The Devil’s Chessboard (8.8/10)

Ryan Trimble
7 min readAug 15, 2021

The Devil’s Chessboard is a book by David Talbot detailing the life of Allen Dulles, the origin and development of the Central Intelligence Agency, and the assassination of John F. Kennedy.

Talbot begins by depicting the early life of Allen Dulles and continues to use a biographical framework through Dulles’s time in the OSS (Office of Strategic Services) during World War Two. Here, Dulles was stationed in Bern, Switzerland collecting intelligence among a number of influential academics, intelligence officers, military brass, and political figures.

Talbot details Dulles’s participation in Operation Sunrise, an intelligence operation that allowed Nazi SS officers led by (Waffen-SS General Karl Wolff) to escape death at the hands of Italian communists (and later escape prosecution at the Nuremberg Trails.) The OSS prevented Wolff from being captured or killed in Bolzano until a favorable surrender (for the United States and the U.K. could be facilitated. This was done without the approval of president Franklin Roosevelt, who had stated his intent to pursue unconditional surrender after his participation in the Casablanca Conference with British Prime Minister Winston Churchill. Dulles’s calculation was as such: Allowing Wolff and his army to be captured by Italian communists or the Red Army would increase the probability of Soviet influence in Italy after the conclusion of World War Two. Dulles’s attitude is illustrative of the prevailing attitude of American/British intelligence at the time: The Soviet Union, despite their participation with the Allied Forces in World War Two, were just as much, if not more of a global threat than Nazi Germany. This is also evident in U.S. treatment of German General Reinhard Gehlen who was the Chief of the FHO (Fremde Heere Ost or Foreign Armies East,) the Nazi military intelligence organization overseeing the Soviet Union. Realizing that Gehlen and the rest of his intelligence command could be a valuable asset during the impending Cold War, the United States granted Gehlen and his men immunity from possible prosecution for war crimes. Gehlen and the rest of his men would later establish the “Gehlen Organization” a subordinate Soviet intelligence agency to the C.I.A located in West Germany. Throughout his account of World War Two, Talbot also details the global financial connections that large United States businesses had with German banks and manufacturers (including IG Farben, manufacturers of the poison gas Zyklon B that was used in concentration camps.)

The OSS was not meant to be permanent, but with the Cold War impending, many OSS officers felt it necessary to form an official “intelligence” branch of the United States government detached from the military. Dulles was a key agitator for the establishment of the C.I.A, as he felt returning to normal life at institutional Wall Street law firm Sullivan and Cromwell a bit boring. United States president Harry Truman would go on to establish the C.I.A in 1947, with its stated purpose to be centralizing information and presenting it to the president. Obviously, the organization has expanded far passed it’s original purpose, something that Truman would argue in an editorial shortly after the assassination of John F Kennedy in 1963.

From the origin of the C.I.A in 1947 until the fall of the Soviet Union in 1991, the C.I.A would pursue containment and disruption of the global spread of communism at any cost. Particularly after Eisenhower’s election in 1952, the C.I.A would grow exponentially in size and influence. Dulles was appointed Director of the C.I.A in 1953, which presented an interesting arrangement, as his brother John Foster Dulles was appointed Secretary of State.

The first coup catalyzed and financially supported by the C.I.A took place in Iran in 1953. “Operation Ajax” entailed the deposing of democratically elected Prime Minister Mohammad Mosaddegh. Mosaddegh had agitated for nationalization of Iranian oil fields, fields that were being drilled by the British controlled Anglo-Iranian Oil Company. Judging Mosaddegh to be an unreliable leader, the C.I.A facilitated a coup removing him from power to strengthen the rule of the Shah, Mohammad Reza Pahlavi, who was more amenable to Western interests.

This pattern continued in 1954, as Eisenhower authorized operation “PBSuccess,” a coup d’etat of democratically elected Guatemalan president Jacobo Arbenz. After his election in 1951, Arbenz had attempted to nationalize some of the land that was currently being farmed by the hugely influential, American, United Fruit Company. The Dulles brothers had previously represented the United Fruit Company at Sullivan and Cromwell; the company had many ties to influential Defense players. The C.I.A armed militant Carlos Armas and his supporters, in addition to facilitating bombing raids during the 1954 coup attempt. Four decades of Guatemalan Civil War would follow after Armas was instated.

As the United States government continued to pursue a strategy of “containment,” Cuban socialist Fidel Castro overthrew the government of U.S. backed Fulgencio Batista in 1959, only approximately 500 miles off the coast of Florida. Castro would be a longstanding annoyance to the United States Empire, and would withstand many coup/assassination attempts for decades. Many influential mafia figures such as Meyer Lansky lost millions of dollars with Castro’s nationalization of American owned casinos and hotels. Castro would also go on to nationalize American oil refineries and other businesses.

Between major losses on Cuban investments, and the prevailing attitude towards socialism/communism during the Cold War, there were many powerful people who wanted Castro deposed and dead. These groups included mafia members, the C.I.A, the United States military, members of American high finance, and anti-Castro Cubans in South Florida. This resulted in “Operation Mongoose” and “Operation JMWAVE,” C.I.A plots to depose Castro. Despite many failed attempts, Castro remained in power.

John F. Kennedy was elected president in 1960 after defeating Richard Nixon. Despite much anti-communism/anti Soviet Union sentiment in his campaign rhetoric, Kennedy was less of an imperialist than his predecessors. However, Kennedy did give Dulles and the C.I.A permission to proceed with “Operation Zapata,” which would later be known as the failed Bay of Pigs. The United States government funded a group of about 1000 anti-Castro Cubans to put boots on the ground in Cuba and overthrow the Castro government. Talbot and other historians speculate that Dulles knew that the operation had a high probability of failing, but that those high up in the intelligence community had made the calculation that if the operation was on the verge of failure, the United States military would intervene in their favor. However, that did not happen, and Castro and the Cuban army were able to put down the Bay of Pigs invasion.

The failed Bay of Pigs was a major black mark on the early Kennedy presidency, and as a result, Kennedy developed a healthy skepticism towards Dulles and the C.I.A. Additionally, Dulles and the C.I.A had been involved with facilitating a failed French coup against Charles de Gaulle in 1961 (after France granted Algeria its independence), a president that Kennedy supported and had a good relationship with. Additionally, the C.I.A had purportedly been involved with the assassination of democratically elected Prime Minister of the Congo, Patrice Lumumba, without the approval or endorsement of Kennedy. As a result, Dulles was eventually relieved of his duty in November of 1961, after Kennedy had forced him to resign amicably.

Even after the failed Bay of Pigs, the C.I.A still pursued a changing of the guard in Cuba. After Kennedy’s redecoration of the C.I.A, and after it became public that Kennedy had interest in withdrawing from Vietnam, many military members, financiers, political antagonists, and intelligence officers felt that Kennedy was too “soft” on communism, and that his hands off approach constituted a national security threat.

Kennedy was purportedly assassinated in 1963 by solo actor Lee Harvey Oswald, a former low level military office and former defector to the Soviet Union. However, Talbot casts doubt on the theory that Oswald acted individually. Ironically, after Dulles was forced to resign from the C.I.A by Kennedy, he was appointed to the Warren Commission, the United States’ official investigation into the Kennedy assassination.

As previously stated, Talbot provides many details that cast doubt on the Warren Commission’s conclusion that Oswald operated as a solo actor. Primarily, after his return to the United States, Oswald seemed to often be handled by people that had tenuous connections to the C.I.A, such as George de Mohrenschlidt and Ruth Paine. In fact, Ruth Paine got Oswald his job and the Texas School Book Depository, the building that Oswald purportedly shot Kennedy from. Ruth Paine’s father, William Avery Hyde, was a member of the OSS. de Mohrenschlidt was introduced to Oswald through Dallas C.I.A operative J. Walton Moore.

Talbot also casts doubt on the “magic-bullet theory,” the popularly accepted theory that posits that one bullet from Oswald’s rifle caused seven entry/exit wounds through both Kennedy and Texas governor John Connally.

Talbot also contends that Oswald’s assassination, two days after Kennedy’s assassination, by mafia (and Meyer Lansky) connected Jack Ruby is also indicative of the fact that the Warren Commission’s narrative is likely incorrect, and that the truth was obfuscated by Dulles’s inclusion in the Warren Commission. Congress would eventually reinvestigate Kennedy’s assassination in 1979, however, de Morenschlidt committed “suicide” before he was able to testify(by a shotgun wound to the back of the head.)

Talbot also briefly touches on the assassination of Robert Kennedy, five years later, by Sirhan Sirhan. Talbot speculates that Sirhan could have been a participant in operation MKUltra.

Ultimately, Talbot ends the novel by giving an account of career C.I.A chief of counterintelligence James Angleton’s dying words:

“Fundamentally, the founding fathers of U.S. intelligence were liars,” Angleton told Trento in an emotionless voice. “The better you lied and the more you betrayed, the more likely you would be promoted. . . . Outside of their duplicity, the only thing they had in common was a desire for absolute power. I did things that, in looking back on my life, I regret. But I was part of it and loved being in it.”
He invoked the names of the high eminences who had run the CIA in his day — Dulles, Helms, Wisner. These men were “the grand masters,” he said. “If you were in a room with them, you were in a room full of people that you had to believe would deservedly end up in hell.”
Angleton took another slow sip from his steaming cup. “I guess I will see them there soon.”

The book is highly informative and extremely though-provoking. One of my favorite historical reads to this point. 8.8/10.

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Ryan Trimble

Cornell '19 Economics. Financial Analyst. Weight-lifting and sports enthusiast.