The Lockheed U-2 was the CIA's greatest technical achievement and its most dangerous gamble. Designed by Kelly Johnson's "Skunk Works" at the specific request of the CIA, the U-2 flew so high — 70,000 feet — that no Soviet fighter could reach it, and (it was believed) no radar could lock onto it. For four years, from 1956 to 1960, the CIA flew U-2 missions over the Soviet Union photographing missile bases, nuclear facilities, airfields, and military installations.
The missions produced intelligence that proved the "missile gap" — the idea that the Soviets had vastly more ICBMs than America — was a myth manufactured by politicians and military contractors. Eisenhower knew the U-2 photos showed Soviet weakness. He couldn't say so publicly without revealing the program.
On May 1, 1960, CIA pilot Francis Gary Powers took off from Peshawar, Pakistan, for a mission over Soviet missile sites. The Soviets had developed new radar and a new surface-to-air missile — the SA-2 Guideline — specifically to kill the U-2. Powers was shot down near Sverdlovsk (now Yekaterinburg). He survived, parachuted out, and was captured.
The U-2 incident collapsed the Paris Summit, ended Eisenhower's hopes for a peace agreement with Khrushchev, and handed Soviet propaganda a gift it used for years. It also revealed to the world what the CIA was: not just an intelligence-gathering agency, but an instrument of active operations against sovereign nations — even in peacetime. The fallout directly contributed to Khrushchev's risk-tolerance in deploying missiles to Cuba two years later.
No city was more important to Cold War espionage than Berlin. Both sides had agents everywhere. The city was riddled with tunnels, safe houses, and dead drops. CIA Berlin Base was the most active station in the world — and the most penetrated.
The CIA and MI6 dug a 1,476-foot tunnel under East Berlin to tap Soviet military communications cables. Cost $6.7M. Generated 50,000 reels of tape and 40,000+ transcripts. Unknown to the diggers: British spy George Blake was in the planning meetings. The KGB knew about the tunnel from day one — but let it run for 11 months to protect Blake, then "accidentally discovered" it for propaganda value.
CIA counterintelligence chief James Jesus Angleton, convinced a "Monster Mole" had penetrated the CIA at the highest levels, destroyed careers through paranoid investigations. He paralyzed Soviet operations for a decade. The mole he was looking for — Aldrich Ames — was not caught until 1994, after Angleton's death. Angleton himself was never cleared of suspicion of being a British intelligence mole.
Soviet GRU Colonel Oleg Penkovsky volunteered to spy for the West and delivered over 5,000 classified photographs — including technical manuals for Soviet missiles that allowed the CIA to correctly identify the missiles in Cuba in 1962. His intelligence directly shaped ExComm's decisions during the Missile Crisis. He was caught by the KGB, tried, and executed by firing squad in 1963.
CIA enlisted Cuban official Rolando Cubela to assassinate Castro. CIA officer Nestor Sanchez met with Cubela in Paris on November 22, 1963 — the day Kennedy was shot — to hand over a poison pen device. Cuba's intelligence (DGI) later revealed Cubela had been a double agent throughout. Dulles had approved plots to kill foreign leaders as a routine matter of state.
The largest covert operation in CIA history: $3 billion to arm and train Afghan mujahideen fighting the Soviet Army. Weapons channeled through Pakistani ISI. Among the recipients: Osama bin Laden's network. The Soviets withdrew in 1989. Afghanistan fell into civil war, then Taliban rule, then became the base for 9/11. The CIA's longest shadow operation.
CIA Soviet Division officer Aldrich Ames sold the names of every known CIA and FBI source inside the Soviet Union to the KGB — starting in 1985 for $50,000 cash. At least 10 CIA assets were executed. Ames drove a $60,000 Jaguar on a $70,000 salary. CIA counterintelligence blamed Soviet success on bad tradecraft for 9 years before catching him. He received $2.7M total from the KGB.