomed to be the next Mata Hari, but she had found that her looks distracted men and put them off their guard, which is occasionally helpful in intelligence work. Her mixed-race parentage provided her with an ambiguous ethnicity, a medium-brown complexion that could be mistaken for any number of different nationalities.

So she signed on, and underwent extensive training. Some of it was exciting cloak-and-dagger stuff, but much of it was tedious and bureaucratic. It was like going to college all over again, but without the social life -- she didn't have time to make friends outside the organization, and fraternization was discouraged, to put it mildly. It was a highly competitive environment, and the women were a minority, determined to show up the men.

During her last year of training in 2008 she was summoned to Dr. Pearson's office. Pearson was the head of the training facility, a tall man with steel-gray eyes whose military haircut obscured his baldness. "Ms. Dabreo," he said, gesturing toward a chair, "you seem to know your way around a computer. I want to talk to you about Cyberwarfare. The Air Force is preparing to compete with other branches of the defense establishment for the lead role in this emerging area of conflict. We want to give a few new agents some extra courses in this field. Are you interested?"

She told him that she was.

So, for the next 9 months she was increasingly immersed in the techniques of computer security, both how to strengthen it, and how to compromise it. Among other things, she studied the intricacies of Titan Rain, the successful assault on US cyber-security that was originally attributed to the Chinese, but later acknowledged to be of unknown origin. By 2009, Shanice was a qualified field agent.

Oftentimes, being in "the field" meant simply being online, cultivating relationships with shadowy entities whom one recognized by their choice of screen-names but more importantly, elements of their online style. Shanice was sitting in her antiseptic little cubicle somewhere in an anonymous-looking office in Arlington, about to open an email from "Roland." Roland purported to be a cyber-security consultant in the corporate world (as did Shanice.) He stood out because of his obvious competence, and his wit. Shanice was probing to see whether he might have access to software that could be a credible threat to US government computer systems.

"Hey, Rochelle," the email began. "Rochelle" was a name Shanice used for one of her online identities.

The email continued. "Do you remember TR? I think I know who did it. IM me noonish."

Shanice was certain that "TR" meant Titan Rain. She looked at her watch, which read 10:50 AM. She arose and walked down the hall to Pearson's office.

The door was open. Shanice rapped on the door frame, and Pearson looked up from the file he was reading and beckoned her in. "What's up?" he asked.

"I have a contact who claims to know something about Titan Rain. He seems knowledgeable and maybe there is something to it."

Pearson looked unimpressed. This wasn't the first report of this type. "What's his profile? Do we know anything about him?"

"He claims to be a corporate spook. He's smart. Other than that, he's just a screen name. But I have watched his online activity for eight months, and interacted with him for five, and he has demonstrated an in-depth working knowledge of cyber-security measures and countermeasures, including Titan Rain."

"Well..." Pearson gave a perfunctory nod. "Initiate contact. But do it by the book."

"Yes, sir," Shanice replied.

She returned to her desk, and started a file on Roland. She assembled notes she had made on her previous discussions with him, mainly subjective observations and hunches, plus hard copy of emails and chat sessions. She made an initial attempt to trace his IP, but gave up quickly upon the realization that he was a pro and would cover his tracks. Shortly before 12:00 she composed an IM to Roland:

"Hey. What's the story with TR." Then she pushed the "send" button.

After about 30 seconds, a reply appeared. "There are some folks who are selling both offense and defense. Can't say more online."

"What other options do we have?" typed Shanice.

"Face to face," came the reply. Wow, thought Shanice. That was easy. She typed "Where?"

"Check your inbox." Then Roland broke off contact.

Shanice opened the inbox for "Rochelle". There was a message with the subject header "Cyber-Security Conference." She opened the email, and found an advertisement for a conference to be held in two weeks in... Negril, Jamaica.

Shanice froze for a moment. Her father was from Jamaica, and she had visited Granny in Kingston many times as a girl. Could Roland know that? Was he profiling her, just as she was attempting to profile him, only with better success? But upon reflection, it seemed unlikely that Roland would organize a public conference in another country, just based on that knowledge. It was most likely a coincidence. Just the same, Shanice decided to verify the existence of the conference and the organization sponsoring it. After a few minutes on the web, she managed to do all of that, and relaxed a bit. But all this still had to be approved by Pearson.

She made the trip down the hall again. The door was open, but Pearson was on the phone. Then she realized he was concluding his call. He saw her out in the hall, and waved her in as he hung up the phone. "Have a seat," he said.

Shanice sat in the chair facing his desk. "Sir, I believe my contact has Titan Rain for sale."

"How does he want to do it?"

"At a conference, second week of July. In Jamaica."

Pearson's eyebrows went up. He had read her file. "Does your contact know about your family ties?"

"Sir, if he does, he didn't get it from me. The conference sponsor is a legitimate organization. And I'm thinking that if the contact doesn't know I've spent time in Jamaica, it could give me an edge. Sort of a home court advantage."

Pearson thought for a moment. "OK, I'll approve the op. We'll send Kenny and Bruno as backup. But remember... by the book."

"Absolutely, sir." Shanice got up and returned to her cubicle.

Over the next week, she made travel arrangements and registered "Rochelle" for the conference. She met with Kenny and Bruno, two of her colleagues who had completed their training a year ahead of her. They would travel separately and take care of surveillance, plus any unanticipated problems that might arise. The two fellows cracked jokes about a Caribbean vacation. Kenny was an ambitious, straight-arrow type with aviator glasses and sand-colored hair, who seemed like he would have no idea what to do on a vacation. Bruno, on the other hand, was an easy-going Hispanic guy from Los Angeles. Like Shanice, he had come up from a poor neighborhood, and she felt comfortable with him. He was soft-spoken with a sly smile. He mentioned something to Shanice about a "hacker trap" that agency techs were devising to catch Titan Rain, using computer forensics techniques to "reverse hack" intruders.

One week before the conference, Shanice sent an email to Roland: "I'll be there -- how will I know you?"

Four hours later, the reply came: "Dark green suit. Cowboy hat." Well, thought Shanice. Rather flamboyant for a cyber-spook. But then again, North Americans tend to let it all hang out when they visit Jamaica.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Shanice was on board a commercial jet, flying south along the eastern seaboard. She flew coach; the Agency was cheap. Kenny and Bruno had taken a different flight, standard security protocol. They would also stay in a different hotel in Negril, but the Agency had given them a set of secure cell phones that would serve to keep them in contact. She had reviewed everything the Agency had on Titan Rain, and made further efforts to get a profile on Roland, but whoever he was, he was careful. There was no one in the Agency's database that was a clear and convincing match to him. This alone would probably justify the commitment of funds and manpower to this op; even if there were no real link to Titan Rain, it would be useful to have this guy on the radar screen and see whether he turned up elsewhere.

This was not Shanice's first field operation where she was the principal agent, but it was the first time in another country. Plus, the stakes were high. She resolved to go into this with a clear head, and walk away from it victorious.

Her plane landed in Donald Sangster International Airport in Montego Bay shortly before sundown, which comes early in the tropics. Shanice took her time, admiring the facility, before picking up her bags and going through customs. She knew better than to fret about the slow pace of things in Jamaica. But in surprisingly little time, she was outside the terminal, boarding the hotel van for the trip to Negril.

Two hours later the van pulled into the driveway of the Carib Retreat Hotel. Shanice checked in, went up to the second floor, and had a look at her room, which was a clever mix of modern amenities and down-home Jamaican décor. Then she strolled around the hotel. There was no one in a green suit or a cowboy hat. She went back upstairs and out on her room's balcony, which overlooked the Caribbean. She sat there for ten minutes, renewing her acquaintance with the cool night breeze she remembered from her childhood. Then she dialed the cell phone that would connect her with Kenny and Bruno. Kenny answered.

"Hello?"

"Hey. It's Shanice."

"Hey, Shanice. We've already had a look at the conference facilities. There's a spot on the second floor where we can take some pix without being too conspicuous. If your friend shows up, it would be very helpful if you could maneuver him into the restaurant over by the piano, with his back to the windows. Standing near the registration desk, facing the street would be the next best option."

"All right. Let's hope he's cooperative."

"And keep your cell phone with you."

"No problem." Shanice was slightly annoyed that Kenny was reminding her of an obvious security measure. It was typical of him.

"OK, then, happy hunting."

"Thanks."

Shanice went back inside, turned on the TV, watched twenty minutes of a movie she had already seen, and then went to sleep.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

The next morning she saw him right away. Dark green suit, cowboy hat, there didn't seem to be much doubt. He was loitering conveniently near the registration table. Shanice dialed her cell, and got Bruno this time.

"Got your camera fired up?" she asked.

"Roger that," said Bruno.

"Aim it at the registration table," said Shanice, and hung up. She walked around to the hall by the entrance so that she could approach the table from the street side.

As she walked toward the registration area, she called out to him: "Howdy, cowpoke." He turned toward her and grinned broadly. Smile for the camera, she thought. "Rochelle?" he asked.

"That's me." Shanice walked slowly to give her colleagues an unobstructed view for as long as possible. As she walked, she took a long look at Roland. He was cute. He had dark, slightly shaggy hair, and eyes that matched his suit. He looked to be about six feet tall, and a healthy specimen. He appeared to be assessing her, as well, and Shanice realized that walking slowly had put a little swing in her hips. Fine, she thought. If he likes what he sees, his guard will be down, just a little.

He offered her his hand. "Have you registered yet?" he asked. He had an accent which she was trying to recognize. It sounded vaguely eastern European, but it was probably a composite of five or six languages.

"I was just about to do it," she replied.

"I have already made my registration," said Roland. He grinned engagingly and waited while Shanice filled out her paperwork. Then the two of them entered the conference hall.

The first presentation was a panel discussion on cybersecurity for industrial control systems. It was pretty rudimentary stuff. Shanice saw Roland stifle a yawn in the middle of a presentation, and he grinned at her. She grinned back. Without much small talk, they were enjoying the camaraderie of fellow IT professionals.

Toward the end of the panel, Shanice excused herself to use the restroom. As she left the hall, she felt her cell phone vibrate. It was Bruno. Good, she thought, my guardian angels are watching over me. "Hey, Shanice," said Bruno.

"Hey. How's it going?"

"The photos could be better. The cowboy hat is a problem. Could you get him to take it off?"

"I could try. I'll see if I can get him into the restaurant. I think he has enough class to take the hat off when he eats."

"OK, knock 'em dead, girl."

"Roger that," said Shanice.

When Shanice returned to the hall, the session was breaking up. She walked up to Roland, who flashed his grin again. "Roland," she asked, "have you ever tasted ginger beer?"

"Does it taste like ginger ale?"

Shanice's laughter came in a short melodious burst. "No, not really. It's more intense."

"OK, let's try some," said Roland.

Shanice led him toward the restaurant at a rapid clip. She was thinking that, with the session over, it would fill up quickly, and she wanted to be sure to get the right table. They made it to the restaurant ahead of the herd, and she guided Roland to the back by the piano, taking the seat facing the windows so that Roland would have to face the rest of the hotel. So far, so good, thought Shanice. Now take off your hat. Roland smiled, as if acknowledging her unspoken request, and laid his had on the table. Smile for the camera, she thought again. A waitress approached, and Shanice ordered two ginger beers.

After the waitress departed, Roland spoke. "You realize, of course, that we cannot speak of specifics here."

"Of course not," said Shanice.

"But I want to make sure you understand that this involves a large amount of money."

"Certainly."

"You have a large amount of money?"

"No, but my clients can afford it."

"What sort of clients do you work for?"

Shanice smiled and wagged her index finger to and fro. "The kind that can afford it."

Roland smiled back. "OK," he said. "Tomorrow we can talk about this. Somewhere else."

"Where did you have in mind?"

"Someplace where there are no small devices that listen. On the beach. Seven Mile Beach."

"All right," replied Shanice.

"There will be noise, and no place to hide anything. No bathing suits."

At this moment the waitress arrived with the ginger beers. Shanice and Roland were thirsty, and they each took a long drink. Roland's eyes bulged a little. "The taste is very strong," he gasped.

"Yes, it is," said Shanice with a smile. "But you'll get used to it."

"You have tasted it before."

"Yes," she said. She paused. "Did you say no bathing suits?"

"Tomorrow is July 14. National Nude Day. No one will wear suits on Seven Mile Beach." He saw that Shanice looked perplexed. "Is that a problem for you?"

"You're kidding, right?" said Shanice.

Roland shook his head. "It is important negotiation. We need extra security." He smiled ironically, or at least it seemed ironic. Maybe it was mocking, or flirtatious. Shanice was trying simultaneously to read him and to decide how to handle this situation. And, she realized, she liked his smile. His eyes were easier to see without the cowboy hat. They were a sort of jade green. He had a light, European complexion and an aquiline nose. Roland continued, "There is much money involved in this. It is necessary to always change security measures." Shanice nodded skeptically. "I think you are a nice woman, but we know very little about each other. Forgive me that it is necessary to be careful."

Shanice looked doubtful. "I normally do business with my clothes on."

"We don't have to do business. Maybe I find someone else that wants to do business."

"My clients are very interested in what we discussed."

"OK then, no problem, right? We celebrate National Nude Day with a thousand other tourists, and we talk business then."

Shanice swallowed, then nodded. She thought to herself that Pearson had said "by the book." She didn't recall reading about this scenario in the book. She put on her game face. "So. When and where?"

Roland handed her a folded sheet of paper. She opened it and saw a map, depicting a section of Seven Mile Beach with helpful landmarks indicated, including a drawing of an oddly bent palm tree. "One P.M., OK?"

"One it is," replied Shanice.

"OK, Rochelle, I'll see you tomorrow." He put his cowboy hat back on, grinned, tipped the hat, and walked out of the restaurant. Shanice watched him recede. She realized that she felt attracted to him. In college she had dated mainly black guys, and since college... nobody. But there was something very appealing about this guy, with his shaggy hair and sparkling green eyes. She brought herself up short. This is an unhelpful distraction, is what it is.

Shanice sat in on the next conference session for a while, but it was all material she had seen before at the Air Force training facility. She left early to go out and get a meal. As she left the hall, her cell phone rang. Bruno was on the line.

"How's it goin', Shanice?"

"Well... the good news is that we have an appointment tomorrow to talk business."

"We've got some news, too, and it ain't good."

"Oh?" Shanice walked out the hotel doors onto the street, seeking a more discreet environment in which to talk. Negril in the daytime looked very rustic. There were gaily painted buildings, some with new paint, some with old, interspersed with palm trees. She walked along the shoulder of the road, as an occasional car or minibus beeped in warning or greeting.

"We've got facial recognition on Roland. Thanks for those shots in the restaurant, by the way. His real name, or at least one of his real names, is Adam Masek. The intel we have links him to the Mossad."

"Is that a problem? I thought Israel was a close ally."

"Well, yes and no. Do you remember Jonathan Pollard?"

"He was a little before my time. I know he was convicted of spying for Israel."

"But a lot of the material he gave the Israelis was sold to the Soviets within days."

"Ouch. But there are no Soviets now."

"Yeah, things are complicated in other ways now. I can tell you that Dr. Pearson is suddenly a lot more interested in this op. We need to find out as much as we can about who runs this guy."

"There's one thing I can tell you,' said Shanice with a bit of trepidation. "He's very paranoid about security. He's worried about bugs. He insists that we meet on a nude beach."

"Give me a break," said Bruno. Then, with a trace of mockery, "Are you sure he's not just trying to hook up?"

"I don't think that's allowed on the beach here. Just nudity."

"Hang on a second --" Shanice heard Bruno relaying this information to Kenny, who snickered audibly. Bruno came back on the line. "You realize that we've got to take surveillance photos, right?"

Shanice sighed. "Right. Just keep it professional."