Labyrinth of Enigmas: The JFK Assassination

Lee Harvey Oswald

Bob Bates —

When Jack Ruby died in prison on January 3, 1967, barely three years after he ended Lee Harvey Oswald’s life with one fatal shot to his gut, any information Ruby had on a JFK assassination plot went to the grave with him. The Warren Commission, operative between December 1963 and September 1964, had attempted to interview Ruby early on in their information gathering, but he declined to offer any specifics. Ruby stated he did not feel safe talking in Dallas and, on at least eight occasions over the ensuing months, requested to be securely flown to Washington for a lie detector test and testimony under oath in safe conditions. True, Ruby had more than 30 years of connections within organized crime and was far from a model citizen. But the President’s Commission on the Assassination of President Kennedy headed by US Supreme Court Chief Justice Earl Warren, better known as the Warren Commission, never opted for further interrogation. Critics of the Commission say this was because it had already decided its conclusion: that both Oswald and Ruby had acted alone, thus there had been no conspiracy and, now, the nation could breathe a sigh of relief and move on. Indeed, within days of the assassination FBI director J. Edgar Hoover had wrapped up his lightning-fast review of facts, assuring the Commission of no other skullduggery.

But in the mid to late 1960s, after digesting and analyzing the Warren report, critics began openly doubting its veracity. Skepticism gradually spread and independent investigators wrote and spoke of tangled webs of contradictory and self-serving evidentiary conclusions by the composers of the Commission report. Much of the process of the official investigation and some of the procedures used to reach conclusions were widely criticized. It also seemed that some witnesses had been overlooked and some evidence excluded, raising doubts about or contradicting the Commission’s conclusions.

By the 1970s it became unavoidable that further official scrutiny was needed regarding the whole host of Warren Commission deficiencies. Congress finally acted, authorizing no fewer than three bodies to delve deeper into events, involved persons and organizations, and details that had not yet seen full daylight. First, the Rockefeller Commission, over five months in 1975, looked into the role of the CIA and FBI. Then, over 15 months extending well into 1976, this expanded into the Senate Intelligence Committee, which examined wider roles of the intelligence community within broader contexts of the assassination. And finally, between early 1977 and March 1979, came the House Select Committee on Assassinations (HSCA), further extending investigations in hopes of arriving at elusive conclusions.

Frustratingly, all this seemed to further obscure what had gone on behind the veils of domestic and international intrigue. Comprehensively assessing the scene in 1985, assassination historian Henry Hurt concluded:

The seeds of neglected evidence sown across the landscape in the wake of the assassination have matured into a jungle of powerful contradictions. … This entanglement has become so impenetrable that no single theory, no final answer, can break free to stand unchallenged as a solution to modern America’s most momentous crime. There is too much that is not known, too many facts that remain hidden, for a clear answer to emerge. … Too much pertinent evidence is either missing, destroyed, or languishing under seals of national security.

By 2017, documents released as a result of the John F. Kennedy Assassination Records Collection Act of 1992, decades of materials obtained through the Freedom of Information Act, and declassified documents released from the National Archives collectively failed to clearly illuminate how the assassination happened, who was involved, and who knew what and when did they know it.

Oswald: His Formative Years, Military Service, and Defection

Marguerite Pic Oswald gave birth to three sons: John Pic, Jr., Robert Oswald, and Lee. Lee’s father died two months before he was born on October 18, 1939. Half-brother John was then seven, and Robert, five. Mom and the boys had only three years of comfortable living, between 1944 and ’47 during her third marriage to a professional engineer, when they lived in a nice Fort Worth, Texas suburb with good schools. The family was able to vacation and travel during summers. Otherwise, daily life was often a budgetary challenge, marked by numerous relocations.

Lee Harvey Oswald

A probable formative period for Lee occurred in 1952 when John and Robert both enlisted in the military and Marguerite and Lee moved to New York City to be close to Robert’s base (Marguerite had split up with her third husband). When Lee was 13, his public school attendance was spotty, as he preferred to explore the big city, using the vast subway system in search of adventure, or to stay home watching TV or reading. In 1953 he was picked up for truancy while at the Bronx Zoo and placed in the New York City Youth House for a six-week observational period. Lee was assessed as of “bright-normal” mental range with an IQ of 118 and a well-developed vocabulary and abstract thinking capacity. He was observed as being friendly but quiet with a tendency to be withdrawn. His interests were reading books and magazines, and he spoke of a Marxist pamphlet handed out to him on a street corner. His favorite TV show was I Lived Three Lives for the FBI, and he expressed a desire to join the Marine Corps.

Felt to be adequately well-adjusted with a healthy curiosity about the world, Lee was returned to Marguerite’s custody, after which he was elected as president of his eighth grade class. His school attendance was good and his only noted discipline was for refusing to salute the American flag during the morning Pledge of Allegiance.

In early 1954 Marguerite and Lee moved back to New Orleans. During the next year-and-a-half Lee became a voracious book reader, and Karl Marx became his hero. He was socially active on the streets near their French Quarter apartment. Biographers note that at age 16 Lee would regularly turn discussions among peers or adults to the topic of politics and capitalists’ exploitation of the working class, including as an example his mother’s hard times. As a teenager he began subscribing to socialist and communist publications.

It is a puzzle that young Lee saw little contradiction between his emergent sociopolitical views and his desire to join the US Marines. Upon turning 16, he faked papers and tried to enlist, but the Marine Corps recruiter told him to come back in a year. Lee did, signing up at age 17 and shipped out to a basic training ten-week boot camp, eight weeks of combat training, six weeks of general Naval Air Technical Training, and three months of aircraft control advanced technical training in which he ranked seventh in a graduating class of 30. Then, in September 1957 it was off to his assignment as a radar operator with Marine Air Control Squadron One (MACS-1), at Atsugi, Japan, 35 miles southwest of Tokyo.

Atsugi was a large and important military base, with squadrons of fighter jets, radar and submarine-detecting aircraft, a CIA Asian base, and the Top Secret U-2 high altitude reconnaissance plane, uniquely designed to cruise at 90,000 feet and equipped with sophisticated photographic technology.

Marines at Atsugi visually observed takeoffs and landings of U-2s and even took personal camera shots of them. On the job in their “radar bubbles” they tracked U-2 flights across Chinese and Soviet territory knowing these flights were gathering important intelligence from an undetectable altitude. What is not known is what effect such experience and knowledge had on then barely 18-year-old Oswald.

This is the departure point between what is known about Oswald, what may or may not be valid interpretations or accurate subjective conclusions, what can only be speculated upon, and what is part of the murky uncertainties and unknowns surrounding his life from age 19 on. What is known is that Oswald somehow managed to become competent in the rudiments of the Russian language. He notably spent a series of unaccounted leaves alone away from the base. When seen in Tokyo he was routinely in the company of civilians who reputedly were part of slippery activities; and he spoke critically of America’s role in world politics, especially about what he regarded as the oppression of poor people.

Upon completion of his 13-month Atsugi assignment, Oswald studied studied Russian at MACS-9 in Santa Ana, California, and became conversationally fluent, often engaging for hours at a time with other Russian speakers enrolled in or associated with the base language school. He also developed an interest in Cuba, visiting the Los Angeles Cuban consulate and writing to the Washington DC Cuban embassy. And he constructed plans and obtained documents to travel to Scandinavia and Europe.

Within three weeks following his September 1959 discharge from the Marine Corps, approaching his twentieth birthday, Oswald traveled by ship, plane, and train to the American embassy in Moscow with the expressed intent of denouncing his US citizenship and defecting to the Soviet Union. In a letter from Moscow to his brother Robert, he wrote, “Happiness is taking part in a struggle where there is no borderline between one’s personal world and the world in general.” In the next few weeks, he virtually dropped off the human radar screen into obscure fogginess, ostensibly lost to American intelligence agencies—and with any meaningful presence denied by the Soviets—for the next 32 months.

Cuba, Conflicts, Concessions, and Conspiracies

Fidel Castro

At the same time Oswald was preparing for defection to the Soviet Union, the Western Hemisphere was heating up. At its core was Fidel Castro and his rebels, who overthrew Cuban dictator Fulgencio Batista on January 1, 1959. By mid-year, the US government was wary of Soviet overtures to Premier Castro, and by late ’59, when it became evident communism was gaining a foothold just 90 miles off Florida’s shores, the administration of Dwight Eisenhower became very disturbed. Coordinated by strident anti-communist Vice President Richard Nixon in Eisenhower’s absence because of health concerns, the Joint Chiefs of Staff, National Security Council, and Central Intelligence Agency drew up plans for the military invasion of Cuba and overthrow of the Castro government.

John F. Kennedy

A piece of this plan would be inherited by the incoming administration of John F. Kennedy when he took office in 1961: the Bay of Pigs invasion. Just three months into his administration, JFK gave the go-ahead, but balked on approving US air support to cover the Cuban exile invasion force. Without air cover the exile army was overwhelmed by the prepared Cuban military—Castro’s intelligence network had become aware of what was to take place—and suffered a humiliating defeat. Ripples of outrage and anger directed at Kennedy came from multiple sources, some going so far as to portray the president as a traitor to the cause. The Joint Chiefs wanted, but did not get, an overt full assault by US armed forces. The CIA, which had supplied training, equipment, weapons and munitions, and boats to dozens of exile groups, was frustrated. The Cuban exile community centered in Miami was especially irate and emotionally anguished. And organized crime, aka the Mafia or the Mob, which had been forced out of Havana’s casinos by Castro—thereby losing lucrative revenues from gambling, booze, prostitution, drugs, and gun-running— had a high stake in seeing Castro removed.

But Kennedy himself was angered, too, feeling he had unwisely given in to overzealous incompetents. He vowed to get revenge, and a main part of the means of vindication was to put his brother Robert in charge of a behind-the-scenes group in the White House, which would draw up, prepare for, and execute a successful Cuban invasion—or the assassination of Premier Castro as a preliminary to an internal Cuban uprising intended to provided the opportunity to launch a US invasion. For a year, beginning in mid-1961, this plan took shape and simmered, but was then interrupted by what would become known as the Cuban Missile Crisis of October 1962.

For two weeks, JFK and Soviet Premier Nikita Krushchev danced on the edge of nuclear catastrophe before arriving at an agreement to defuse the showdown. But this only increased the anger and desire of JFK critics—if not their determination—to see Kennedy removed from office. They now viewed JFK as accommodating to communism in the Western Hemisphere because of his concession to halt sabotage directed at Cuba, leaving Castro in a stronger position than before. Critics were also unhappy with Kennedy’s interest in nuclear deescalation.

By 1963 there is reason to believe—based on documentation that came to light in the 1970s—that elements of the Mob were plotting options for a presidential hit job. Many Cuban exile groups—who called the Missile Crisis standdown “La Segunda Derrota,” The Second Defeat—were already trained in assassination maneuvers by the CIA and felt they had no future with Kennedy in power. Add into this mix that Castro knew he was an assassination target, having stated in late summer to an Associated Press reporter, “US leaders should think that if they are aiding terrorist plans to eliminate Cuban leaders, they themselves will not be safe. … We are prepared … to answer in kind.” In the fall of 1963, the Secret Service and FBI had gotten wind of assassination plots and were investigating them; JFK’s planned visit to Chicago was called off and a motorcade was cancelled during a Miami appearance. These actions took place within weeks of the Dallas trip that would cost Kennedy his life. Nonetheless, we know from hindsight that, at the very least, there was inexplicable laxness or insufficient arrangements for presidential security deployments that contributed to the events of Dealey Plaza on November 22, 1963. The big question is: What group or groups in collaboration were involved?

Motive, Means, Opportunity, and Tangled Webs

Researcher and journalist Jefferson Morley noted that as recently as three years ago the notion of a “deep state” shaping American politics was largely publicly unacknowledged. Yet, with the 1947 National Security Act authorizing military and secret intelligence organizations as comprising literally a “fourth branch of government,” an operative behind-the-scenes dynamic has been influential for seven decades. The CIA’s existence is common knowledge, but exactly what it does and how it goes about its furtive craft remains shadowy.

As for Oswald, Senator Richard Schweiker, point man for the aforementioned Senate Intelligence Committee, stated: “Oswald was playing out an intelligence role. … All the fingerprints … point to Oswald as being a product of … the intelligence community.” Schweiker said that the basic reason for unclear conclusions about Oswald is that the very aim and purpose of intelligence communities is to obfuscate, conceal, lie about, and otherwise prevent outside discovery of their activities. Numerous CIA directors and officials have been known to routinely lie under oath when called for testimony before government committees. Richard Helms, who served as CIA director from June 1966 to February 1973, openly admitted, when confronted with his deceptions under oath: “I wear it as a badge of honor” in affirming that one’s only oath of “unyielding allegiance is to the Agency.”

Jack Ruby

So, chalk one up for Lee Harvey Oswald not being an unstable, “lone nut” acting independently. How about Jack Ruby, who according to the Warren Commission, was the other acting loner? After two years of compiling information, the HSCA concluded, “Ruby’s entire background and business activities were an integral part of a system of criminal operations,” and he played a “role in a sophisticated syndicate operation that involved … powerful underworld leaders” Carlos Marcello (New Orleans), Sam Giancana (Chicago/Dallas), and Santos Trafficante (Miami/Havana). The HSCA noted an almost certain “likelihood of a plot that called for Ruby to kill Oswald whenever he could get to him. The evidence of Ruby’s repeated efforts to reach Oswald … made it appear to us that Ruby was stalking him, ready to shoot him when the opportunity arose.” In essence, Ruby was a “gofer” for the big hitters in the Mob lineup.

As for Oswald, the four years between November 1959 and November 1963 are incalculably mysterious. As Henry Hurt put it, “Oswald’s life is as baffling as a Rubik’s Cube. No sooner does a side start to take shape than another side becomes disordered.” This confusing historical landscape and twisted topography features a “US intelligence community which has created such relentless obfuscation that any firm resolution of Oswald, much less of the assassination, seems virtually impossible,” and that within such trails of deceit it is most difficult to differentiate known lies from unknown lies, known destruction of records from unknown destruction, and apparent clues from deliberate deceptions.

It is well documented that the CIA ran training bases (in/near Miami, the Florida Keys, New Orleans, and Guatemala) mainly filled with Cuban exile wannabees for retaking their homeland from Castro’s rule. It has also been documented that multiple CIA code-named operations called for assassinations, some recruiting marksman shooters. Since the 1930s the Mob has been well known for carrying out hit jobs to eliminate their victims from interfering with organized crime activities. Evidence reveals that US covert operatives attempted to recruit at least one Mob hitman, Johnny Roselli. It is also known that American right-wing extremist organizations and their financial backers wanted JFK out of the picture.

Another mysterious figure in the morass of mystery is the world-roaming Russian emigre George de Mohrenschildt, who was involved with various international covert organizations and appeared to be, for several months, the initial “handler” of Oswald upon his return from the Soviet Union to Dallas in the summer of 1962. At the time of the October Cuban Missile Crisis, which involved U-2 surveillance flights over Cuba, Oswald in his affiliation with de Mohrenschildt had just gotten a job in the Dallas photo processing shop that did the print information on the U-2 photos of the missile launching pads being constructed in Cuba. From there, in the summer of 1963, Oswald went to New Orleans and worked within a two-to-three square block area containing headquarters of the CIA, FBI, anti-Castro organizations, and right-wing groups. After disappearing from sight for several weeks, Oswald reappeared in Dallas in October and obtained his job at the Texas School Book Depository building in early November, from where he allegedly shot JFK.

Talking About What You Know Can Be Hazardous to Your Health …

David Ferrie—who was deeply involved as a pilot for the Mob and as a logistical pilot for anti-Castro CIA operations in the Gulf of Mexico and Caribbean—is also known to have spent time with Oswald on at least two occasions in the summer of 1963. When New Orleans District Attorney Jim Garrison made national headlines in February 1967 with his media announcement that he knew who was involved in the JFK assassination, and that Ferrie was one of them, attention was attracted to the pilot. Five days after Garrison’s announcement, Ferrie was found dead, naked, on the floor of his living room. Just the night before he had been nervously talking with a reporter.

Starting in 1975, Congress initiated three investigations, opening elements of the JFK assassination to new scrutiny. The Senate Intelligence Committee called Chicago Mob boss Sam Giancana for questioning about reported CIA-Mafia plots. The week before his scheduled testimony, Giancana was killed with a gunshot to the back of his head, his mouth, and five times in a semi-circular pattern around his chin.

In the summer of 1975 Johnny Roselli, who had acted as liaison between the Mob and the CIA in 1962-63, testified (rather vaguely) before the Senate Intelligence Committee about his role. In early 1976 Roselli had told to syndicated columnist Jack Anderson about a Castro plan to retaliate against JFK in 1963. In April 1976 the SIC called Roselli back for closed-door testimony. Three months later Roselli’s mutilated, chopped-up body was found inside a sealed oil drum floating in the waters off Miami.

Right-wing anti-Kennedy millionaire William Pawley—a longtime associate of the CIA from its inception in 1947, and a personal friend of Allen Dulles, who served as CIA director from 1951 to 1961, when he was fired by JFK—was scheduled to be among the first witnesses to appear before the HSCA in early 1977. A week later in his Miami Beach mansion, he put a gun to his head and committed suicide.

Seven weeks later Edward Epstein, while conducting interviews for his book on Oswald, spoke with George de Mohrenschildt at his Palm Beach home for a couple of hours. Epstein, aware that HSCA investigator Gaeton Fonzi was in the area to do official government work exploring potential evidence, immediately called Fonzi to tip him off that de Mohrenschildt was available nearby. Fonzi drove to his home and spoke with his daughter, giving her his HSCA card, as de Mohrenschildt was out. When he returned home his daughter told him Fonzi had been there and would be back the next day. De Mohrenschildt didn’t say anything, but went upstairs, swallowed his shotgun barrel and pulled the trigger. The HSCA card was found in his shirt pocket.

Five weeks later Carlos Prio, former Mob casino manager in Havana, was to be interviewed by investigator Fonzi concerning CIA operations with Cuban exiles and the Miami Mob. Just before this was to take place, Prior committed suicide at his Miami Beach home.

Antonio Veciana, well known coordinator of anti-Castro sabotage maneuvers during 1960-63, worked with a covert CIA deep cover handler calling himself “Maurice Bishop.” In September of 1963 Veciana observed “Bishop” in Dallas speaking with a slim young man who Veciana would later identify as Lee Harvey Oswald. Veciana gave extended interviews to investigator Fonzi during the HSCA investigations in 1979. Six months later while driving home in Miami his truck was struck with four bullets through the door, window, and windshield, one shot ricocheting off his head and putting him in the hospital for a several days.

Were these simply coincidences? Were messages being sent? Were the suicides an “honorable way out?”

Dealey Plaza, Parkland Hospital ER, and Bethesda Naval Hospital

John and Jackie Kennedy

As the presidential motorcade wound through Dallas and made its last slowed turn onto Elm Street in Dealey Plaza—a prime location for an ambush with its close tall buildings, an elevated railway, and a fenced off parking lot up behind a grassy knoll—any security deployment other than Dallas police officers was essentially missing. When multiple gunshots rang out, many parade onlookers scrambled or hit the ground, but others scanned for the source of the shooting. Motorcycle escort police dropped their bikes and looked for shooters, then charged toward where they saw suspicious signs. Most of the officers immediately headed for the grassy knoll area, with its full parking lot behind an obscuring wooden fence. Before the motorcade had arrived at least eight spectators looking for a good vantage point had approached either the elevated railway area or along the fence line. Each later related that they had been halted by men in official-looking suits, flashing ID badges, instructing them to move on away from these areas.

Among the 266 known motorcade spectators, versions of the number of shots and their source varied. Thirty-two identified the Texas Schoolbook Depository Building, 51 said the grassy knoll fence area (including two Secret Service agents from the motorcade and several police officers), and most of the others thought both directions. Many people just below the fence on portions of the grassy knoll described the loud shots behind and just over their heads. Several people pointed out the briefly lingering gun smoke at the fence and the smell of gunpowder in the air. How about those official-looking guys with ID badges? There weren’t any, according to the official Secret Service, FBI, and CIA assignment postings!

When the speeding presidential limousine arrived at Parkland Hospital minutes after the shooting and the dying president was treated with desperate measures by emergency surgery doctors and staff, what they observed and medically recorded turned out to be at variance from the official autopsy findings conducted at Maryland’s Bethesda Naval Hospital more than six hours later. Much of the autopsy evidence, particularly the photographs, JFK’s shirt and suitcoat, wound trajectory dictation and diagrams, skull fragments, and the entire brain of the president soon went missing. Also, fragments from bullets have disappeared, rendering any post-event ballistics testing unavailable.

Current Status of Conclusions Surrounding the JFK Assassination

Despite hundreds of civilian investigations over the decades and research into nooks and crannies relevant to the many aspects surrounding the assassination, yielding a multitude of books and articles bringing to light countless relevant details, no single clear explanation of who was directly or peripherally involved, how specifically the plan was executed, or who covered for the perpetrators has been arrived at. Secret files maintained by multiple departments of the CIA remain elusive, perhaps by now destroyed. CIA personnel alive during the 1960s who were involved in clandestine operations connected to the events have either taken their knowledge to the grave or remain still silent. A few covert operatives and Mob characters have, at points over the decades, offered cryptic statements as to their knowledge of or participation in conspiracies to kill the president; their credibility is speculative and, as yet, uncorroborated. It remains uncertain if there still exist any material intelligence documents which have not yet been released—and if there are, to what extent they will be redacted if made public. The only answers may lie with an octo- or nonogenarian whistleblower…

Note: For readers wishing to do their own research, a good place to start is the comprehensive repository of archived materials at the Mary Ferrell Foundation.


Christopher Andrew, The Sword and the Shield: The Metrokhin Archive and the Secret History of the KGB (1999).

Abraham Bolden, The Echo From Dealey Plaza (2008).

Nina Burleigh, A Very Private Woman: The Life and Unsolved Murder of Presidential Mistress Mary Meyer (1998).

Edward Jay Epstein, Legend: The Secret Life of Lee Harvey Oswald (1978).

Gaeton Fonzi, The Last Investigation (1993).

Henry Hurt, Reasonable Doubt: An Investigation Into the Assassination of John F. Kennedy (1985).

Jefferson Morley, Our Man in Mexico: Winston Scott and the Hidden History of the CIA (2008), and The Ghost: The Secret Life of Spymaster James Jesus’ Angleton (2017).

John Newman, Oswald and the CIA (1995).

Anthony Summers, Not In Your Lifetime: The Definitive Book on the JFK Assassination (1980/updated 1989 and 1998).

Joseph Trento, The Secret History of the CIA (2001).

2 thoughts on “Labyrinth of Enigmas: The JFK Assassination

  1. Between 1991 & ’93 Norman Mailer (& team of assistants) interviewed scores of people who knew or associated with Lee Harvey Oswald from childhood on, in New Orleans, Texas, Japan, and Moscow & Minsk in the Soviet Union. Mailer weaves segments from these interviews into a narrative web connecting family, relatives, friends, Marine Corps personnel, US government officials, KGB agents & officers, and transcripts from testimony before the Warren Commission, yielding an 800-page tome in which he attempts to understand Oswald’s thinking, emotional makeup, personality, character, motivations, & intentions: his 1995 “Oswald’s Tale: An American Mystery.”

    Cognizant that what people say represents only perceived (or chosen/screened/edited) portions of the “real” Oswald, Mailer nonetheless runs these observations & impressions through his own filter to arrive at who he concludes the essence of Oswald is. In this process, covering the 24 years of Oswald’s life, Mailer increasingly psychoanalyzes from a distance. Among Oswald’s surviving papers are personal writings which reveal his political views & conclusions on what form of government must be organized to provide humanity with any chance at a just and egalitarian existence. He arrives at an idealistic form which extracts the best qualities from capitalism, communism, & socialism; this eliminates the injustices & flaws inherent in each (especially unmet needs, poverty, oppression, nationalism, & any imperialistic intentions).

    So how did Lee Harvey Oswald get from idealist budding statesman to participant in assassination? Therein lies the mystery of the tale (book title). Over a half-century later this panoramic puzzle has, paradoxically, both too many pieces and insufficient compatibly-shaped pieces to yield a clear portrait. Mailer speculates, but admittedly realizes he cannot arrive at sure conclusions.


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