Best of Enemies Page 3

  In the early 1950s, the Platt family relocated to Hingham, Massachusetts, where Jack’s father, by now known as a gifted man with a drinking problem, worked for the city of Boston as a consultant on the civil defense staff, making contingency plans for dealing with fallout from a first-strike nuclear attack. Jack went to Phillips Academy in Andover in 1953 and, from there, to Williams College (in Williamstown) on a full scholarship, the alma mater of a number of CIA vets, later including Director Richard Helms. In the ’50s and ’60s, Williams was still an all-male “Little Ivy” school, consistently ranked among the top five colleges in the country. Ninety percent of the students were pledged to a fraternity, a system that was abolished in the late ’60s. The drinking age in Massachusetts was twenty-one, so weekend road trips across the nearby state lines into New York and Vermont, where eighteen was the rule, were a regularity, and Jack was often the wheelman. When beer wasn’t the quest, girls were, with Jack leading “panty raids” on Bennington and Sarah Lawrence colleges.

  Jack in his 1958 Williams College yearbook.

  (Courtesy Carl Vogt)

  Simultaneously, Jack began to inhabit his cowboy persona. He was a student who, according to one friend, “could drink more than any of us.” Classmate David Grossman described the school as having 250 students in each grade, but Jack stood out. He majored in history, with an emphasis on Russian studies, and consistently made the dean’s list. “I didn’t even know him, but I knew of him,” Grossman says. “Jack was known as a hot ticket, a rough rider, and a tough guy. But at the same time, everybody seemed to like him.” Classmate Joe Albright refers to him as “the wild one at school.” Albright remembers one typical “Jack story”: during a pledge-week party, an inebriated Jack Platt drove his motorcycle into his frat house, the infamous Phi Gamma Delta, up the stairs to the second floor, most assuredly to grab another six-pack. Classmates began referring to the boot-wearing San Antonio native as “Cowboy.”

  Phi Gamma Delta’s president and Jack’s lifelong friend Carl Vogt (who later became Williams’s president) remembers Jack as being the anonymous architect behind some of the greatest pranks in Williams’s history, covert ops that presaged his career as the CIA’s master of surveillance avoidance—only Carl and one other friend ever knew who had pulled off the stunts. At the time, students were allowed only three unexcused class absences, and the school maintained the precious “cut list” in a binder kept in a secure room in the Hopkins Hall administration building. According to Carl, Jack obtained the blueprints for the underground steam pipe system that ran between all the campus buildings, and late one night, he managed to squeeze into the pipeline and traverse it into Hopkins Hall, where he made off with the cut list for all one thousand undergrads. Jack then drove the binder to his favorite New York bar, where he burned the pages in the parking lot.

  Then there was the time when the iconic First Congregational Church in the center of town had its seven-story steeple vandalized. A mysterious person (Jack Platt) had climbed up to the large clock on the steeple and removed all the large gold numerals except for the randy 6 and 9. Or the time when a vintage 1925 fire truck in Bennington was pushed down Route 7 from behind by someone’s car (Jack’s) all the way to the Phi Gamma Delta frat house thirteen miles away. The FBI, called in due to the interstate nature of the crime, was not amused. Jack, then a junior, was fined thirty-five dollars by local authorities. It was one of the only bits of mischief in which Jack was identified.

  Although Jack possessed an impish sense of humor, he was so laid-back that he attained the nickname “The Rock.” He was also known as the smartest guy in the class; he took meticulous—and illustrated—notes, which he lent out to his lucky pals. He was generous not only with his notes but also with his compassion: as pledge chairman, he supported Carl’s move to open the pledging to black students.

  While at Williams, Jack studied with Robert G. Waite, a pioneering teacher who had a great influence on Jack and his classmates. Waite, a psycho-historian specializing in Adolf Hitler, caused intense controversy with his The Psychopathic God: Adolf Hitler (1977) because he attempted to suspend his moral judgment whenever possible, even if the topic demanded otherwise. Later in life, Jack applied Waite’s method when working with spies from the hated Red Menace, the USSR. He already knew he would enter the Marines after graduation, having spent two summers in the Platoon Leaders Class (PLC) cadet program, where he consistently ranked number one among his forty-four fellow cadets.

  Jack missed his 1958 Williams graduation ceremony because he got into a serious car accident while chauffeuring three fraternity brothers on a road trip to Saratoga Springs, New York. He was most likely visiting his sister Polly, a student at Skidmore College who regularly arranged dates for his friends. To avoid an oncoming car, Jack swerved and hit a tree on Route 9. Three of the four men were hospitalized, Jack included. The car was totaled.

  In June 1959, Cowboy married Paige Gordon, a cousin of a cousin, whom he met at a party at about the same time he received a commission as a second lieutenant in the United States Marine Corps. “I thought he was okay,” Paige says with characteristic wryness, but she really started liking Cowboy when she saw how others in their circle responded to his impish sense of humor. Today, slender with short dark hair, Paige looks much younger than a woman in her late seventies. She conveys precisely where she stands with either a clear expression or an economy of words that complemented Cowboy’s rowdiness. From a young age, the Platt girls referred to their parents as “Lady and the Tramp.” Paige was raised by her mother and stepfather in Armonk, New York, on a farm that her family eventually sold to IBM to build its headquarters. Her biological father, Arthur Gordon, was an author and ghostwriter for the legendary motivational figure Norman Vincent Peale. Her mother was very kind when she wasn’t drinking, Paige remembers, but died of alcoholism—a fate that would later prove to be pivotal in how Paige managed her life with her husband.

  Jack was assigned to the Marine corps base at Camp Lejeune, North Carolina, as an intelligence officer in 3rd Battalion, Kilo Company. According to Jack’s lifelong friend Major General Matt “Matty” Caulfield, this was an amphibious task force that often conducted exercises in the Mediterranean Sea. Jack’s key responsibility was prepping and commanding a beachhead assault team. His meticulous field reports saw him promoted in early 1962 to recon leader of Alpha Company, 2nd Recon Battalion. “Jack and I hit it off instantly,” says Caulfield. “I never met a man like him before. He was terrific in the field, never got lost. Jack had a great relationship with the troops. They took to him in a way I’ve never seen before.” Once during cold-weather training in Pisgah National Forest in North Carolina, Jack rescued an entire company from a blizzard. A quarter of them got frostbite, but they all survived. Caulfield says Jack should have gotten an award for this rescue.

  At Camp Lejeune in 1961, three years into Jack’s four-year career in the Marines, a flare grenade exploded in his hand, costing Jack his left middle finger to the first knuckle (later, as a spy, he often wore one black glove to hide this obvious identifying characteristic from the enemy, a habit that conjures up images of Peter Sellers’s Dr. Strangelove, a fictional player in the nuclear game). Caulfield adds some color to the incident, explaining that Jack was such a committed instructor he kept his own unused inflammatory devices for improvisational use during training. These “pyros” he felt were necessary to train his students properly. He had ripped them off and kept them in a hidden locker, buried somewhere unknown to anybody else. A flare grenade went off accidentally one day when he was retrieving his stash. Early in their relationship, Jack told Gennady that he got the injury in a showdown with Carlos the Jackal. Gennady didn’t believe him and could tell that Jack didn’t believe it either when it came out of his own mouth.

  In October 1962, one year after Jack’s first child, daughter Leigh, was born, the Cuban missile crisis almost incinerated everything Jack held dear. During the nuclear brinksmanship, Jack was a first lieutenant in a
Marine reconnaissance battalion off the Cuban coast, ready to scream ashore if and when President Kennedy gave the order. His job was to provide the broader US military with the intelligence needed to pulverize the Cuban—or Russian—military into submission five thousand yards from the beach inland. He fully expected he would be engaged in combat in Cuba when the missiles started flying.

  Before he embarked from Camp Lejeune for Cuban waters, young Jack had told Paige that nuclear war was a strong likelihood. He added that, given what he knew about nuclear war, it wasn’t worth worrying about too much because it would be over faster than the human mind could process. The war he would face in Cuba, however, was a different story. That would be a conventional engagement, and those could be long and bloody.

  Caulfield had a different take on what would have happened in a shooting war based on what he later learned. He says Jack’s battalion was excited about the possibility of a firefight on Cuban shores. What they didn’t know was that there were twenty thousand Soviet soldiers and tactical nukes on the island. Jack’s platoon would have been annihilated.

  While they were training for the big Cuban engagement on Vieques Island, Jack defied orders and surreptitiously made off with better weapons than those he had been ordered to take. Jack and Caulfield were recalled to Camp Lejeune for disciplinary action just as everybody else was heading south during the missile crisis. However, once the general was given the full picture, he chewed out the officer who had moronically ordered them to use inferior weapons in the first place. Jack and Caulfield turned around and headed south to Florida just as the crisis receded.

  After the Cuban missile crisis, Jack returned to Camp Lejeune, and to Paige and baby Leigh, to decompress and contemplate his post-Marines career. He soon had a life-changing conversation with his favorite uncle, Dick Platt Jr., also a former Marine, as well as a member of Yale’s Skull and Bones, a secret society known for its links to the American intelligence community. During a Christmas 1962 exchange, Dick mentioned that because of the empathy Jack demonstrated for his Marine trainees, he might not be capable of invoking the extreme discipline needed in the field and therefore would likely not see advancements in a military career. Dick Platt then suggested a relatively new organization, the Central Intelligence Agency, where Jack might thrive, especially with his having lived overseas and his language skills: German and, to lesser degree, Russian. At the time, Jack wasn’t quite sure what the CIA was. Nevertheless, in 1964, Jack applied and was accepted as a case officer recruit at the CIA.

  2

  ALL ROADS LEAD TO WASHINGTON

  Have you ever killed anybody?

  After completing his operational training at the secret “Farm” facility, located near Williamsburg, Virginia, Jack spent two years at the CIA’s new Langley headquarters, a period that proved instrumental to his great successes down the road. This was due in large part to his being assigned to work with the man who taught him the real tricks of the trade, counterintelligence whiz Haviland Smith, who was referred to as “an illusionist” because he consulted magicians in order to learn about deception and misdirection. Smith soon gained Jack’s friendship and, more importantly, his respect. In addition to being an expert in field surveillance detection and deception, Smith had the confidence of the suits in the Agency’s seventh-floor executive suites. “He knew where all the bodies were buried,” Jack recalled.

  A Russian studies graduate of the University of London and former Chief of Station (COS) in Prague, Hav Smith achieved legendary status among US spies for his innovative methods of combating the enemies’ aggressive surveillance, especially behind the Iron Curtain. In Prague, where Smith’s field officers were subject to crushing, lockstep scrutiny, the COS was forced to become inventive in order to carry out the mission. Thus were born techniques such as “moving through the gap,” the “brush pass,” and the “moving car delivery.”

  A field officer learned to create a momentary gap in surveillance by lulling the enemy into complacency with a repeated pattern of mundane errands done day after day at precise times (going for a coffee, getting a haircut, returning the babysitter, etc.). When the opponent relaxed for a few seconds, certain that the CIA officer was just getting his daily newspaper, a gap in surveillance might be created. And only a few seconds were needed in order to progress to the next Smith contrivance, the brush pass, wherein the officer walks past his asset and, without acknowledging him in any way, makes the handoff. A gap could likewise be created between two cars as the first car turned a corner, with brake lights disabled, allowing the driver to make an exchange or a dead drop through a window before the trailing car made the same turn and spotted it.

  These and other breakthroughs were embraced by Cowboy Jack, and he added to them his Marine-inspired toughness, eventually passing the lessons on to the next generation of CIA officers, the rookies who would be inserted behind the Iron Curtain.

  It wasn’t easy, though. Both Hav’s and Jack’s unorthodox new techniques were constantly met with disapproval from the suits above, who were risk averse in the extreme. Between the Agency bureaucracy and Cowboy, a man who had no interest in careerism and only sought to complete a mission, a tension grew, which only increased over the course of his career. Caulfield says, “The big problem Jack had was with phonies.” It didn’t help that Jack broke the Agency’s dress code on a daily basis with his uniform of a Stetson hat, Lucchese “shit-kicker” boots, tattered blue jeans, and L.L.Bean hunting vest. The nickname “Cowboy,” Paige explains, described more than her husband’s attire and “wasn’t meant as a compliment” coming from his CIA compatriots. The feeling was mutual: “Neckties cut off blood flow to the brain,” Cowboy was fond of saying. “That explains the mentality on the seventh floor.” Even without Cowboy Jack’s sartorial choices, his purposeful gait through Langley’s hallways made him stand out. “Jack moved at warp speed,” one colleague recalls. “I think it was an upshot of his years evading surveillance in the field. I always used to ask him, ‘Where the fuck are you racing to?’ He’d just smile as he disappeared down the hall.”

  Jack’s locker-room language, peppered with his favorite four-letter word, the “f-bomb,” only added to the friction. CIA officer Burton Gerber, who would later become Jack’s boss in the SE (Soviet/East Europe) Division, recalls how he and Jack had to have heart-to-hearts about Jack’s foul language: “I tried to encourage him to tone it down, but Jack never seemed to take the input. He wasn’t confrontational; he just was unaware of how he spoke.” Fellow SE officer Jack Lee explains that “Jack alone was given a lot of slack because he was so good.”

  As to just what set Jack apart skill-wise, his oldest daughter, Leigh, describes it this way: “His whole demeanor is that of a person relaxed and without a care in the world. This face of tranquility and mellowness is deceptive. He doesn’t miss a thing.” Fellow officer Brant Bassett says succinctly, “Cowboy embodied the best of what we were—total dedication to the mission, a hard worker who only cared about helping his country. He was the opposite of the careerists he had to answer to. And a genuine iconoclast.” Jack’s confidant John “Mad Dog” Denton of the FBI says, “When things got crazy, Jack got calm.”

  Claiming that one is motivated by patriotism and not career advancement is a familiar refrain, but Jack made his aversion to bureaucratic upward mobility into high art. “You’re either a headquarters asshole or a street guy like me,” Jack told newsman Dan Rather years later. For Jack, it was all about being posted to wherever the threat to the American “fragile experiment” seemed most acute.

  As Leigh wrote, “For my father, [headquarters] was akin to an assignment in ‘hell.’ CIA headquarters was a stuffy, bureaucratic place filled with power struggles, political turmoil, and overall poor judgment.” Jack often described CIA chiefs as having an old OSS “parachute mentality,” meaning that if someone could parachute into Europe during the war, they were considered qualified to work at the CIA. “For the next year, he worked at Langley and kept his eye
s and ears tuned for other assignments.”

  In 1965, relief from the cubicle tedium came in the form of a coveted posting in Vienna, Austria. The Platt family now numbered five, with twin daughters Michelle and Diana born the previous year. “Paige knew what I did,” Jack readily admitted. “It’s up to each overseas case officer whether to tell his wife. In fact, Paige became my reports officer.” Reports officers edited CIA operatives’ memoranda and sent them back to headquarters for review. “She also helped when it came to entertaining. At a party, I’d say, ‘That’s the target. Put on your best bra.’ She gave me a .357 Smith & Wesson Magnum for my thirtieth birthday. I also have a Marlin 336 and a .30-30 Winchester, model 1854. But Gennady was much more proficient with guns than me.”

  Paige describes attending an endless procession of “smile parties” in Austria where everyone drank and the wives just smiled until their faces hurt. Wives often served as their husbands’ eyes and ears. “Everybody drank too much,” Paige says, admitting she was not a good drinker and was mindful of her mother’s all-consuming alcoholism.

  On returning to the US a few years later, the Platts bought a two-story red brick house on Myer Terrace in Rockville, Maryland, but it was to be mostly rented out, as Jack would continue to solicit and accept overseas postings—anything to get away from headquarters. He hoped he wouldn’t be posted to the hot spot, Vietnam, where he wouldn’t be allowed to take his family. That wouldn’t work for Jack—he knew how many Agency families had been fractured by the absence of fathers.