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In 1961, two years after Castro took over Cuba, Plumlee went to work running guns to Castro's right-wing opponents. He says he was attached to the CIA's Miami station in a project known as JMWAVE, the agency's codename for anti-Castro operations. "JMWAVE was the first time I knew I was CIA," Plumlee says. He got to be friends with various members of Alpha 66, a group of anti-Castro extremists recruited by the CIA to carry out terrorist attacks inside Cuba. One of those operatives was Frank Sturgis, who later turned up as a Watergate burglar. "Sturgis and I made flights to Cuba together," Plumlee says. "He was a good friend of mine in the Cuba days. We dropped some leaflets over Cuba together and made an air raid over Santa Clara. But when Watergate happened, I hadn't seen him in years."* * *
Plumlee made numerous flights to Cuba in support of Alpha 66 and other agency-backed groups. "My end was mostly supply stuff," he says. "We would take people out and in, make drops, land and remove people. There was a situation where we removed some missile technicians—defectors—out of Cuba before the missile crisis." He says he was asked to retrieve a few freelance counterrevolutionaries, private citizens who'd launched raids on Cuba. And he flew ABC reporter Lisa Howard into Cuba, where she created a back channel between Robert F. Kennedy and Castro after the Cuban missile crisis. "There was an arm [of the CIA] out there trying to talk peace with Castro during the assassination attempts," he says.
As an ostensibly civilian pilot, Plumlee says he was told to fit in with Miami's anti-Castro contingent. "Nobody actually said ‘infiltrate,'" he explains. "But I was undercover, a ‘cut-out' used by various agencies, but most of the time the CIA provided logistical support. I got heavily involved with organized crime in Florida. The next thing you know, one of my good friends was John Martino. Johnny Roselli was a good friend of mine. I flew Roselli in and out of Cuba many times."
Martino was a Cuban mob-tied bookie and casino operator who escaped to Florida after being jailed by Castro. Roselli was a Chicago mobster who became involved with the CIA's anti-Castro campaign and later wrote a book claiming the Cuban-tied mafia murdered President Kennedy. (Other books have claimed Roselli was involved in the alleged plot.) His decomposing corpse was discovered in an oil drum floating off the Florida coast in 1976, shortly after he testified about the assassination to the U.S. Senate Select Committee on Intelligence. He had been stabbed to death and his legs had been sawed off.* * *
Plumlee's story stretches credulity. His Zelig-like appearances during many of the most exotic moments of covert U.S. government activity seem implausible. And there's more. On Nov. 22, 1963—the day of Kennedy's assassination—Plumlee says he was standing in Dealey Plaza—next to Sergio Rojas, a military operative.
But what seems to start as a yarn best served from a barstool quickly gains the look and feel of real history: the CIA had received information "that a couple of Cubans were going to fire a bazooka at Air Force One in West Palm Beach," he says. "This information came from the FBI. They had information that two Cubans had been arrested with a bazooka. There was talk about Austin, Texas—there was supposed to be a hit on Kennedy."
Both the CIA and FBI, Plumlee adds, were desperate to track down anyone, especially Cubans, who might be plotting an assassination attempt during Kennedy's tour of the southern U.S. And so they sent their Cuba team—including Plumlee—to Dallas.
"We were dispatched to Dallas to check for spotters, to see if we could abort any assassination," Plumlee says. Plumlee flew Roselli and several other CIA assets familiar with the Cuban mafia crowd to Redbird Airport. They stayed at a safe house, he says, and were assigned positions along Kennedy's limousine route.
"This was standard, routine stuff," he says. "Nobody really thought too much about it. Our main task was the south parking lot, south of the [grassy] knoll. The object was to look for the best possible location for shooters, and go unnoticed because we were not supposed to be there. We didn't see anything suspicious."
Seeing is one thing; hearing another. Just as Kennedy's limousine passed the Texas Book Depository, Plumlee recalls that he and Rojas heard a shot from behind them.
"I am familiar with gunfire, and I've said it to Congress and anybody who has a concern about this thing," he says. "We both felt there was a shot that came over our left shoulder where we were standing, from either the parking lot or the triple overpass."
Plumlee doesn't think the CIA or FBI had a hand in Kennedy's assassination, but that gunshot convinces him Oswald wasn't acting alone. "There is no doubt there was a team there to kill the president," he says. "And the fact that there was an abort team tells me there was prior knowledge. But there are people on the Internet saying I flew Roselli and a team to Dallas to kill Kennedy. And to go on a limb and say the dirty CIA planned it all? No, there were elements of the FBI and CIA that tried to stop the assassination."