Operation Red Sox | CIA
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While the Americans thought that every single one of their agents was successfully landing, successfully organizing, and successfully leading this broader effort to spark an anti-Soviet uprising in Ukraine, what we now know is that almost every one of these agents, even within the first few days, almost every single one of these Ukrainian agents was flying to their effective death, was flying to doom. Operation Red Sox.

It's 1949. We're in the city of Lviv, in the west of Soviet Ukraine. About 70 kilometers east is Poland, and to the south, the Carpathian Mountains. The highest point of the city is an old ruin called High Castle. From here, you can look out across Lviv and its jumble of roofs, towers, trees, steeples, and cupolas that hang over the city like chandeliers. But if you stood up here in 1949,

you might see something else, something astonishing, charging low through the sky just above the Lviv skyline. C-47 transport planes. They're huge 18,000-pound juggernauts. They call them "sky trains" because of their ability to carry such vast amounts of cargo. And they're not the kind of planes you expect to see just above the rooftops. Least of all here,

But here they are. Not at 5,000 or 10,000 feet, let alone 30,000 feet, but just a few hundred feet off the ground, sometimes as little as 200 feet off the ground. Keep your eyes on these planes and you'll see a string of parachutes open. You'll watch as commandos, trained in the United States by the CIA, tumble to the ground.

These commandos all believe that they're at the start of a crucial mission to undermine Soviet rule in Ukraine. But the reality is, they are very close to the end of their mission

and in many cases, their lives. This was a mission that certainly few Americans were aware of, and this is a mission that continues to haunt the CIA to this day because this was one of the most stupendous failures of the CIA, certainly during the first decade, if not longer, of the CIA's operation. This is Operation Red Sox.

To understand Operation Red Sox, it's important to appreciate the historical context. This mission got started just as the dust was settling from World War II. Much of Europe was in ruin, and two great powers had emerged: the United States and the Soviet Union. During the war, the pair were allies, but in the aftermath, things changed.

It wasn't too soon after the Second World War ended that relations, frankly, almost immediately soured. By 1946, 1947, we see the kind of devolution, the unwinding of relations between Washington and Moscow. You see the discussion turn toward things like an iron curtain as the Soviets clamped down on any kind of democratic or pro-Western movements in newly occupied countries like Poland, like Czechoslovakia, like Hungary. You see this really rapid undercurrent

unwinding, spiraling downward of relation. My name is Casey Michel. I am an author and journalist based in beautiful Brooklyn, New York. And I currently work as the director of the Combating Kleptocracy program at the Human Rights Foundation. An organization that shines a light on how corrupt actors around the world use illicit finances to undermine democracy and strengthen authoritarianism. Casey has also written extensively about Russia and Ukraine.

After the end of World War II, it quickly became apparent that the US and Soviet Union had very different world views and competing interests. The two great powers were at odds.

This is the firmament. This is the universe in which American officials at the newly formed CIA are beginning to discuss how is it they can not only expand American interests, not only expand Western interests in Europe, but how can they beyond that weaken the Soviet grip on central and eastern Ukraine and potentially even destabilize the domestic reality of the Soviet Union itself, which is how they begin discussing what eventually formed into Operation Red Sox

It's also important to understand that, at this time, the US knew very little about what was actually going on in the Soviet Union. Behind the Iron Curtain, the new superstate loomed large in the American consciousness.

But at the time, it was a mystery. It was very, very much a black box that I really don't think we can kind of appreciate looking back from the 21st century given globalized information systems and intelligence gathering. There were

So few American contacts, so few American agents, so few elements of American intelligence gathering in the Soviet Union that, again, it really was this kind of black hole of information about what was taking place in what was suddenly America's primary geopolitical crisis.

competitor, it's tough to overstate how little insight American officials had into what was taking place, not only in Moscow, not only in the Kremlin, but around the USSR itself. I mean, you have to remember the USSR was a gargantuan. It was the biggest country in the entire world, from the Caucasus to Crimea to Siberia to Central Asia, and including Soviet Ukraine, as well as the newly annexed regions like Western Belarus and the Baltics.

I mean, just across this massive landmass, the US had, frankly, almost no idea about what was actually taking place domestically. This dearth of knowledge in the aftermath of World War II was compounded by a lack of an organized intelligence gathering network. It's hard to imagine now, but in the immediate aftermath of the Second World War, there was no CIA.

And the U.S. had no formal network of spies. In short, they had no way to look behind the Iron Curtain. They didn't have anything that was built in in terms of how you could report things, how you could allow American officials insight into what was taking place, whether it's in the Soviet Union, whether it's in sub-Saharan Africa, whether it's in South America. Around the world, there's this great ignorance in Washington about what's taking place in global affairs. The solution to this problem?

The formation of intelligence gathering networks. The Central Intelligence Agency, the CIA, was created in 1947. It succeeded the wartime OSS and the short-lived Central Intelligence Group, formed in 1946. Initially, America modeled the agency on Britain's MI6, the overseas secret intelligence service. Maybe you've heard of it.

The impetus for its formation was the growing tension between the United States and the Soviet Union. And the U.S. government's National Security Council outlined the CIA's responsibilities as follows:

Propaganda, economic warfare, preventative direct action, including sabotage, anti-sabotage, demolition and evacuation procedures, subversion against hostile states, including assistance to underground resistance groups, guerrillas and refugee liberation groups, and support of indigenous anti-communist elements in threatened countries of the free world. The stage was set for Operation Red Sox.

One key figure in developing the mission was Frank Wisner. Wisner was instrumental in supporting various American-backed coups across the globe. He was later involved in toppling regimes in Iran and Guatemala.

But one of his first experiments in revolution took place in Ukraine. He saw this not only as a means of destabilizing the Soviet Union and potentially creating an independent Ukraine itself, but really kind of took this under his own wing as his own kind of pet project that he could point to as an early success, an early kind of proof of concept of what the CIA could do and should do moving forward.

The primary objective of Operation Red Sox was simple: overthrow Soviet rule in Ukraine. And the plan itself was also straightforward. Send a number of Ukrainian separatists, Ukrainian nationalists into Soviet Ukraine to link up with existing anti-Soviet Ukrainian separatist movements and to recruit and organize new members of those movements so that they could stir up

a secessionist movement in Soviet Ukraine to eventually break Soviet Ukraine away from Moscow itself. That was the ultimate strategic goal of Operation Red Sox. The story of Ukraine's historic struggle for independence is long and complicated. Ukraine was under Russian control from the 18th century and was a part of the vast Russian Empire.

They were under the rule of the Tsarist dynasty and then, after the Bolshevik Revolution of 1917, the Communist Party. But in the mid-20th century, a fledgling nationalist movement gathered strength, and it was this groundswell of support for an independent Ukraine that the CIA hoped to galvanize. If Operation Red Sox lit a fuse in Ukraine, the fire might spread to other nations under Soviet rule.

And the mission also had other potential benefits.

One of those, not least of those, is the fact that this separatist movement would require a significant investment, a significant draining of Soviet resources just to fight, just to combat. That Soviet personnel, military personnel, military armaments being directed not at the Americans elsewhere in Europe, but having to be directed at Soviet Ukrainian partisans that are trying to break Soviet Ukraine away from Moscow.

The way CIA officials like Frank Wisner saw it, the mission almost guaranteed success. One early CIA report into the situation in Ukraine, that has now been declassified, read as follows: "Those who have returned to their villages and towns are still considered to be members of the UPA. That's the Ukrainian resistance, even though they no longer actively participate in the resistance activities.

It would, therefore, be comparatively easy to increase the strength of the guerrilla and resistance forces, should the occasion arise. In short, the CIA believed they had an army in waiting, ready to rise up and seek independence for Ukraine. And there were other reasons that Operation Red Sox was expected to be a success.

The difficulties of the Soviet Union protecting such a vast landmass. And the brutal losses they suffered in World War II that had badly broken down Soviet infrastructure. This episode is brought to you by Shopify.

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Even though the Soviet Union was emerging as this economic powerhouse, even though it was emerging as one of the new titans of Europe and obviously one of the key players in the emerging Cold War itself, it was still a country that had been, especially on its western reaches, totally flattened by Nazi Germany and was only just beginning to rebuild. And part of that was they had really no air defense left.

along their Western reaches, including in places like Soviet Ukraine. And I'm not sure how aware the Americans were of that going in, but certainly once they began dropping Ukrainian agents into Soviet Ukraine, they realized they could drop them with absolute ease over and over and over again. And so with high hopes and great expectations, the CIA began to put the plan into practice in the late 1940s.

The first step was to gather Ukrainians who could successfully infiltrate their country on behalf of the Americans. They found them in refugee camps across Europe in the aftermath of the war. I mean, these were, again, ethnic Ukrainians, those who spoke Ukrainian, those who were presumably from the areas and the regions that they were eventually dropped into, especially in western Ukraine itself. And those that beyond that

supported the idea of an independent Ukraine, supported the idea of pushing back against, again, understandably, things like Russian colonialism, Russian imperialism, and Russian control of Ukraine. By and large, they were trained not in the U.S., but in Germany, what eventually became West Germany, by the Americans. And they were trained in a broad range of different tactics, of different tools, different toolkits.

These tactics consisted of ways to disrupt and undermine the Soviets, while also stoking the flames of the Ukrainian independence movement.

Some of the things that they were actually trained in to do was, among other things, identifying Soviet military aircraft, estimating how long runways were, you know, training how to use a parachute, training how to use small arms, training how to actually communicate once they landed, things like Morse code, operating portable radios. So they were trained for

months. I mean, they were trained for, in some cases, up to a year before they were sent in. So if there's one thing that the Americans certainly did successfully in this operation was train these Ukrainian agents and these Ukrainian separatists that were eventually dropped into Soviet Ukraine. By 1949, the CIA had trained close to 100 agents and they were ready to start making drops.

And that's where those huge C-47s, those tanks with wings, come in. They were launched from Central Europe, flown by Hungarian or Czech pilots. And on board, they carried the Ukrainian insurgents. Keen to avoid detection, the huge planes hurtled towards Turkey, then turned north over the Black Sea, flying low enough to be literally under the radar.

They evaded the Soviet radars by flying so low that they weren't detected. When they reached the outskirts of Lviv, the CIA-trained agents started to drop from the sky. So far, so good. And to everyone back at CIA headquarters, including Frank Wisner, that's how it seemed. Things were going well.

It certainly seemed like this was, at the very beginning, perhaps the most successful operation the new CIA had ever undertaken because all of the transmissions they were getting back from these Ukrainian agents that had parachuted out and landed on the ground in Soviet Ukraine, all of them were saying,

Successful drop. Everything is going well. Stay tuned for more information as I continue on my mission, on our mission to spark an anti-Soviet uprising in Soviet Ukraine. This is what the Americans were hearing for the first few weeks and first few months, and in some cases, first few years, that they were successfully executing this incredibly bold plan that in many ways was already going better than they initially thought it might.

Over 5,000 miles away, across the Atlantic Ocean, in the CIA headquarters in Langley, Virginia, Operation Red Sox appeared to be going brilliantly. It's easy to imagine Frank Wisner and his colleagues toasting their success. But on the ground in Ukraine, the reality was altogether different. In fact,

The operation was an unmitigated disaster. While the Americans thought that every single one of their agents was successfully landing, successfully organizing and successfully leading this broader effort to spark an anti-Soviet uprising in Ukraine, what we now know is that almost every one of these agents, even within the first few days, even within the first few weeks,

Almost every single one of these Ukrainian agents was flying to their effective death, was flying to doom, was flying directly into the clutches of Soviet authorities.

Things were far worse than anyone could have imagined. What we know is that about 75% of these Ukrainian agents were almost immediately picked up by Soviet authorities, by Soviet officials. And those that weren't immediately picked up were either never heard from again or took a little bit longer for Soviet officials to find them, to jail them, and then to potentially execute them afterward. So what happened? What went so wrong?

Again, the context is important here. American intelligence networks and the CIA were still in their infancy, remember? But that was not the case in the Soviet Union. They were veterans. And they made the US forces look like amateurs.

If there was a strength of Soviet power projection, it wasn't just the military occupation of much of Central and Eastern Europe, but it was really and truly a global intelligence gathering powerhouse that had no comparison whatsoever, no equal anywhere else. As it pertained to intelligence gathering and espionage, the Soviet Union was leaps and bounds beyond what the Americans could potentially compete with.

Crucially, the Soviet Union had used this intelligence to infiltrate and, for the most part, destroy the

the burgeoning Ukrainian nationalist groups. - They, by the late 1940s, were hollow shells of what they once were. Much of that was because of the success of Soviet intelligence gathering, of Soviet espionage efforts to identify the leaders of these Ukrainian partisan groups and either exile them or arrest them, and then beyond that, help decimate the partisan groups on the ground themselves.

So strong was the Soviet intelligence that it's likely they knew all about Operation Red Sox from the moment the first parachute opened and the first pair of boots touched down on Ukrainian soil. Historian Scott Anderson, author of The Quiet Americans, described the CIA spies as being dropped into "catchment basins." The imagery was clear: they were being airdropped almost directly into enemy hands.

the best idea that we have or the best view of the actual operation as it existed in soviet ukraine itself is that the soviet authorities were aware of every single one of these ukrainian partisans every single one of these ukrainian agents that were dropped which is why they were almost all immediately picked up jailed and then beyond that potentially uh worse the soviets had the cia over a barrel

The severity of the situation was worsened by the fact that the CIA had no idea that they were over a barrel. On the contrary, the first messages that were transmitted back to the US by the Ukrainian spies suggested that everything was going well. But those messages were likely entirely bogus, transmitted by enemy agents with their targets already caught.

The CIA had no idea, the Americans had no idea, and that is why they spent years and years sending these Ukrainian agents, these Ukrainian separatists that they had trained, that the Americans had trained for months, in some cases a year, directly to their death, directly to their doom, without being aware that this was what was actually happening. By the time Operation Red Sox was in motion, it was already much too late.

nationalist movements across countries like Estonia, Latvia, Lithuania and Poland turned out to be hoaxes or controlled by Soviet operatives. But because of those transmissions that spoke of success in the Ukraine and the failings of US intelligence, the planes kept on making the journey across the Black Sea, and the Ukrainian agents kept parachuting into enemy hands.

This was a failure upon failure upon failure that ran for years and years. That the Americans were effectively tricked by their KGB counterparts, their Soviet counterparts, into believing was one of their most resounding successes, even while on the ground, day in, day out, year in, year out.

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Casey believes that it's likely the reason the Soviets were able to so easily crush Operation Red Sox is that they had a spy operating at the highest levels of international intelligence, an MI6 officer with an intimate knowledge of the CIA and how they planned to run this mission. That spy's name? Kim Philby.

Kim Philby is, I think, considered by many to be the most successful espionage agent on behalf of the Soviet Union through the entirety of the Cold War. He was one of the members of the so-called Cambridge Five, which were a group of five Cambridge students that the Soviets successfully recruited in the lead up to the Second World War. Philby was, on many levels, the perfect spy. Suave, debonair, Cambridge-educated,

And when it came to undermining missions like Operation Red Sox, he had form. "Kim Philby, we do know, was involved in identifying hundreds of agents that the West attempted to transport into not Soviet Ukraine but occupied Albania to potentially spark an anti-communist uprising there. So we know Philby and his colleagues were involved in communicating information about similar operations elsewhere.

It's not too much of a leap to imagine them doing the same thing in Soviet Ukraine. — Whether it was undone by Philby or other means, Operation Red Sox was a disaster from start to finish. And therein lies another stain on the burgeoning CIA. It wasn't until the mid-1950s that the airdrops stopped. When assessing the legacy of the operation, one declassified CIA document reported the following:

In the long run, the agency's efforts to penetrate the Iron Curtain using Ukrainian agents was ill-fated and tragic. The airdrop operations did, indeed, prove the law of gravity. There were further controversies that showed themselves when declassified documents shed light on Operation Red Sox.

it became apparent that some Ukrainian nationalist groups, including the Organization of Ukrainian Nationalists, had cooperated with the Nazis during the Second World War. According to one CIA analyst, they were, quote, "Nazis, pure and simple." Casey pushes back on making blanket statements like that.

but explains that, for a long time, the Nazis and Ukrainian nationalist movements had shared goals. And look, when we're talking about Ukrainian partisans, we're talking about a very, you know, a broad brush, a broad array of Ukrainians themselves that were fighting for an independent Ukraine to break away from the Soviet Union itself. But there were a couple primary groups

that were while they were not Nazis themselves, they were not members of the Nazi party. And certainly they did plenty of things that the Nazi regime did not approve of. They were still close allies of the Nazi invaders. And that's for a simple reason that because at the end of the day, what the Nazis wanted was in certain respects similar to what these Ukrainian partisans wanted. And that was the toppling of Soviet power.

For a long time, Operation Red Sox was forgotten about. It was a dark chapter in the CIA's history, one that the agency was not keen to revisit. One of the mission's key players, Frank Wisner, worked on several other high-profile operations, including the U-2 spy plane program.

Perhaps he'd learned a lesson from Ukraine. Why send spies in on the ground when you can do it from the air? You can hear more about the iconic U2 in True Spy's sister podcast, A History of the World in Spy Objects. Wisner suffered a severe breakdown and he retired from the CIA in 1962. He took his own life in 1965.

Kim Philby, the man potentially responsible for sabotaging Wisner's mission, formally defected to Russia in 1963. Philby died in 1988 and was given a hero's funeral. But Operation Red Sox was suddenly relevant again when, in February of 2022, this. On the 24th of February, at dawn, the Russian military launched an invasion of Ukraine.

Troops crossed the border and missiles were launched. Some struck as far to the west as Lviv, the area where many operatives in Operation Red Sox were dropped. The world looked on in horror as news programs across the globe beamed images of the carnage. It was the biggest military offensive on European soil since World War II.

And once again, the United States found itself in a similar situation to the one it faced in the late 1940s. Ukraine is burning. An iron curtain has descended. They want to support an ally, but they don't want to spark a nuclear war. So what do they do?

Casey draws a line between the U.S.'s current strategy and what it tried to achieve almost 75 years ago. As we have seen since February 2022, the Americans, the modern U.S., has finally stepped into the breach to provide Ukrainians with the resources they need, not always in the timeliest fashion, but at least in a continuing fashion, providing the Ukrainians what they need in terms of arms, in terms of funding, in terms of support.

to beat back Russian invaders. Casey believes that you can see the seeds of what that support would look like in Operation Red Sox. When the Americans were flying Ukrainian agents in to link up with other Ukrainian partisan groups, you could argue that what we have seen

in 2022, 2023 is simply the evolution, the expansion of those seeds that were planted by Operation Red Sox. Thankfully, much more successfully in the modern iteration than they were in the 1940s and 1950s, though, again, not nearly as successfully as either Americans or Ukrainians would like them to be

Casey believes that if Ukraine is to be successful in the present-day conflict, it's important to remember what happened all those years ago when the CIA first started dropping agents behind enemy lines in Operation Red Sox. There is a more particular resonance and lesson within Operation Red Sox. And it's not just that Ukrainians will always continue to fight.

for a Ukrainian state, for Ukrainian nationhood, and that the Russian efforts to stamp out Ukrainian identity will ultimately be futile, although that is still a reality, however it might look.

One of the clearest, perhaps the clearest lesson of Operation Red Sox itself, beyond the need for a true intelligence gathering apparatus so you know what's actually happening on the ground, maybe the ultimate lesson is that you cannot just airdrop some folks in and expect them to succeed in sparking a revolution or sparking a resistance movement. There has to also be the boots on the ground coming behind them.

for local forces, local towns, townships, villages, cities, and local partisans to begin rising up. And I think, again, at the end of the day, that's understandable. Those locals don't want to commit suicide. They don't want to immediately pop their heads up only to be shot down. They want to know they are going to have backup in the form of other armies, other militaries, other support coming in behind them.

At the time of recording, the U.S. has spent more than $75 billion providing military and humanitarian assistance to Ukraine.

The Biden administration has provided or agreed to provide Ukraine with battle tanks, anti-aircraft missiles, coastal defense ships and advanced surveillance and radar systems. The U.S. has undoubtedly played a key role in Ukrainian resistance efforts.

And, as Casey suggests, lessons have been learned from Operation Red Sox. You can hear more from Casey Michelle in his new book, Foreign Agents, How American Lobbyists and Lawmakers Threaten Democracy Around the World. I'm Rhiannon Needs. Join us next week for more crucial contact with true spies.