Welcome back to the Deep Dive. Today, we are
cracking open a file that, if I didn't know better,
I would swear was a rejected manuscript for a
spy thriller. Right. It feels too perfect, too
constructed, but I assure you, every single bit
of this is pulled straight from the historical
record. We are looking at a man who was, quite
literally, a paradox in a pinstripe suit. It
really is one of the ultimate paradoxes of the
20th century. We are looking at a man who projected
this incredibly curated image of the consummate
gentleman. You have the pipe smoke swirling around
him, the Princeton education, the tweed jackets,
the very calm lawyerly demeanor. He had a pedigree
that just screams establishment. Exactly. You
look at his photo and you think, OK, this guy
probably spends his weekends debating tax law
or playing bridge. But this same gentleman, this
tweed wearing lawyer, was the architect of some.
of the most chaotic, controversial, and shadowy
operations in American history. And we're not
exaggerating here. No. We are talking about overthrowing
governments, secret mind control programs, failed
invasions, and spy networks that span the entire
globe. We are talking about Alan Welsh Dole.
The first civilian director of Central Intelligence,
or DCI, the longest serving head of the CIA.
And you could argue the man who defined what
American intelligence looks like in the modern
era. We have a massive stack of source material
to get through today. We've got biographical
records, these incredibly dense official histories
of the OSS and the CIA and government reports
regarding his tenure. A lot to unpack. A ton.
Our mission today is pretty clear. We want to
understand how this one man shaped the machinery
of secrets. We want to trace that transition
from the cowboy spy games of World War II to
the cold, hard, covert actions of the Cold War.
And to do that, we have to look at the specific
operations that defined his legacy. We're going
to touch on the coups in Iran and Guatemala,
the disaster at the Bay of Pigs, and his incredibly
complex and frankly surprising role in the aftermath
of the JFK assassination. It is a wild ride.
So let's unpack this. Where do we even start
with a guy like Alan Dulles? I feel like you
have to look at where he came from to understand
where he ended up. You absolutely do. You don't
just wake up one day and decide to run the CIA.
You really can't understand Alan Dulles without
understanding the Dulles dynasty. he wasn't just
born into a regular family he was born into the
machinery of statecraft born in watertown new
york in 1893 but if you look at the family tree
it reads like a who's who Of the State Department.
It really does. I was looking at the lineage
in the notes here. His grandfather was John W.
Foster. Right, who was Secretary of State under
Benjamin Harrison. A huge figure. And then his
uncle by marriage was Robert Lansing. Secretary
of State under Woodrow Wilson. And then, of course,
the most famous connection, his own brother,
John Foster Dulles. Who was five years older
than Allen and eventually became Dwight D. Eisenhower's
Secretary of State. So just pause and think about
that dynamic for a second. I mean, the pressure.
You have a grandfather, an uncle, and a brother
who all held the highest diplomatic office in
the land. The conversations around the dinner
table must have been intense. Right. You can't
just come home with a B -minus in math. It must
have been. So what are your thoughts on German
naval expansion? It creates a specific worldview.
It's not just patriotism. It's a sense of ownership.
You grow up believing that your family is the
government. You aren't just a citizen. You are
a steward of the state. That's a great way to
put it. Steward of the state. But there's another
layer to his upbringing that the sources highlight,
which is the religious aspect. His father, Alan
Macy Dulles, was a Presbyterian minister. The
sources describe his parenting style as mixing
theological liberalism with stern orthopraxy.
Stern orthopraxy. I had to double check that
term when I was reading through this. It essentially
means correct conduct or strict adherence to
religious practice, right? Exactly. It means
that while the ideas discussed might be liberal
or open -minded, the behavior must be rigid.
He grew up in a parsonage, church daily, strict
moral codes. So it's okay to debate the nature
of God. But you better be home for dinner at
6 sharp. Precisely. And here is a fascinating
detail. His parents didn't trust public education.
They thought it was beneath them or perhaps corrupting.
So Alan was homeschooled by various private tutors.
That is a huge detail. It is. It created this
very insulated, very intense intellectual environment
where you are told you are special, chosen, and
destined for leadership. You don't have the rough
and tumble of the playground to humble you. No,
you're in a bubble, a very powerful, very well
-connected bubble. You are the center of the
universe. So he eventually goes to Princeton,
graduates, teaches in India for a bit. which
is a whole other story we don't have time for,
and then enters the diplomatic service in 1916.
And this brings us to one of my absolute favorite
anecdotes from the source material. It captures
the essence of Alan Dulles so perfectly. Ah,
yes. It's what I call the misconnection of the
century. This is a legendary story in intelligence
circles. It's almost too good to be true, but
Dulles himself confirmed it. He told it on himself.
So set the scene for us. It's April 8, 1917.
Dulles is stationed in Bern, Switzerland, at
the U .S. Embassy. He's a young diplomat, barely
in his mid -20s. And you have to remember, Switzerland
in 1917 is the epicenter of European intrigue.
It's a neutral zone in the middle of World War
I. So it's a hotbed of revolutionaries, spies,
exiles, artists. Everyone who's anyone or wants
to be is there because it's the only place they
can be. Right. So he's the officer on duty and
he gets this phone call. It's a Russian exile
who is desperate to meet with someone from the
American embassy. The man on the phone says it
is urgent. He needs to talk to someone now. A
very insistent Russian gentleman. And dullest.
Well, dullest basically blows him off. He had
other plans. The sources imply he likely had
a tennis date with a young woman or wanted to
socialize at the club. A very Alan Dulles thing
to do. Very. He was a young bachelor in a European
capital. He didn't want to be bothered by some
ranting radical on the phone on a Sunday. He
basically told the guy, look, the office is closed.
Call back tomorrow. So he hangs up, goes to his
tennis match. But the very next day, that Russian
exile gets on a sealed German train to travel
to St. Petersburg to start a revolution. That
man on the phone was Vladimir Lenin. Just let
that sink in. It's unbelievable. The day before
Lenin leaves to ignite the Russian revolution,
an event that would define the next 70 years
of geopolitics and create the very enemy. Dulles
would spend his life fighting alone. Allen Dulles
had a chance to sit down with him and he took
a pass to play tennis. The irony is just staggering.
Dulles himself told this story later in life,
almost as a warning about the perils of underestimating
people. It shows a bit of that aristocratic blind
spot we talked about, doesn't it? The idea that
important things happen to people like us, not
to ranting exiles on the phone. It was a lesson
he claimed he learned. But as we'll see, that
arrogance didn't exactly disappear. Well, his
early career wasn't all missed phone calls. He
actually did some serious work. In 1921, he's
in Istanbul, and he gets involved in exposing
the protocols of the elders of Zion. This is
a significant moment that shows his capacity
for real analysis. The Protocols was this virulently
anti -Semitic text purporting to be a Jewish
plan for global domination. It was fueling hatred
across Europe and even in the U .S. Henry Ford
was printing it, wasn't he? He was. It was a
huge deal. And Dulles, as a young diplomat, dug
into it and helped expose it as a complete forgery,
a Russian fabrication. He even tried to get the
State Department to publicly denounce it. So
on one hand, you have this moral clarity. He
sees a dangerous lie and he wants to expose it.
But then we get into the 1930s and things get
a little murkier. A lot murkier. He leaves the
diplomatic service and joins the law firm Sullivan
and Cromwell, where his brother is a partner.
And he starts meeting with some very questionable
characters. This is where the gentleman lawyer
meets the realities of 1930s geopolitics. Sullivan
and Cromwell was and is a powerhouse. They represented
massive corporate interests, huge German companies.
Dulles served as a legal advisor to delegations
at the League of Nations. He's moving in very
high circles. The highest. He's rubbing shoulders
with Mussolini, with Soviet Foreign Minister
Litvinov. And inevitably, he crosses paths with
the Nazi leadership. The sources say he met Hitler
in 1933. It's astonishing to think about. He
was in the room with him. He was. He met Hitler
in Berlin on State Department duty right as the
Nazis were consolidating power. And what's chilling
is his reaction at the time. He wrote a letter
to his brother, Foster, reassuring him that conditions
under Hitler's regime were not quite as bad as
alarmists were saying. Yikes. Not quite as bad.
That is a heavy statement in hindsight. It gets
worse. He also met Joseph Goebbels, the Nazi
propaganda minister. And Dulles reported being
impressed by Goebbels' sincerity and frankness.
Sincerity and frankness. From the master of lies.
That's a massive misread. How does a guy who
exposed the protocols of Zion fall for Goebbels?
I think it's that club mentality again. Goebbels
was educated. He spoke well. He wore a suit.
Dulles likely projected his own class expectations
onto him. He thought, well, he's a civilized
man. surely he can be reasoned with. It's a very
dangerous assumption. It's a reminder that even
highly educated, sophisticated observers could
be charmed or deceived by the facade of that
regime early on. However, to give Dulles credit
where it's due, he didn't stay in that mindset.
Right. The pivot happens around 1935. Something
changes for him. Yes. He returns from a business
trip to Germany. And by this point, the reality
of the Nazi treatment of Jews has become undeniable
to him. The brutality is out in the open. He
comes back to Sullivan and Cromwell. Remember,
this is a firm making a lot of money off German
business ties, and he leads a movement inside
the firm to close their Berlin office. His brother,
John Foster, wasn't happy about that. Not at
all. His brother objected. Foster was very much
business is business. He thought they could ride
it out, that it was a temporary political situation.
But Allen pushed it through. He forced the issue.
The firm ceased business in Nazi Germany. So
he put his morals ahead of the bottom line. He
did. He even helped some German Jews like the
banker Paul Kemper escape to the United States.
So he went from impressed by Goebbels to actively
closing down business ties and helping refugees
within a couple of years. It shows that he was
capable of changing his mind when the evidence
changed. He wasn't an ideologue in the sense
that he ignored reality. No, he was a pragmatist,
a ruthless one, but a pragmatist. And that pragmatism
brings us to the main event, World War II. This
is where Alan Dulles really becomes Alan Dulles.
The transformation from lawyer to spymaster.
In 1941, William J. Donovan, Wild Bill Donovan,
is tasked by FDR to set up the Office of Strategic
Services, the OSS. This is the precursor to the
CIA. America's first real intelligence agency.
And Donovan needs people who are smart, connected,
and willing to operate in the gray areas. He
recruits Dulles in October 1941. And where do
they send him? Back to the scene of the crime.
Back to Spyland. November 1942. He slips into
Bern just before the borders close completely
as the Nazis occupy Vichy, France. He rents an
apartment at Haringas 23. And for the rest of
the war, this apartment is the nerve center of
American intelligence in the heart of Europe.
I love the visual of this. He's living in this
apartment, completely surrounded by Axis territory,
running a spy ring. It's straight out of a noir
film. And he's not exactly hiding. He's hosting
dinner parties. He's using his social status
as cover. He was building what he called a spider
web of contacts. He was meeting with German emigres,
resistance figures, disaffected anti -Nazi officers.
He had a German assistant, right? Gerovon something?
Gerovon Schulze -Gabernetz. He was instrumental.
But his biggest coup, the source that really
made his reputation, was a man named Fritz Kolbe.
The source is, quote, Dulles calling Kolbe the
best spy of the war. That's high praise. Who
was he? Colby was a mid -level German diplomat
who absolutely hated the Nazis. He was a patriot,
but he saw Hitler as the destruction of Germany.
He traveled between Berlin and Bern carrying
diplomatic pouches. Oh, he had access. The best
access. He would literally strap secret documents
to his legs under his trousers, walk into Dully's
apartment, and unload active German cables. He
supplied Dull with plans for the Messerschmitt
Me 262 jet fighter. The jet fighter? That's game
-changing intel. Absolutely. If the Germans had
gotten that jet into the air sooner, in larger
numbers, it would have devastated Allied bombers.
Dulles getting those plans helped the Allies
bomb the production facilities. Colby also gave
up the identities of numerous German spies abroad.
He was a goldmine. And it wasn't just him. Dulles
also had connections to the Austrian resistance,
specifically... The Meyer Group. Yes, another
critical network. This group provided intelligence
on V1 and V2 rockets, the secret weapons program.
They reported on tank and aircraft factories.
This info directly fed into allied bombing campaigns
like Operation Crossbow and Operation Hydra,
which were designed to take out those facilities.
So he is having a tangible impact on the battlefield.
The intel he's gathering is saving lives and
shortening the war. The sources also mentioned
that this group reported to Dulles about the
mass murder in Auschwitz. Yes, as early as that,
credible reports were coming in through these
networks. It shows just how deep his reach was.
He knew what was happening in the camps long
before it was public knowledge. But being Alan
Dulles, his style of spycraft wasn't appreciated
by everyone. He had a pretty rocky relationship
with the British intelligence service, MI6. Oh,
the British did not like him. No, they did not.
They found him. Amateurs. Reckless. Suspicion
is putting it mildly. They thought he was a cowboy.
The assistant chief of MI6, a man named Claude
Danzy, famously called Dulles a fool. Ouch! A
fool? Why? What was the issue? Danzy said Dulles
swallows false information easily. They felt
he was too eager to make a splash, too trusting
of any shady character who walked through his
door with a supposed secret. They saw him as
undisciplined. And there was a specific case
that really highlighted this, right? The Decevious
case. Right. Hans Berndt Concevious. This is
a crazy story about risk tolerance. Decevious
was a German military intelligence officer, an
Abwehr officer who claimed to be anti -Nazi.
He was one of Adal's key sources. But MI6 didn't
trust him. Not for a second. They were convinced
he was a double agent, feeding Dulles a mix of
real and false information to mislead the allies.
At one point, Eusebius told Dulles that the Germans
had broken Dulles' codes, that they could read
his encrypted messages to Washington. OK, so
logically, you stop using the codes, right? That's
spying 101. If your channel is compromised, you
shut it down. A normal intelligence officer stops
Dulles. He kept using the codes. He sent a report
to Washington about the meeting with DeSevius
using the very ciphers he had just been told
were compromised. That's insane. MI6 was furious.
They thought he was endangering not just his
sources, but theirs too. It was unbelievably
reckless. Why would he do that? Was it just arrogance?
Did he think he knew better than everyone? I
think it was a mix of arrogance and a calculated
gamble. He might have thought De Savias was lying
about the codes to test him, or he might have
thought the intel he was sending was so important
that it was worth the risk. It shows that Dulles
had a very, very high tolerance for risk, a trait
that would define his later years at the CIA.
He believed his intuition was better than the
rules. Always. And that risk -taking behavior
culminated at the end of the war with something
called Operation Sunrise. This is a controversial
one. Very. So it's early 1945. The war is winding
down. Dulles enters into secret negotiations
for the surrender of all German forces in northern
Italy. The goal being to end the fighting there
quickly, save lives. Sounds noble on the surface.
On the surface, yes. But to do it, he negotiated
directly with SS General Karl Wolf. An SS general,
not a regular Wehrmacht army officer, but the
SS. The worst of the worst. A man directly implicated
in the Holocaust. Exactly. And historians have
criticized this heavily. They argue that Dulles
offered Wolf protection from prosecution at the
Nuremberg trials in exchange for the surrender.
Basically, he cut a deal with a major war criminal
to get a strategic win. And on top of that, these
secret talks created a huge diplomatic rift with
the Soviet Union, right? A massive one. The Soviets
were our allies at this point, still fighting
and dying on the Eastern Front. Stalin found
out about these secret meetings and became absolutely
paranoid. He felt the Americans and British were
cutting side deals with the Nazis behind their
backs, maybe even planning to team up against
him. You can see his point. You can. This mistrust
over Operation Sunrise arguably helped set the
stage for the Cold War. Dulles was already pivoting.
He saw the Nazis as the old enemy and the Soviets
as the new one. So he ends the war by alienating
our biggest ally, and protecting a Nazi general.
But before we get to the Cold War, there is another
shadow hanging over this period. The sources
mention Nazi gold. This is where his background
at Sullivan and Cromwell comes back to haunt
him. As the Third Reich was collapsing, there
were serious allegations that Dulles and his
old law firm helped German industrialists move
Nazi funds out of Germany to safe havens in Switzerland
and Argentina. The idea being to preserve their
wealth for a potential post -war comeback. A
Fourth Reich. Essentially. The source material
mentions a connection to Heinrich Himmler's plan
and a business associate of Dulles named Kurt
Baron von Schroeder, who was a Nazi banker. The
allegation is that Dulles and Schroeder created
shell companies to move this wealth to protect
the assets of the very industrialists who had
bankrolled Hitler. Did anyone try to stop this?
Yeah. Or look into it? FBI Director J. Edgar
Hoover tried. He was deeply suspicious of Dulles
and his connections. He wanted to investigate.
But the political pressure was immense and no
formal investigation ever really took off. It's
a very dark, unresolved chapter. It really suggests
that for Dulles, the enemy changed very quickly
from the Nazis to the communists. And he was
willing to use former Nazis and their money to
fight that new battle. It was the ultimate pragmatism
or cynicism, depending on your point of view.
So the war ends. The OSS is dissolved. But Alan
Dulles isn't done. The Cold War is heating up,
and the U .S. needs a new kind of intelligence
agency. And Dulles is right there to shape it.
In 1949, he co -authors the Dulles -Jackson Career
Report. It was a scathing critique of the early
CIA, which had been established in 1947. He basically
argued that the agency was too bureaucratic,
too timid, and needed to be more aggressive,
more capable of covert action. So he writes the
playbook for a more muscular CIA, and then he
gets hired to run the place. Precisely. In 1951,
President Truman appoints him deputy director
for plans. That's the covert ops arm of the CIA.
Then in 1953, the new president, Eisenhower,
appoints him as the director of central intelligence.
He is the first civilian to hold the job. And
this is the beginning of the golden age of the
CIA, if you want to call it that. Or maybe the
Unleashed Age. It was the era of the new -look
national security policy. Eisenhower was a general,
but he wanted to avoid expensive, conventional
wars like Korea. He didn't want thousands of
troops on the ground dying in foreign mud. He
wanted a different way. He wanted to use covert
action and technology to contain the Soviets.
It was cheaper, and it was quieter. Dulles was
the perfect man to execute that vision. Speaking
of technology, we have to talk about the U -2
spy plane. This was Dulles' baby in a way. It
absolutely was. The Air Force had rejected the
design. It was this strange looking thing. Lockheed
called it the CL -282. It looked like a glider
married to a jet engine. The pilots called it
the Angel. The Air Force didn't want it. Why
not? It wasn't a bomber and it wasn't a fighter.
It had no weapons. They didn't know what to do
with it. But Edwin Land, the genius inventor
behind the Polaroid camera, saw its... potential
for high altitude photography and showed it to
Dulles. And Dulles immediately got it. He wasn't
a tech guy, but he understood the value of seeing
over the fence. He saw a way to see behind the
Iron Curtain without risking a bomber crew. He
championed the program, funded it through the
CIA's black budget. The U -2 started flying in
1957, giving the U .S. unprecedented overhead
photos of Soviet missile sites, airfields, everything.
It was a massive intelligence win. For a while.
For a while, until Francis Gary Powers got shot
down in 1960. Which happened on Dole's watch.
A huge international incident. A major embarrassment
because the U .S. initially lied and said it
was a weather plane, and then Khrushchev produced
the pilot and the wreckage, but it sh - shows
Dulles' willingness to embrace new methods. He
wasn't stuck in the past. He was looking for
the next edge. He was also fighting battles on
the home front. We think of the CIA as all -powerful,
but in the 50s they had a formidable enemy in
Washington, Senator Joseph McCarthy. McCarthy
was on his communist witch hunt and eventually
his gaze fell upon the CIA. He wanted to investigate
the agency for communist subversion. And Alan
Dulles was not having that. He viewed the CIA
as his personal fiefdom. Not at all. Dulles knew
that if McCarthy started subpoenaing CIA officers,
forcing them to testify in public, the whole
structure of secrecy would collapse. You can't
have spies testifying on C -SPAN. So what did
he do? So he went on the offensive. And this
is... This is really incredible. The sources
reveal that Dulles ordered the CIA to break into
McCarthy's Senate office. Wait, hold on. I want
to make sure the listener caught that. The director
of the CIA ordered a break in at a U .S. senator's
office. They did. Domestic espionage. They planted
disinformation to discredit him. They fed his
staff fake intelligence about communists in the
agency so that when he went public with it, he
would look like a fool. It was a domestic covert
operation to protect the agency from a domestic
political threat. That is that's shocking. It
really shows how Dulles viewed the agency as
something above the normal rules of democracy,
something that had to be protected at all costs.
He saw it as the Praetorian Guard of the Republic,
and that philosophy extended to his operations
abroad. This brings us to the era of coups. This
is where the gentleman spy becomes the regime
changer. Let's start with the big one. Iran,
1953. Operation Ajax. This is the template for
everything that follows, isn't it? It is. So
Iran had a democratically elected prime minister,
Mohamed Mossadegh. He was a popular nationalist.
He made the decision to nationalize the Anglo
-Iranian oil company, which is now BP. Which
the British were not happy about. They were furious.
They lost their most valuable overseas assets.
So they came to the Americans, to the Dulles
brothers, Allen at CIA, Foster at state, saying
Mossadegh was unstable, a threat that he was
leaning toward the Soviets. Was he actually a
communist? Or leaning that way? Most historians
say no. He was a secular nationalist. But in
the binary black and white world of the Cold
War, if you weren't with us, you were against
us. So the CIA decides he has to go. And the
man on the ground running this is Kermit Roosevelt,
right? Teddy Roosevelt's grandson. That's right.
And the coup they designed wasn't a military
invasion. It was psychological warfare. Explain
that. What did they actually do? They used a
tiny budget, less than a million dollars. They
bribed newspapers to print fake stories and cartoons
depicting Mossadegh as a Jewish stooge or a communist
agent. They hired mobs to riot in the streets
of Tehran, some posing as communists to create
fear, others as pro -Shah royalists to create
chaos. So they created the illusion of a popular
uprising. They manufactured a crisis. They created
chaos in the streets to make it look like the
country was falling apart. So the military had
to step in to restore order. It was political
theater designed to change reality. And there
is this incredible coincidence mentioned in the
source material regarding this code. Yes. So
in August 1953, the coup initially hits a snag.
It looks like it's failing. The Shah of Iran
gets scared and flees the country. He flies to
Rome. And who happens to be checking into the
Hotel Excelsior in Rome at that exact moment?
Alan Dulles. Alan Dulles himself. He was officially
on vacation. He bumps into the fleeing despondent
Shah in the lobby. It's described as pure happenstance.
Am I? I mean, conspiracy theorists and even serious
historians have raised eyebrows at this. The
idea that the head of the CIA just happened to
be at the same hotel as the leader of the country
he was currently overthrowing? It stretches credulity.
He was there to stiffen the Shah's spine, wasn't
he? That's the theory. To tell him to hang on,
that the plan was still in motion. And sure enough,
a few days later, Roosevelt's operation succeeds.
The Shah flies back, Mossadegh is arrested, and
American and British oil interests are secured.
And Dulles is hailed as a hero in Washington.
He did it cheap. fast, and without a major war.
It was seen as a masterpiece of covert action.
So having tasted success in Iran, Dulles looks
at Guatemala the very next year, 1954. Operation
PB Success. Same script, different location.
The target was President Jacobo Arbenz Guzman.
He was another democratically elected nationalist.
He was undertaking land reforms, taking unused
agricultural land and giving it to landless peasants.
The problem was a lot of that unused land belonged
to the United Fruit Company. The largest landowner
in Guatemala. Now we need to clarify the connection
here. Dulles had a history with United Fruit,
right? A deep one. It's a tangled web. Some critics
have claimed Dulles was on the board of directors
of United Fruit. Careful historical examination
suggests he wasn't technically on the board himself,
but his law firm, Sullivan & Cromwell, had represented
United Fruit for decades. His brother, Secretary
of State John Foster Dulles, had also been their
lawyer. So even if he wasn't sitting in the board
meetings, the conflict of interest is just. It's
palpable. He's using the CIA to protect the interests
of his old law firm's biggest client. Absolutely.
The Dulles brothers essentially labeled Arbenz
a communist threat because his policies were
hurting their friends' profits. And the methods
were even more psychological this time. How so?
The CIA set up a clandestine radio station called
the Voice of Liberation that broadcast fake news
into Guatemala about a massive rebel army approaching
the capital. They jammed the government's communications.
They hired a few pilots to fly over the capital
and drop Coke bottles to make whistling sounds
like falling bombs. Coke bottles. And blocks
of dry ice to make loud bangs when they exploded,
they terrified Arbenz into resigning without
a single U .S. soldier firing a shot. It was
a pyrotechnic coup, all smoke and mirror. It
was. And again, it was hailed as another huge
victory in Washington. It kept communism out
of the Western Hemisphere. But looking back,
these operations destabilized these regions for
decades. The Shah's brutal regime in Iran eventually
led to the 1979 Islamic Revolution. Guatemala
descended into a brutal civil war that lasted
36 years and killed hundreds of thousands of
people. So the cheap victory had a very, very
expensive long -term cost. The catastrophic one.
But in the 50s, inside the Beltway, Doles was
seen as a magician. He could make problems disappear.
Until he couldn't. We have to talk about the
Congo in 1960. Tres Lumumba. A very different
situation. This was post -colonial Africa. Lumumba
was the first democratically elected prime minister
of the Congo. He was charismatic, a pan -African
nationalist. And Dulles viewed him as a grave
danger. Why? Was he communist? He was non -aligned.
But he made overtures to the Soviet Union for
aid after Belgium and the U .S. rebuffed him.
For Dulles, that was a red line. He worried Lumumba
would invite the Soviets into the part of Africa
to help with post -colonial development. And
the sources are very specific here. This wasn't
just about regime change anymore. No. This was
an escalation. The sources explicitly state that
Dulles authorized a plan to assassinate Lumumba.
He cabled the CIA station chief in Leopoldville,
saying Lumumba's removal was an urgent and prime
objective. He allocated $100 ,000 to the operation.
And they sent a scientist, didn't they? With
a very specific weapon. Yes. The head of the
CIA's technical division, Sidney Gottlieb, the
same man who ran EmCulture, was sent to the Congo
with a tube of poisoned toothpaste. Poisoned
toothpaste. That was the plan. To infect Lumumba
with a lethal biological agent. Now, that specific
CIA plan didn't materialize. Lumumba was eventually
captured and killed by his political rivals,
with Belgian and likely CIA complicity. But the
intent from Dolezal is clear. He was willing
to order the cold -blooded murder of a foreign
head of state. It's a chilling escalation. But
the real turning point, the moment the magic
ran out and the whole enterprise came crashing
down, was Cuba. The Bay of Pigs, April 1961.
This was the disaster that broke Dole's career.
So set the scene for us. Fidel Castro has taken
over Cuba in 1959. The U .S. wants him gone.
The CIA plan, which actually started under Eisenhower,
was to recruit and train a brigade of anti -Castro
Cuban exiles. They would land at a place called
the Bay of Pigs, spock a popular uprising among
the Cuban people, and overthrow Castro. You're
supposed to be another Guatemala. A cheap, easy
win. Exactly. They thought the people would rise
up, just like the CIA radio stations told them
to. They were supremely confident. But it was
a catastrophe from start to finish. What went
wrong? Everything. First, the elements. of surprise
was lost. Castro knew they were coming. Second,
the popular uprising never happened. The Cuban
people didn't join the invaders. They rallied
around Castro. Third, Dulles had assured the
new president, John F. Kennedy, that if the invasion
failed, the exiles could melt into the mountains
and become gorillas. But he hadn't looked at
a map. The landing site at the Bay of Pigs was
surrounded by impassable swamps. There were no
mountains for miles. That is a staggering oversight.
That's not even spycraft. That's just basic geography.
It is. It was a failure of intelligence at the
most fundamental level. And when the invasion
started to fail, Kennedy got cold feet about
sending in the U .S. military to save them. Kennedy
refused to provide overt U .S. air support because
he didn't want to start World War III over Cuba.
So the exiles were left on the beach. Pinned
down, captured, or killed. The CIA's credibility
was shattered. It was a public humiliating failure
on the world stage. Dulles called it the worst
day of my life. President Kennedy was furious,
absolutely livid. He reportedly said he wanted
to splinter the CIA into a thousand pieces and
scatter it into the winds. That is a famous quote.
And he started by firing the leadership. In late
1961, Dulles and his two top deputies, Richard
Bissell and Charles Cabell, were all forced to
resign. But Kennedy, being a very savvy politician,
did it with a bit of theater. He didn't just
fire him in a memo. No. On November 28, 1961,
Kennedy went to CIA headquarters in Langley to
dedicate the new building. It was a big ceremony.
And in front of the press and the entire staff,
he publicly presented Alan Dulles with the National
Security Medal. It was a face -saving measure,
a very public, thank you for your service, now
please go away. But the relationship was broken.
Dulles wasn't gracious about it in private. Completely
broken. Dulles was bitter. He felt betrayed.
He later told a journalist, that little Kennedy,
he thought he was a god. He couldn't handle the
fact that this young president had ended his
career. He blamed Kennedy for losing his nerve
at the Bay of Pigs and not committing the full
force of the U .S. military. So Dulles is out.
He's retired. He writes a book, The Craft of
Intelligence. He's supposed to be fading into
history. But then, November 22, 1963 happens.
JFK is assassinated in Dallas. And we enter the
final and perhaps most twisted chapter of Alan
Dulles' public life. The new president, Lyndon
Johnson, creates the Warren Commission to investigate
the assassination. And who does he appoint as
one of its seven members? Alan Dulles. The man
JFK fired. The man who privately despised JFK.
It is the ultimate conflict of interest. It's
an appointment that critics have pointed to for
60 years. Why would you put the man who was fired
by the victim in charge of investigating the
murder? It makes no sense on the surface. So
what was the logic or the strategy? Why did LBJ
do it? The prevailing theory, supported by historians
like Stephen Kinzer, is that LBJ put Dulles there
to coach the commission, to be the inside man.
Coach them on what? On how to handle the intelligence
world, on how to interview CIA witnesses, on
what questions to ask, and more importantly,
what questions not to ask. You mean where not
to look. Exactly. You have to remember at this
time, the CIA's attempts to kill Castro, the
mafia plots, the exploding cigars, the poison
wetsuits were some of the deepest, darkest secrets
in the U .S. government. JFK knew about some
of it. His brother, RFK, was deeply involved.
And Alan Dulles, of course, knew everything about
it. So if the commission started digging too
deep into Lee Harvey Oswald's potential connections
to Cuba or to intelligence agencies, they might
stumble on the CIA's own assassination plots
against Castro. Precisely. And that would have
been a geopolitical nightmare. If the American
public found out that their government was secretly
trying to murder foreign leaders, it could have
triggered a war with the Soviet Union or Cuba.
So the theory is that Dulles wasn't there to
find the truth about who killed JFK. He was there
to protect the agency's secrets. And here is
a really surprising detail from the sources.
Robert F. Kennedy, the president's brother and
attorney general, also urged LBJ to put Dulles
on the commission. Which seems insane, right?
Why would Bobby Kennedy want his brother's enemy
on the investigation? But it goes back to the
same thing. Bobby was deeply involved in the
anti -Castro plots, maybe even more than his
brother. He needed someone on that commission
who knew where the bodies were buried, literally,
and would make sure they stayed buried. He needed
a professional secret keeper. And there was no
one better at that than Alan Dulles. So Dulles
served his purpose one last time. He shaped the
narrative. The sources say he was the most active
member of the commission. He was. He attended
the most hearings. He guided the questioning.
He skillfully steered the investigation away
from the CIA. And in the end, the commission
concluded that Oswald acted alone and that there
was no conspiracy foreign or domestic. The CIA's
dirty laundry remained hidden for another decade
until the church committee hearings. It's fascinating
and chilling to think about. The Gentleman's
Sky Ended his career by burying the secrets of
the president who fired him, possibly to protect
the presidency itself from scandal. And he lived
out the rest of his years as this elder statesman
of espionage. He wrote another book, gave speeches.
He died in 1969 of influenza and pneumonia. He's
buried in Baltimore. When you look back at his
entire life, what stands out? He's such a man
of contradictions. He really is. He was a man
who exposed forged anti -Semitic texts and saved
Jewish refugees, but also negotiated with us.
as generals and toppled democratically elected
governments. And he was the gentleman spy in
his public life, but his private life was complicated.
Yeah, very. His own sister, Eleanor, is quoted
as saying he had at least 100 extramarital affairs,
even during his time as DCI. He was a man of
immense appetite for power, for secrets, for
life. He compartmentalized everything. He could
be the pious Presbyterian on Sunday and the ruthless
spymaster on Monday. And he was an interventionist
to his core. He believed that America could not
sit on the sidelines. He wrote a book on it early
in his career. Literally, it was called Can We
Be Neutral? His answer was always a resounding
no. He believed the U .S. had to be in the arena
fighting, even if that meant getting its hands
very, very dirty. He truly believed he was the
good guy fighting the forces of darkness, first
Nazism, then communism. The ends always justified
the means. It leaves us with a final provocative
thought, doesn't it? When we look at the official
history of the Kennedy assassination or the Cold
War in general, how much of it is the unvarnished
truth and how much of it is the version that
Alan Dulles wanted us to see? That is the essential
question. Did his presence on the Warren Commission
fundamentally shape the historical narrative
of the most traumatic event in modern American
history, all to protect the agency's secrets
rather than reveal the full truth? It's a question
that still haunts the corridors of Langley. We
may be living in the world Allen Dulles built,
whether we realize it or not. It certainly feels
that way. Allen Dulles, the man who missed a
call from Lenin, but never missed a chance to
change the world, for better or for worse. A
true and truly complicated architect of the American
century. Thank you for listening to this deep
dive. We encourage you to look closer at the
intersection of intelligence and democracy. It's
a blurry line. And Alan Dulles spent his whole
life walking right on top of it. Indeed. It's
a line we're still trying to find today. See
you on the next deep dive.