Recent hostilities between Israel & Iran were preceded by elaborate spy activity, some of which was made public through videos. But the worst such humiliation was suffered by none other than the US, by a country it didn’t fancy much.
Welcome to Plain Sight by Wyzr, where we bring hidden patterns into plain sight. Every week, we explore stories and ideas that help us understand why we are the way we are.
When the CIA got played
There are few who aren’t fascinated by a good spy story. Movie industries across the world have fed on them since the dawn of motion pictures. Countless books owe their success to deftly written spy plots. OTTs are now catching up fast, unsurprisingly.
It’s fair to say that spies are to stories what the violin is to music — hard to master, but in the right hands, creates lasting impact.
In some form or the other, all these spy stories are inspired by real events. Some, like Munich, intend to come close to reality, while others, like the Bourne series, have a greater element of impossibility to them. Even though they’re fantastical, they’re still an exaggeration of what real spies do.
Sometimes, though, the truth is stranger than fiction. We saw a glimpse of it in the recent Iran-Israel hostility.
Just hours after they launched a vicious attack on Iran’s nuclear facilities and defense infrastructure, Israel released videos showing Mossad operatives assembling missiles and explosive drones inside Iran. Reportedly, they had smuggled in truck-mounted launch systems and drone components months earlier, and established a covert “drone base” near Tehran.
The attacks were carried out on June 13, 2025, and killed dozens of Iranian generals. Israel then made the footage public to rub salt in Iran’s wounds. Their message was clear: they won’t just eradicate them, but will also embarrass them in front of the whole world. Expose their incompetence and sow fear among the military as well as the civilians.
The most vociferous cheerleader of this attack was none other than the U.S. They had advance knowledge of Israel’s plans and had provided critical intelligence support. They followed it up with their own assault on three Iranian nuclear sites on June 22 in an act of “self-defense”.
Just months before this, Israel had conducted another audacious covert operation. On 17 and 18 September 2024, thousands of pagers and walkie-talkies acquired by Hezbollah detonated simultaneously, in two separate coordinated events. 42 were killed, including the key members of Hezbollah leadership, and over 3500 injured.
To commemorate this assault, Netanyahu gifted Trump a “golden pager”, modeled after the pager variant used in the operation. Trump also responded positively, calling the operation “grand” and significant.
In fact, he also referred to Netanyahu’s upcoming visit (July) to Washington being a “quick celebration of victory” in the June attacks.
While the superiority of Israel-US was never in doubt, what’s different from previous eras is the open admission of spy warfare and public revelations of the work done on the inside. It’s a complete departure from the initial decades of Mossad, where even the family members of their operatives were unaware of its existence.
And while today the U.S. revels in the success of this (not so) secret agency, they’d never want you to know one particularly embarrassing episode from modern history, which they suffered during the Cold War. And it didn’t come at the hands of the Soviet Union. The perpetrator, in fact, was their tiny but feisty tropical neighbour — Cuba.
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In the early 1960s, the United States was obsessed with bringing down Fidel Castro. After the Cuban Revolution of 1959, in which Castro overthrew the US-backed Batista regime, Cuba quickly aligned itself with the Soviet Union, becoming a Cold War frontline.
The CIA, determined to reassert dominance in Latin America, launched a series of covert operations against the Castro regime. These included sabotage missions, assassination plots, economic destabilization, and the infamous Bay of Pigs invasion in 1961, when about 1,500 CIA-trained Cuban exiles landed at the Bay of Pigs in Cuba, aiming to spark a popular uprising, only to be overwhelmed by Castro’s forces.
Central to all of these plans was the CIA’s belief that it had built a reliable network of Cuban agents on the ground — locals who were supposedly working against Castro and passing valuable intelligence back to the CIA.
What they didn’t know was that almost every single one of its agents in Cuba had been turned by Castro’s intelligence agency — the DGI (Dirección General de Inteligencia). This counterintelligence masterstroke began shortly after the revolution, when Castro recognized that the US would attempt to infiltrate his government. Anticipating this, the DGI, with support from the KGB (Soviet’s intelligence wing), built an elaborate counterintelligence framework.
Whenever the CIA tried to recruit a Cuban citizen — often disaffected soldiers, dock workers, or mid-level bureaucrats — the DGI would intervene, turning them into double agents. These “agents” then fed the CIA a steady stream of carefully crafted disinformation, painting a picture of growing dissent within Cuba, a weakening regime, and a ripe opportunity for regime change. The Bay of Pigs invasion was based, in part, on this faulty intelligence. One reason for its catastrophic failure was that Castro already knew what was coming and from where.
But this wasn’t an isolated incident of Cubans outsmarting the mighty Americans. Astonishingly, it went on for over two decades, well into the ‘80s!
And the clueless U.S. got played all along. They thought they had eyes and ears across Cuba. But Cuba not only knew what the U.S. knew, it also knew what the U.S. believed, and manipulated those beliefs to maintain its strategic advantage.
It wasn’t until 1987 that the U.S. learned about this decades-long prank they had been subjected to. A high-ranking Cuban spy named Florentino Aspillaga, disillusioned by Castro’s arrogance and narcissism, had decided it was enough. From Bratislava, then in Czechoslovakia, where he was last stationed, he drove to Vienna and walked into the U.S. Embassy, expressing his intent to defect.
Over the next few days, he made startling revelations to a former CIA agent. He rattled off name after name of supposedly American spies in Cuba, and declared, “He’s a double. He works for us.”
And not just names, he also described them with distinct details: “That guy you recruited on the ship in Antwerp. The little fat guy with the moustache? He’s a double. That other guy, with a limp, who works in the defense ministry? He’s a double.”
It turned out that virtually every single one of the U.S. secret agents was working for Havana, feeding them information they wanted to feed, keeping it believable enough for the U.S. to never doubt them. And this had been happening since the beginning of the ‘60s!
When it came to light that Aspillaga had defected to the U.S., Castro decided to do what’s now commonplace — rub salt on the wound. He assembled the entire cast of pretend CIA agents and paraded them across Cuba as a mark of celebration. But what happened next was scarcely believable for its time, and spectacularly embarrassing for the U.S.
Castro released on Cuban television an eleven-part documentary series entitled La Guerra de la CIA contra Cuba — The CIA’s War against Cuba. It turned out that the DGI hadn’t just turned agents, they had also recorded the entire process. Meetings between CIA handlers and their “agents” were filmed, surveillance footage was archived, and audio recordings were compiled. The videos were surprisingly high quality, and the audio was crystal clear.
CIA officers supposedly under deep cover has been tracked and recorded nonstop. Their meeting points, code language, places they hid their files and gadgets — all of it was revealed in the documentary. Castro himself is said to have enjoyed watching these recordings, amused by how completely the Americans had been fooled. You can consider this a much more elaborate, pro-max version of the footage released by Israel. Only that the joke was on the U.S. The Cuban government later created internal training materials showcasing how they had deceived the most powerful intelligence agency in the world.
This information remained relatively obscure to the world, owing to its humiliating nature and the U.S.’s dominance in the global narrative. Despite its scale and sophistication, you won’t find the video anywhere on the internet (at least I couldn’t). But if it happened in today’s digitally connected world, it would be nearly impossible to keep this hidden.
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The lack of technology allowed the U.S. to minimize damage to its reputation, to the extent that few today know about the embarrassment they suffered. But countries (and individuals) aren’t that lucky anymore. What would normally be relegated to the background is now easily brought to the fore as a strategic tool. Warring countries are doing it to justify their actions and prove their statements. And individuals are sharing personal accounts of mistreatment at the hands of employers, local language enforcers, cab drivers, or traffic miscreants. If nothing, they at least bring shame to the culprit.
The result of this easy shareability of actions should ideally be a greater aversion to doing something people know is morally and legally wrong. At an individual level, earlier, the more powerful could walk away freely and nonchalantly after committing a crime. Today, doing that is slightly trickier, even if it’s not a complete deterrent. They can still game the judicial system, but the damage to their reputation remains.
Although the implications are similar for countries, it doesn’t seem to affect their decisions or actions. The powerful ones, we know, do what they want to. Unlike individuals, they have other strategic and economic tools that ensure reputation doesn’t weigh too heavily. You can simply slap tariffs if someone acts out of line. Which also leads me to think — even if Cuba had made those videos globally popular, would it lead to anything more than a temporary embarrassment?
Here’s a question for you:
In an age where even secrets get streamed, is reputation still a weapon, or just a PR problem? What do you think?
Simply reply to this email (or write to plainsight@wyzr.in) with your thoughts, and we’ll feature some of the answers in our next edition, next Monday.
What we’re reading at Wyzr
Prisoners of Geography. This book single-handedly elevated my understanding of global geopolitics and how closely connected countries’ geographies are to their current economic and strategic realities. I’ve read it once before, revisiting it now.
Until next time,
Best,
Yashraj
