
Eat Yer Puddin
On my Cold War podcast, I’ve been talking recently about the infamous Bay of Pigs debacle. This is where the United States, in 1961 under JFK, tried to overthrow Fidel Castro by launching an invasion of Cuba. It went horribly wrong and was crushed by Cuba. It entrenched the animosity between Cuba and the USA, pushed Cuba into the hands of the USSR, lead directly to the Cuban Missile Crisis, created animosity between JFK and the CIA, and between JFK and the Mafia, and might have played a role in his assassination three years later.
A small, poor, under-developed country defeated the great and powerful United States… in a couple of days.
I’ve known, or I’ve thought I’ve known, the basic story for decades, but the more I’ve drilled into it, the more fascinating it has become.
And, of course, it contains warning for investors, which is why I’m bringing it up.
The first thing to understand is that it didn’t start out as an invasion plan. The original idea, which started under Eisenhower, was created pretty quickly after Castro won his revolution against the Batista government (the latest in a long series of corrupt and violent puppet Cuban administrations controlled by the United States). A little over a year after Castro’s December 1958 victory, Eisenhower approved the secret “Plan for Covert Action Against the Castro Regime”.
The plan talked about creating an exile-based opposition, a covert intelligence and action network inside Cuba that worked with the leadership in exile, and a paramilitary force of Cuban exiles trained outside Cuba who would take guerrilla action inside Cuba. It was all supposed to be kept totally secret and under no circumstances should it every be tied back to the government of the United States. All hush hush, a secret overthrow of a foreign government. Like they had pulled off in Iran and Guatemala a few years earlier.
.… then someone started adding things. A combined air and sea assault. A march on Havana. Possibly US troops. By October 1960, what began as a quiet covert infiltration had turned into D‑Day Jr., and nobody seemed to notice the plan had completely gotten away from them.
Jacob Esterline, who was the Bay of Pig Project’s first CIA director, later summed it up like this: “How did this thing start to steamroller and get away from us?”
Before you know it, they are storming the beaches. Of course, Castro knew they were coming — it was the worst kept secret in Latin America — and he had troops waiting for them. JFK, the newly-installed POTUS, allowed it to go ahead, but panicked at the last moment and cut air support, which meant the troops who landed were sitting ducks for the Cuban air force.
In 1996, a group of scholars from Cuba and the United States, former members of Kennedy’s White House, the State Department, the CIA, Department of Defense, came together to read what were then recently declassified documents, and try and reconstruct and understand what happened. The bottom line was — it was a complete clusterfrack.
Nobody “owned” the mission. Everyone assumed someone else was in control. The CIA thought they knew better than the Cubans on the ground. JFK thought someone in the CIA knew what they were doing. After toppling Mossadegh in Iran in 1953 and Arbenz in Guatemala in 1954, CIA veteran Samuel Halpern says the agency concluded you could do regime change “with mirrors.”
How many times do we see this play out in the business world? Some CEO has a big, bold vision. They sound like they know what they are doing. Other people in the company think the CEO must know what she is doing. After all, she’s the CEO, right? Getting paid millions of dollars. Got that nice big office. A rubber plant in the corner and everything. Being interviewed by Alan Kohler. Mergers. Acquisitions. International expansions. Pivoting to AI and data centres and.… something something dark side.
And it fails. Big time. Turns out, things are much harder than they sound.
Your big vision and $6.50 will buy you a cup of coffee.
Which is why in QAV, we pay little attention to big stories and prefer to look at the quality of the execution — the numbers. Are they making money? Do the numbers indicate they seem to have a handle on the business? The proof of the pudding is in the eating.
The stories are all around us. Companies keep turning them out and we keep tuning them out. Today it’s all AI-this, data centre-that… remember in 2021 when it was BNPL? We all know what happened to Afterpay (acquired by Block). But there were others. Zip were worth $4bn in 2021 — today worth about $2.4bn, down roughly 40%. Humm worth A$421m in 2021, today worth about A$246m, down roughly 40%. Openpay worth $120m in 2021, went into receivership in 2023 and then into liquidation. Sezzle is the stand out — it was worth $1.17bn in 2021, left the ASX in 2024, now trades on Nasdaq as SEZL, worth $5.9bn. Winners and losers. The difference is in execution.
It was around 2021 when Alan Kohler told Tony “this time it’s different”, which is why I had a nice laugh when I watched his son Chris’ recent TikTok.
Back to the Bay of Pigs. Here’s my favourite story from a recent episode.
The Deputy Director of the Central Intelligence Agency during this time was General Charles Cabell. JFK forced him to resign after the failed invasion. His brother? Earle Cabell. Guess what job he had in November 1963? He was the 48th mayor of Dallas from 1961 to 1964. In 2017, documents declassified under the JFK Records Act revealed that Cabell had been a CIA asset since 1956.
One version of John F. Kennedy assassination conspiracy theories, the “Renegade CIA Clique” theory, implicates Cabell and his brother. This theory claims that Earle Cabell re-routed Kennedy’s motorcade (which then passed closer to the Book Depository) as a favour to his brother.
Fun fact: Both Cabell brothers were tenth-generation descendants of Pocahontas, the Native American woman who was captured and held for ransom by English colonists in 1613. She was married off to an Englishman, taken to England where she was shown off as an example of the “civilised savage”, and that is where she died aged 20 or 21 “of unknown causes”. She had one child.
So Pocahontas’ great-great-great-great-great-great-great-great-grandsons might have conspired to assassinate an American President.
That’s some long term payback.
And that’s what we like in an investment, too. Long term payback.

QAV Myth Killers is a weekly column in the QAV newsletter, taking apart a piece of
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