In the immediate aftermath of the Second World War, American authorities realized that their insight into their former allies in the Soviet Union was severely restricted.
This dearth of information stemmed from two primary, related reasons. The first was the lack of any kind of structured intelligence apparatus in the U.S., remedied by the formation of the CIA in 1947. But the second was even more concerning: the lack of contacts inside the Soviet Union, especially in the regions pushing back against Moscow’s rule. And it was that latter issue that only became more salient as the Kremlin began seizing and strangling conquered countries and annexing regions in Europe, including a chunk of Ukraine previously outside Moscow’s grip.
In Washington, the newly formed CIA floated a potential solution. American agents would scour displaced-persons camps across Europe in search of exiles they could train and then secretly smuggle back into the Soviet Union. They would use them to both gather intelligence and link up with other anti-Soviet movements. But some CIA higher-ups wondered why they should stop there. What if the U.S. could also arm these returned figures, and potentially fracture the Soviet Union?
The plan had a couple of things going for it. As one of the few scholarly examinations of the operation detailed, “At the time, Soviet air defenses were terribly unorganized, allowing U.S. planes to violate their airspace with near total impunity.” Moreover, as American handlers saw it, these trainees were hardly landing in a vacuum. If anything, they were effectively jumping into a wildfire: a warzone pitting Ukrainian nationalists against the Soviet authorities trying to hold on to Moscow’s colonial empire. And those Ukrainian nationalists appeared to be winning. For the first time in decades, Ukrainian independence appeared within reach, a message the Americans were happy to reinforce. “The Ukrainian organization offers unusual opportunities for penetration of the USSR, and assisting in the development of underground movements behind the Iron Curtain,” one declassified CIA document from the time reads. And if they could succeed, “ultimately an operational base may be established in… Ukraine.”
The emigres “were being told that all was in the service of liberation, of overthrowing the communist regimes,” Scott Anderson wrote in The Quiet Americans, a book on the early history of the CIA. “That message was reinforced by the constant drumbeat of rhetoric now emanating out of Washington.”
Still, the plan did receive pushback from certain quarters in Washington. As the acting chief of the CIA’s Special Projects Division for Soviet operations wrote in 1947, the U.S. had to “face the fact that in the long run operations using the Ukrainians as an organized group will probably turn out to be worthless — simply because without political support the Ukrainian nationalist groups will be decimated by Soviet pressure and demoralization.” But in those early days of the Cold War, the CIA was looking for an early intelligence success that it could expand elsewhere, especially as relations between Washington and Moscow entered a tailspin during the late 1940s.
By September 1949, the operation was ready, and the first flights launched. Ukrainian commandos successfully crossed into Soviet airspace, touching down in western Ukraine, in heart of the Ukrainian resistance to Soviet occupation. And at first, everything appeared to go well. Messages relayed back to American handlers, via new electronic equipment smuggled behind Soviet lines, talked of operational success. Optimism continued to grow as month after month, drop after drop, the same rosy messages came back.
Yet, back in Washington, concerns started to grow. On the one hand, there was the reality of who these Ukrainian emigres were actually linking up with. The main body of Ukrainian insurgents, and in particular the Organization of Ukrainian Nationalists, had already been linked directly to Nazi atrocities in the region. “They were Nazis, pure and simple,” one CIA operations chief said. “Worse than that, because a lot of them did the Nazis’ dirty work for them.”
Beyond those concerns about enabling fascists, there was also increased understanding of how the Soviet secret police and counter-intelligence operations actually worked — and how little success an operation like Red Sox would likely have in a place like the USSR.
“You’re sending people into these Soviet-controlled areas — Poland or Ukraine or wherever — with the idea that they’re going to start resistance groups or meet up with the ones already there,” one CIA station chief remembered. “But it’s impossible that these resistance groups can exist under the Soviet security system…. It’s a dream. It can’t work. You’re just sending people to their deaths.” If anything, Anderson added, those supposed anti-Soviet resistance groups the CIA thought it was helping support were, in reality, “catchment basins in which the regimes’ enemies, both internal and external, could be concentrated and safely confined until the state was ready to scoop them up.”