CIA Drug Pilot Claims to Have Flown JFK Assassins Into Dallas
Former CIA pilot of four decades Robert “Tosh” Plumlee details in his new memoir Deep Cover, Shallow Graves intimate details of numerous crimes committed by the Central Intelligence Agency, including their role in the assassination of President John F Kennedy.
In a February 1985 episode of the hit NBC television series Miami Vice, Eagles singer Glenn Frey played a swashbuckling CIA pilot, Jimmy Cole, who flies ace detective Sonny Crockett (Don Johnson) and Rafael Tubbs (Philip Michael Thomas) to Colombia to conduct a drug deal.
Crockett and Tubbs had been recruited by the DEA to work undercover as drug smugglers to help bust cartel operatives.[1]
Frey’s character was loosely modeled after Robert “Tosh” Plumlee, a CIA pilot whose exploits over a 40-year career are detailed in a new memoir, Deep Cover, Shallow Graves, with Ralph Pezzullo.
Contrary to the depiction on Miami Vice, Plumlee’s memoir shows that the CIA often worked hand-in-glove with organized crime and was the one at times smuggling drugs into the U.S.
Plumlee claims that, on the morning John F. Kennedy was killed, he flew Johnny Roselli, a CIA-Mafia liaison, and other members of the assassination team into Dallas.
From Juvenile Delinquent to Covert Agent
Plumlee starts his story by noting that he was paid as a CIA pilot for years through cut-out companies like Riddle and Dodge Corporation and Atlantic Richfield, which had secret government contracts, or through fake “shell companies” like Intermountain Aviation and Mountain State Airlines.
That Plumlee and his colleagues did not know the overall mission was by design, since the world that he worked in was “deeply compartmentalized,” with no “HR” or “discernible structure.” Its hallmarks were “illusion, deception and sleight of hand.”[2]
Plumlee was recruited into this clandestine world at age 16, when he became part of an experimental army unit for juvenile delinquents attached to military intelligence at Fort Bliss, Texas, designated as Triple “A” Recon Training Command, Dog & 8 Company (AAA RTC D-8).
A product of a broken home who would routinely skip school, Plumlee’s father worked for Lockheed Aircraft at Dallas Love Field, a top secret military base where the B-17 bomber (known as the Flying Fortress) and P-38 Lightining were built.
As a kid, Plumlee and his friends would stand at the edge of the runways and inch as close to the flight paths as possible without getting hit.[3] After he was caught sneaking into a plane, an Air Force pilot named Pat McDonald agreed to teach him to fly. Plumlee then forged his birth certificate and joined the Texas National Guard.[4]
Plumlee claims that his group was modeled after a World War II demolition unit called the Filthy Thirteen—a hodgepodge of outcasts trained to infiltrate behind enemy lines who became the inspiration for the 1967 Hollywood film The Dirty Dozen starring Ernest Borgnine, Jim Brown and Charles Bronson.[5]
Plumlee says that, in 1957 at age 19, he was recruited to fly to central Cuba for the purpose of supplying ammunition and weapons to Fidel Castro’s rebels, who were fighting against dictator Fulgencio Batista, who was also being supplied by the CIA.[6]
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https://covertactionmagazine.com/2026/06/09/cia-drug-pilot-claims-to-have-flown-jfk-assassins-into-dallas/