Cuba 2 Dallas: Direct Line from CIA Assets to CIA Foreknowledge of JFK Assassination
What if the CIA’s most sensitive Cuban Missile Crisis operation wasn’t covered up because of what it revealed about Soviet missiles—but because of what that intelligence later revealed about the assassination of President John F. Kennedy? According to evidence assembled over decades, human intelligence (HUMINT) gathered inside Cuba during the 1962 missile crisis may have provided pieces of a larger puzzle that Army cryptographer Eugene B. Dinkin would later assemble in the weeks before JFK’s murder.
Dinkin accurately warned that Kennedy was going to be assassinated, attempted to alert authorities, and was ultimately confined to a mental institution. A letter he sent to Attorney General RFK, was intercepted by the CIA. Robert “Tosh” Plumlee, author of Deep Cover, Shallow Graves, who was involved in the CIA’s Cuba operations during the missile crisis, and bestselling co-author Ralph Pezzullo, who has spent years documenting the details behind those covert missions and their historical significance, are available.
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- CIA operatives gathered HUMINT inside Cuba before key U-2 missions.
- Tosh Plumlee participated in covert operations tied to AMCOBRA.
- Eugene Dinkin warned JFK would be assassinated weeks beforehand.
- A crucial page from Dinkin’s FBI file remains missing.
- New evidence links Cuba intelligence to unanswered JFK questions.
The Congressional Task Force, headed by Rep. Anna Paulina Luna (R-FL), which is currently investigating the JFK assassination, may have a small clean-up crew sanitizing the truth from coming out. Its report is expected to offer little new information. One reason is that the former CIA contract pilot has plenty to add but is not only being ignored but having his character assassinated. Plumlee previously delivered closed-door testimony to U.S. Senators and committees. As a congressional body, Luna’s task force must have access to all of that. Bill Holen, a close adviser to one of those Senators (Gary Hart), hasn’t heard his phone ring either. He was there for all that testimony from Plumlee.
Most Americans believe the Cuban Missile Crisis was won from the sky. U-2 spy planes photographed Soviet missile installations, President Kennedy confronted the Kremlin, and the world stepped back from nuclear annihilation. But declassified records reveal that critical intelligence was also being gathered on the ground by CIA-backed operatives who infiltrated western Cuba and collected human intelligence directly from inside the island.
At the center of that effort was CIA officer Thomas Hewitt and his highly classified AMCOBRA network. Long before one of Major Rudolf Anderson Jr.’s U-2 flights was shot down by a Soviet missile, covert teams were operating inside Cuba, gathering information on missile sites, Soviet personnel, and military activity. Their intelligence helped shape the understanding of what was actually occurring on the ground and contributed to the intelligence picture that drove American decision-making during the crisis.
Tosh Plumlee was there. While not a member of the canoe team that traveled up that San Diego River, he participated in related CIA-supported operations and personally knew Thomas Hewitt. Plumlee was part of a team that landed on Cuba’s northern coast to retrieve Soviet defectors. When they arrived, two of those would-be defectors were already dead on the beach, one with a note pinned to his chest, warning Plumlee’s crew. Tosh’s firsthand knowledge places him inside one of the most secretive intelligence campaigns of the Cold War.
The question is why so much of this remained hidden for decades.
The answer may lie not in October 1962, but in November 1963.
Army cryptologist Eugene B. Dinkin was assigned to the National Security Agency and specialized in identifying patterns hidden within streams of intelligence. By October and early November of 1963, Dinkin had become convinced that President Kennedy was going to be assassinated. He repeatedly attempted to warn authorities, including Attorney General Robert Kennedy. According to multiple accounts, those efforts were intercepted, ignored, or suppressed. Rather than being taken seriously, Dinkin was declared mentally unstable and institutionalized.
What led him to that conclusion?
One possibility is that Dinkin was seeing the broader implications of intelligence gathered during the Cuban Missile Crisis. The HUMINT collected by CIA assets operating inside Cuba revealed far more than missile locations. It exposed networks, relationships, operational structures, and actors whose significance may not have been fully understood at the time. As a cryptologist, Dinkin assembled what he described as “psychological sets” from disparate pieces of information and concluded that Kennedy’s death was being planned.
An FBI document generated in 1964 and later released contains one of the most intriguing clues in the entire story. On page three, the report describes Dinkin’s discoveries. Near the bottom appears the unfinished sentence: “…this same group planned to…” The next page is missing.
What group? Planned to do what? Why is the continuation absent?
Plumlee and Pezzullo can connect the dots between newly declassified Cuban Missile Crisis operations, the CIA’s ground-level intelligence network inside Cuba, the warnings of Eugene Dinkin, and the unanswered questions that continue to surround JFK’s assassination. If intelligence gathered during the missile crisis pointed toward forces that later emerged in Dallas, it would help explain why so much of this story remained buried for more than sixty years—and why some of the most important records are still incomplete today.
Relevant Article(s):
The Cuban Missile Crisis, 1962: The Photographs
How a CIA agent trained agents who found Soviet missiles in Cuba
PFC Eugene Barry Dinkin (1938-2012) – Find a Grave Memorial
Pilot Tells Untold Cuba Missile Crisis Role – Special Guests
OPTIONAL Q&A:
- How did CIA HUMINT gathered inside Cuba differ from what U-2 flights revealed from above?
- What did Thomas Hewitt’s AMCOBRA network discover that remains underappreciated today?
- Why were ground operations inside Cuba kept secret for so many decades?
- What role did Tosh Plumlee play in the broader intelligence effort during the Cuban Missile Crisis?
- How could intelligence gathered during the missile crisis have later surfaced in Eugene Dinkin’s analysis?
- Why were Dinkin’s warnings about JFK’s assassination dismissed rather than investigated?
- What significance should researchers attach to the missing page in the FBI’s 1964 Dinkin document?
- Did the Cuban Missile Crisis uncover networks and relationships that extended beyond Cuba and into the events of November 1963?
ABOUT RALPH PEZZULLO…
Pezzullo is a New York Times bestselling author, and award-winning playwright and screenwriter. He is also the host of the popular podcast “Heroes Behind Headlines,” which is ranked in the top 1% off all podcasts worldwide.
Born in New York City, he grew up in Mexico, Vietnam, Bolivia, Colombia, Guatemala, Uruguay and Nicaragua as the son of a US diplomat. His over 30 books published include New York Times bestsellers Jawbreaker (with former CIA operative Gary Berntsen), Inside SEAL Team Six (with Don Mann), Most Evil, Zero Footprint, Left of Boom and Ghost. His latest books, both released in 2025, are The Great Chinese Art Heist and Stolen Elections: Takedown of Democracies Worldwide.
ABOUT ROBERT “TOSH” PLUMLEE…
Robert “Tosh” Plumlee is a former contract pilot who claims to have participated in covert aviation operations connected to U.S. intelligence agencies beginning in the early 1950s.
According to his account, he flew missions throughout the Caribbean and Latin America involving weapons transfers, intelligence logistics, and clandestine operations targeting Cuba.
Plumlee has provided statements to investigators examining intelligence activities and the Kennedy assassination over several decades.
ABOUT DORY WILEY…
Dory A. Wiley has studied the assassination of President John F. Kennedy for more than 40 years and is one of Dallas’s foremost independent researchers on the subject. He has done extensive work on the claims made by Robert “Tosh” Plumlee and finds them to be largely unassailable. For the past decade he has hosted an annual JFK Assassination Symposium in Dallas, bringing together researchers, historians, and eyewitnesses to examine the evidence and pursue the historical record. He serves on the Board of the Dallas Historical Society, and the University of North Texas Library. Mr. Wiley is President & CEO of Commerce Street Holdings, LLC, and appears frequently on CNBC and Fox Business as a guest contributor on financial topics.
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