Operation Venceremos: Undercover in Cuba

By John White Jr.

In the beginning of the Cuban Revolution the CIA sends JOHN MICHAELS to Havana as an undercover field officer. His assignment . . . find out what Fidel Castro is up to and where he is taking the country. John’s cover is working for the Ministry of Culture as a leading dancer in the Cuban National Ballet Company. His covert mission is part of OPERATION VENCEREMOS, an ingenious plan designed to precipitate the collapse of international communism.

John takes readers through events prior to his arrival in Cuba, including his CIA recruitment; instruction in espionage tradecraft; black ops training; and undercover field-officer preparation at the Agency’s top-secret facility in Virginia, and his unique world of classical ballet training and performance. While dancing in Hollywood, John falls in love with Margarita Guzman, a beautiful Cuban ballerina, and gets invited to join the Cuban National Ballet Company. This provides a perfect cover and a plausible reason for being in Cuba.

Readers will enjoy John’s adventures in Cuba as he arranges the defection of a Russian collaborator, gathers critical intelligence confirming the arrival to Cuba of thousands of Soviet troops and vast quantities of sophisticated weaponry, and the daring escape across the Florida Straits with Margarita.

• Language: English
• Publisher: Gatekeeper Press
• Release date: Mar 8, 2022
• ISBN: 9781662911354

Book preview

CHAPTER ONE

Coppelia

Shortly after graduating from Occidental College in 1957, John Michaels received a telegram from Washington, DC, informing him that his application for employment with the Central Intelligence Agency had been approved. It was signed by Allen W. Dulles, director. The cable said that John would receive instructions about when and where to report sometime within the next sixty days. He was also reminded that all communications between him and the Agency were strictly confidential and not to be discussed with anyone.

John felt that he was joining a unique unit of national defenders, and it merited bragging rights. It would be a struggle to keep the secret. But he dutifully bit his tongue and waited patiently for instructions. Meanwhile, he continued his dance studies in earnest.

Responding to an announcement in a Hollywood trade magazine, John auditioned for a summer ballet season at the Greek Theater. Although his dancing skills had been improving, he wasn’t quite sure if they were at a professional level yet. Nevertheless, he was both surprised and delighted at being chosen for his first true professional dance job.

Located in Hollywood’s Los Feliz district near the Griffith Park Observatory, the Greek Theater was an outdoor summer venue like the more famous and much larger Hollywood Bowl. The Greek attracted many famous artists, such as Judy Garland, Harry Belafonte, José Greco, Katherine Dunham, Victor Borge, Fats Domino, and the New York City Ballet Company.

The theater’s general director, James Doolittle, had engaged the internationally famous Cuban ballerina Alicia Alonso to stage and dance the leading role in the full-length ballet Coppelia, with her partner, Andre Eglevsky. Also, Niels Bjørn Larsen, an equally famous dancer-mime from the Royal Danish Ballet Company, would perform the other leading role as a uniquely skilled puppet-master named Dr. Coppelius, who knew the secret of how to bring inanimate dolls to life.

Alicia arrived in mid-July to conduct the auditions. Accompanying her were six dancers she brought from Cuba, who helped form the backbone of a company complemented by local Hollywood area dancers, and John was one of them. During two weeks of rehearsals and one week of performances, John’s eye was attracted to one of the Cuban girls.

Margarita Guzman was petite…barely five feet three inches tall. She displayed an unusual combination of pale, pearly skin, blue eyes, and dark brown hair…definitely not the stereotypical Latin look John was familiar with. And he loved the way Margarita danced. She always gave it her all, with great feeling and élan. He was especially impressed with her effortless jumping skills…a unique asset, especially for female dancers.

But, more than anything else, John was captivated by eyes that seemingly glowed when she danced. At first he thought that this was just a personal observation, but some of the other local dancers expressed similar comments. Unfortunately, Margarita was not bilingual, and John was embarrassed to expose his rather primitive Spanish language skills.

Another relationship inhibitor was that Margarita always seemed to be huddled with the other Cubans, who kept to themselves for the most part. Meanwhile, she seemed oblivious to John’s attempts at attracting her attention. He thought that maybe she just wasn’t interested, so his curious glances were reduced to ogling, which made him feel like an idiot when she caught him. Giggles from the other girls added to his embarrassment.

The most encouragement he received from Margarita came via captivating smiles during early-morning "Buenos días greetings and end-of-day Hasta mañanas."

Meanwhile, the season was a huge success. And, after the final performance, the Cubans returned to Havana. Two weeks later, John received instructions to report to CIA headquarters near Washington, DC.

Playtime was over.

CHAPTER TWO

Reporting for Duty

The omniscient weather prognosticators had forecasted ninety degrees and humid for this muggy mid-August day. For once, they got it right.

After his cross-country flight from Los Angeles, John grabbed a taxi at the Washington, DC, airport. While edging gingerly through the heavy airport traffic onto an exit lane, the driver said, I’m sorry, buddy, but my air conditioner is on the blink. Just leave your window down…OK? John noticed that the driver had already done the same with his own window. Hopefully the breezy cross-ventilation would provide some relief.

A sweltering half hour later, they were in Ballston, a suburb of Arlington, Virginia. Meanwhile, John felt uncomfortably sticky under his pale blue dress shirt. Loosening his tie and unbuttoning his collar during the cab ride had not helped much. Neither did the car’s open windows. He was greatly relieved when the driver finally announced, We’re almost there.

Not even the hint of a breeze stirred the leaves of stately spruce trees that lined North Glebe Street. The cab pulled up to a stop in front of number 1000. A large, darkly weathered brass plaque identified the unassuming five-story edifice as the Broyhill Building.

What’s the tab? John asked as he reluctantly rebuttoned his collar and adjusted his tie.

The taxi driver swung down the meter’s activation flag. That’ll be $5.85, buddy.

Gathering up his plaid gabardine sport jacket and briefcase lying on the seat next to him, John stepped out onto the curb. He withdrew a five-dollar bill and three ones from his wallet. Meanwhile the driver retrieved John’s suitcase from the trunk.

You got business here? The cabbie nodded toward the rather unimposing building that was CIA headquarters, although no suggestion of its purpose was visible.

The driver had not been particularly chatty during their ride, even when John had asked a couple of typical touristy questions about the sights. Meanwhile, John figured that the guy probably had some idea about what went on inside this rather unassuming building and might be wondering if his fare was a government official, or maybe even a spy. But nothing was said.

Ignoring the query, John said, Here, keep the change, handing the cabbie the four bills that he had just folded in half.

Thanks, buddy. Good luck.

A uniformed armed guard stood just inside the door at the top of well-worn marble stairs. After looking at John’s Agency ID, he said, Check-in is over there, indicating an information desk off to the side of the foyer, where another uniform could be seen talking into a phone.

A moment later, the guard hung up and waited to hear what John had to say.

I received this cable, he said, handing him the telegram.

Your ID, please.

After verifying that John’s name was on the roster of new trainees expected that morning, the guard directed him to take the elevator to the third floor.

Turn right and go down the hall to the second door. You’ll see a bunch of other guys inside. Just go in and take a seat. The director will be here soon. You can leave your bag over there for now, pointing to a row of suitcases lined up along the wall nearby.

There were already a dozen or so other young men in the room…mostly in their mid to late twenties. A few were possibly a little older, John figured. He also noted the conspicuous absence of women and minorities. A couple of quiet conversations were in progress, while others fidgeted nervously in their seats. Other than a couple of courteous nods, no one acknowledged John. It was clear that this was a room full of uneasy strangers. A palpable atmosphere of apprehension hung in the air.

A few minutes later, two men entered. One, a nattily dressed older man, made his way to the front of the room. The other suit closed the door and announced, Please take your seats. Then, when everyone was seated, he said, Gentlemen, meet your director.

The older man had thinning gray hair and a white toothbrush mustache that covered his upper lip. John estimated his age to be early to mid-fifties. He wore wire-rimmed eyeglasses, and in his right hand he held an unlit smoker’s pipe that he handled like a stage prop.

Good morning, gentlemen, he said with a disarming smile.

Following scattered good morning responses, the speaker introduced himself. I am DCI Allen Dulles. I work for the president, and you are coming here to work for me. We all serve our fellow Americans. This task carries with it a great responsibility…the security of our nation. Much is expected, and we shall not let our country down.

His words left no doubt about what he expected from the attendees seated in front of him. Director Dulles was known to be an imposing figure in the intelligence community. A lifelong professional, he epitomized discretion when it came to dealing with the press and inquisitive politicians. Although outwardly a jovial guest at dinners and cocktail parties, it was nearly impossible to pry meaningful information out of him. At such affairs, when pressed to answer probing questions about the latest international crisis…as he often was…he would caress his ever-present pipe while formulating cleverly crafted but evasive replies.

Dulles knew that even democratic societies required the clandestine activities of efficient espionage services to counter attempted intrusions by other world powers. He was often heard to say that it was not just enemies that had to be closely scrutinized, but friends as well. Meanwhile, Dulles had mastered the role of intimate confidant to perfection and had become a great asset to President Dwight D. Eisenhower, whose Secretary of State was John Foster Dulles, Allen’s brother. This unique relationship gave the DCI direct access to the president.

I will begin my remarks, said the director, "by reminding you that there is no such thing as an honest spy. This is a basic conundrum that you must all come to grips with as you complete your training and later perform your assigned duties. This is especially important if you are married or plan to marry in the future. Spouses and other family members are NEVER to know what is going on in your workplace…wherever or whatever that may be.

"In fact, openness and honesty in the spy business are oxymorons. Deception is how we operate, and secrecy is essential to maintain that clarity. In fact, transparency would put our country in jeopardy, as well as fellow Agency officers who are out in the field, risking their lives.

Critics complain that espionage is a dishonest activity that keeps the Cold War sizzling. This is naïve pie in the sky. What they fail to realize is that our enemies will stop at nothing to destroy us. Let there be no doubt…we are fighting a committed adversary in a no-holds-barred struggle. I am determined that we shall be the victors, and I need your help. That is why you are all here today.

He then paused for a moment to let that remark assimilate before continuing. "From time to time, the press becomes preoccupied with what it perceives to be incompetence, even dishonesty, within our intelligence community. This is often the result of misreading the facts. But, if the press had access to real information, we would not be doing our jobs. And the truth is that we do everything we can to make sure that they do NOT have all of the facts. The press is simply not trained to deal with them. And so we prefer the press to remain ignorant in this unique situation." (John paid particular attention to the emphasis given.)

Even in government, critics sometimes demand investigations into what they consider to be misrepresentations regarding certain activities we engage in. What they fail to understand is that we are at war. It may or may not be an armed conflict. Nevertheless, we are besieged by enemies and ideologies that are determined to bury us…literally. Do you imagine that the Soviets and their cronies will play the espionage game fairly and share their secrets with us?

With that question, he paused and looked penetratingly at each trainee before continuing. "Therefore, we must be vigilant at all times and relentlessly pursue our mandate, which is to protect our nation and fellow citizens.

"You also hear detractors demanding public accountings of decisions and actions carried out by our agency. However, what these critics fail to realize is that government agencies dealing with national security must, by necessity, operate without being subject to probing scrutiny. Otherwise our actions could be compromised, placing in danger not only our operatives in the field but also our fellow citizens both here at home and abroad.

"What detractors fail to realize is that a knowledgeable adversary is a more dangerous one. Therefore we take measures to ensure that adversaries are kept uninformed and misinformed.

"Let them grope and speculate. That is not our concern. The more misinformation they swallow, the better. In fact, this barrier is a form of protection for the Agency, especially our undercover operatives in the field, whose lives may be at risk.

For this reason, officers in our service are instructed in certain activities that may seem to be contrary to moral principles. These include how to lie, how to cheat, steal, socialize with criminals, and act out myriad deceptions against friend and foe alike. In other words, we do everything possible to intimidate and take advantage of our enemies’ and…yes…even our friends’ weaknesses. Some people may not consider such actions ethical. Nevertheless, they are part and parcel of our tradecraft. Meanwhile, the training you will receive will expose you to these invaluable tools…and…much more.

The ominous tone of those slowly emphasized remarks was followed by a calculated moment of silence as Dulles let his words be assimilated. John felt that he knew exactly what the DCI meant. Then, Dulles continued his remarks.

"An important aspect of your training is learning how to compartmentalize your lives, with your clandestine work in the Agency on the one hand and, shall we say, your normal lives with loved ones and non-Agency friends on the other hand. These are widely divergent relationships that must never intermingle. In fact, they are incompatible for the most part.

You must understand that intelligence agencies such as ours are, by definition, clandestine organizations…meaning that we make decisions and implement actions in secret. Virtually every country throughout the world does the same, including friendly governments that support each other. However, we must ensure that every decision and action we take is based upon the well-being of OUR country and OUR people, above all else.

There was a long silence…then…Well, gentlemen, that is all for now. It has been a pleasure to meet with you this morning. I’ve read your files, and I’m impressed with your qualifications. I trust that I have given you food for thought and a reason to redouble your commitment to our company’s mandate.

Gesturing toward his deputy…Before you leave today, my assistant here will give each of you a packet of information that explains your training program. Look it over before you leave; he’ll answer any questions you might have. Meanwhile, best of luck to you all.

Then, with a wave, the director about-faced and left the room. His commanding presence and powerful message resonated with every trainee and were a topic of lively conversation for several weeks afterward.

CHAPTER THREE

The Farm

The trainees’ home for the next several months was Camp Peary, known as the Farm. The facility was in a remote area near Williamsburg, Virginia. Originally established as a top-secret Navy Seabees training facility in 1942, the facility consisted of over six thousand acres of mostly unimproved wooded land where myriad clandestine training activities took place for the Central Intelligence Agency.

Each trainee was assigned a fictitious first name. These pseudonyms were stenciled on a patch sewn above the left breast pocket of identical uniforms that they all wore. John’s new name was Phil.

The trainees’ first day began with a general orientation by a senior instructor who explained the life of a field officer and the fundamentals of intelligence work.

Espionage is sometimes described as a game, he said, "And those of us who engage in this game deal with challenges that test ingenuity and cleverness. Most games have goals. But those games usually end when objectives are achieved. On the other hand, spies prefer challenges to be ongoing. They pursue objectives, of course, but not necessarily conclusions.

"Our aim, then, is to be in control. However, our real goal is to secure the advantage and maintain that control…not necessarily to uncover the truth. The game of espionage, therefore, is based on one-upmanship. And we work tirelessly to win this game.

As a rule, spies prefer to diagnose situations using information they have gathered themselves, rather than intelligence obtained from other sources…especially if the intel cannot be verified and is, therefore, questionable. The fact is that planting false information is standard procedure for nearly all intelligence services. In addition, intelligence that spies have gathered themselves helps them validate their conclusions and maintain their control over challenging situations they may or will be facing. This allows them to manipulate circumstances as needed. Therefore, spies prefer to operate in a sea of chaos that is planned by them or for them.

Before continuing, the instructor waited for that puzzling statement to sink in. "This enables spies to take advantage of the resulting disorder by seizing the initiative and directing the game through their own strategy and cunning. Therefore, in order to gain a desired advantage, lies must become true. And, to maintain control, manipulating these false truths is essential. But controlling chaos is only possible when such truths remain a secret…even when they are NOT true. The resulting secrecy then gives lies their essential credibility.

"Another important thing to remember…the press is not our friend except when we use it. Manipulating the controlled chaos we engineer is put at risk when the press uncovers our secrets. Since the press’s objective is to expose the game and place blame, its speculations put all the players in jeopardy, including our own team…even when the press’s conclusions are wrong.

However, an even worse scenario is when an adversary discovers the truth. Therefore, a spy’s security can only be maintained when things remain hidden…when only he knows what is true. Meanwhile, a spy must always assume that his adversaries are trying to do the same things he is doing. Therefore, determining who is cleverest is integral to winning the game.

The instructor stood quietly for several seconds, looking around the room at his trainees before continuing.

"We have learned that spies and their agents are often recruited from society’s elite, who are better connected in spheres of influence, where deceit and duplicity are commonplace. We already know that some of you fit that bill. As a rule, elitists feel no qualms when they bend rules and tweak moral issues to gain an advantage. And good spies are artists. Their legend—what we also call cover—depends on being able to convincingly invent and create lives from nothing.

"When spies are in the field, they usually do not have access to advanced electronic technology. Therefore, HUMINT (which is intelligence gathered from people) is essential. In this regard, spies must be good judges of character and also adept at evaluating human behavior. And to stay ahead of the game, they must be able to accurately evaluate things in proper context.

Finally, the irony about a nation’s intelligence service is that its ability to protect its people is based on secrecy and deceit. Which means that openness and honesty are moral issues for civilians…but not for us.

The instructor then admonished the trainees to never reveal real names to any stranger, nor anything about their pre-Agency backgrounds, nor discuss any aspect of their work with non-Agency personnel, especially with spouses and all other family members and friends.

The instructor asked for questions about what had been discussed, but the room remained silent. Everyone appeared to be too dumbfounded to respond.

He then went on to explain that the CIA was made up of three directorates: planning (or clandestine service), intelligence (or analysis), and administration (management and aid to the other directorates).

The instructor continued, Prep for each directorate is different. All of you are here for operations training, which falls under the jurisdiction of clandestine services. But before we get into the nitty-gritty of tradecraft specifics, you’ll begin your training with several weeks of intensive paramilitary instruction designed to test your physical abilities, ramp up your conditioning, and evaluate your will to overcome extremes of physical exhaustion and mental stress. It’s a lot like a military boot camp. But we tweak it a bit differently than they do.

After a moment, he continued, "The next phase of training will then focus on the case officer’s main job, which is to gather information in the field. Your primary source for gathering intel comes from local agents you recruit. We call them assets. They are the ones who have access to the information we want. We’ll teach you how to spot them and assess them. And then we’ll show you ways to recruit and develop them as partners in the game you are playing.

"You will discover that running assets is easiest when they want to help you. Otherwise, it is sometimes necessary to use more nefarious methods based on greed, blackmail, compromise, or flattery…and yes…even sex. Existing circumstances and your own ingenuity will determine the best approach. But YOU are the decider, and YOU must always be in control.

It is best…and easiest…to recruit local assets who are disillusioned with their leaders or employers. However, no matter what, you must always verify their bona fides, meaning their genuineness. There is always the possibility that they might be double agents put in place to trap you, or they may attempt to recruit you. One way to confirm this is to have a potential asset you are recruiting that gives you sensitive intel you have already previously verified on your own. You should do this a couple of times to be sure that you are not being suckered into a lie or being deceived by an undercover adversary.

Then, during a subsequent class, an instructor explained that propaganda was an important two-edged sword that could both undermine and also support political movements.

For example, propaganda can encourage labor unions and mass media to take certain actions. But it can also be used to spread disinformation designed to cause chaos.

Another training session focused on special operations.

No doubt you’ve heard of black ops. They are always designed so they cannot be traced, because they often involve some pretty nasty stuff, he said, drawing an index finger slowly across his throat. The ensuing questions and discussions on this topic clearly unsettled some of the trainees.

"Meanwhile, an agent’s highest priority is to maintain his legend, which is the identity he is known by in the circle of contacts and assets he is running or associating with. If you use brush passes in public places, for example, you can drop an envelope or a small package into an open shopping bag while walking past your contact, or maybe by bumping into him…literally…or by riding an elevator together…or by swapping identical briefcases.

"Here is where you must use your imagination. Remember that assets are not friends. Always treat those relationships with that in mind. The fact is that everyone WANTS to come out on top. But you are the one that MUST do so.

"You can also run an asset by utilizing a cutout, who is an independent third party. This avoids having to make direct contact with your asset, which is always potentially dangerous.

"Dead drops are another way of passing information without being seen with an asset. Tell signals left at previously agreed-upon locations indicate that a drop site contains intel waiting to be retrieved. A typical tell might be a common object left by the side of a road in a certain place or an indicator in a public area, like a chalk mark or a discarded newspaper left on a lunch counter, etc. It could also be as simple as wearing a certain jacket or hat while you are walking along the street or carrying an umbrella in a certain way or of a certain color or size.

"Spoofing is a disinformation technique designed to deceive observers into believing that an operation has gone bad when, in fact, it has just been moved or changed in some way. Another ruse we sometimes use is the cover stop, which is a meaningless action used to confuse surveillance.

To sum up…covert field officers must always check and recheck the accuracy of the intel they are gathering and the bona fides of potential collaborators. However, sometimes it is necessary to act on gut instinct. Regardless…verify everything whenever possible, especially when you chose a new direction or an alternate way of obtaining the intel you are after.

Then, as John was beginning to adjust to the intensity of the physical training regimen and classroom instruction, there was an unexpected interruption.

CHAPTER FOUR

Fort Benning

Wait up, Phil.

John looked around to see who had used his pseudonym. He was leaving the 7:00 a.m. mess hall breakfast and was heading back to the barracks to prepare for the day’s training session. He was looking forward to learning about the false flag method of interrogation that was used to get information from uncooperative prisoners by handing them over to a feared interrogator.

Looking back over his right shoulder, the only person in sight was a short, skinny-as-a-rail guy with ears that protruded from the sides of his head like a Disney cartoon character.

Instructors at the Farm also used fake names, just like the trainees. Except that theirs were last names only. When addressing instructors, the trainees referred to them as Mr. or Ms., and whatever ID name was printed on the patch sewn above their right breast pocket.

The guy now approaching John was dressed in the same generic military fatigues that everyone wore. No rank was displayed; only Mr. Jones was visible on his name patch. John remembered him as the instructor for the locks and picks class a few days earlier.

In a high-pitched voice that matched his comical appearance, Mr. Jones said, Go on outside and get into the Jeep that’s parked in front. Plans for the next few days have been changed for you. I’ll meet you out there as soon as I round up our other man.

Pushing past the screen door, John stepped out onto the front porch. There was only one driverless Jeep nearby. Another trainee from his barracks was already sitting in the front passenger seat. As John climbed into the back, the guy asked, What’s this all about, Phil?

Damned if I know, John answered.

Before they could begin to speculate, Mr. Jones walked out of the mess hall with another trainee in tow. Climbing into the driver’s seat, Mr. Jones fired up the Jeep as the third trainee squeezed into the back next to John. The three puzzled trainees looked at each other with quizzically raised eyebrows, silently shrugging their shoulders.

A few minutes later, the Jeep pulled up in front of their barracks. Mr. Jones then said, Pack some work clothes in your carry bag…enough for three days. You boys are going on a little trip. You won’t need your tuxes and bow ties, he said with a goofy grin that matched his appearance.

Inside the barracks, the three trainees hurriedly packed what they thought they might need in Agency-issued duffel bags. One of them, a twenty-something-year-old with reddish-brown hair and freckled rosy cheeks, asked, What do you think this is all about? Think we flunked out?

John just shrugged, not knowing what to say.

However, the other guy, whose pseudonym was Jesse, responded, Don’t see how, Charley. I don’t know about you guys, but it’s been pretty routine stuff so far…don’t you think?

John had already pegged this short, nerdy guy as a cocky sort with a quirky attitude that turned off some of the other trainees. John couldn’t quite figure out why Jesse had been recruited for ops training, although John did notice that he seemed to be on top of most of what was being dished out.

With a backward glance over his shoulder toward John, who was rummaging in his locker for toiletries, Jesse asked, What do you think, Phil?

Initially John was distracted and did not respond to his pseudonym.

Then Jesse repeated a bit louder, Hey, Phil, what do you think?

John responded somewhat jokingly, I doubt we’re in any trouble. Maybe they’re sending us out to blow up something. Remember we took that bomb-making class the other day?

Jesse responded, I guess we’ll find out soon enough.

Mr. Jones fired up the Jeep when the three trainees exited the barracks with their carry bags. Somewhat agitated, he called out, Let’s get going. We don’t have much time.

A few minutes later, they were seated in someone’s office they had never seen before. There was no name on the door, no nameplate on the desk, no uniform, and no ID badge. Nor did he introduce himself. The fortyish balding man who was now standing in front of them just remained anonymous. Displaying an aura of authority, his pale gray eyes exhibited a dispassionate expression that rendered him hard to read. It occurred to John that this might be the sign of a good agent in the field.

Mr. Jones came directly to the point, No doubt you guys are wondering what this is all about. He spoke slowly while making momentary eye contact with each of the trainees.

At a loss for words, the three novices nodded hesitantly.

Remember how when you were recruited, you were asked about special ops and how you felt about…let’s just say dealing with particularly undesirable or dangerous people?

It was generally understood that special operations often involved so-called black ops, which included assassinations. John distinctly remembered feeling his throat tighten up during his recruitment interview back at Occidental College when he was asked how he felt about such actions. Although somewhat taken aback at the time, his response had been, "I guess I don’t have any particular objection to the idea…in general…if it’s really necessary. But I don’t know how I’d feel if I was actually face-to-face with someone that I had to…you know…take care