Fidel Castro enters John Kiriakou’s account not as a Cuban subject but as an analogy, offered in 2025 to defend the American decision to deal with al-Julani in Syria. The premise he starts from is a limit rather than a preference: “wouldn’t it be lovely if we could just choose the people that we wanted to lead each country? But that’s just not real life.”[1]
“Compare it to this. We could have cultivated a relationship with Fidel Castro in the 1950s, when he was a rebel leader, and we didn’t. Fidel Castro was a minor league pitcher for the Washington Senators. He liked the United States. We could have cultivated that relationship, but we decided not to, because we had thrown our weight behind Batista.”[2]
The conclusion he draws is that the cost of backing the incumbent is paid over decades, and that the alternative available in 2025 was not an endorsement of anybody’s record but the avoidance of a repeat: “this time it’s different… we don’t have any choice.” He notes that the approach was not an American solo — Emmanuel Macron “has come out and laid out the red carpet and invited Julani to Paris, and then Keir Starmer invited him to London. So we’re not just winging it here. There’s been a policy hatched by the allies that we’re going to get it right this time.”[2][3]
The most-attempted assassination
Castro is also the standing example in Kiriakou’s account of what the CIA did before there was oversight. What the Church Committee era brought to light in 1975 was that “we had tried a half a dozen times to kill Fidel Castro without any presidential authority to do so” — alongside the agency cooperating with the mafia on half a dozen operations, hiring somebody in Africa to kill Patrice Lumumba, and assassinating the president of South Vietnam. The mentality behind all of it, he says, is “to just pretend the law applies to everybody else, but not to you because you’re the good guy.”[4][5]
The methods are part of why he keeps returning to it. Castro, he says, survived decades of assassination attempts, “some that sound like rejected Austin Powers scenes” — poison pills, exploding seashells, exploding cigars, a contaminated skin diving suit.[6] He raised the list in August 2026 as one of the historical escapes worth setting beside the catering truck transfer.[7]
Inside the building, that history defined the border between the two halves of the agency Kiriakou joined. There were scoundrels when he entered, “but most of them existed in the operations part where they tried to assassinate Castro and did assassinate some other folks” — and the analysts “kept hermetically sealed away from those guys.”[8] Castro’s survival also heads his list of the agency’s analytic failures, the Bay of Pigs and “the victory of Castro” being the first entries in a sequence he runs through Vietnam, the Iran–Iraq war and the Iran hostage crisis to argue that predicting future events is not something an army of analysts can do.[9]
The cheques he never cashed
Kiriakou’s argument for closing Guantánamo Bay turns on a detail about Castro. The Cubans do not want the Americans there, and “in all the years that Fidel Castro was in power in Cuba he never cashed the checks that the American government sent for the rent” on the base.[10][11]
If Castro would not take the money, why keep it? Kiriakou gives three reasons, in ascending order of cynicism: because they can, and because it is a thorn in the side of the Cubans — the least important reason; because Congress passed “a very ill-advised law” in the first year or two of the Obama administration prohibiting the transfer of any prisoner from Guantánamo into an American prison, which he calls an act of sheer and blatant cowardice given that the United States already holds some of the most dangerous people in the world in two supermax prisons; and third, because at Guantánamo the prisoners “simply do not have any rights.” The Senate torture report shows that Abu Zubaydah will never be released under any circumstances, and that when he dies there he is to be cremated and his ashes cast into the Caribbean — which could not be done in the American prison system, where he would have the right to counsel, to appeal and to habeas corpus.[12][13][14]
Still fighting a dead man
The last use Kiriakou makes of Castro is as a measure of how long American policy holds a grudge. “We don’t look at US relations with Cuba. We’re still fighting Fidel Castro, and he’s been dead for years now.” The same, he says, goes for the Russian revolution of 1917 — “we never forget as long as it’s useful not to forget”, and when it is useful to forget, the memory goes down the hole.[15][16]