One of the most complex spy swaps was negotiated in 2023 involving 10 prisoners and the release of 6bn in Iranian oil money.

In a breathtaking Cold War exchange, American lawyer James B. Donovan helped the CIA facilitate the exchange of KGB Colonel Rudolf Abel for the Soviet-captured American U2 spy plane pilot Francis Gary Powers. Berlin’s Glienicke Bridge was the tense location for the 1962 prisoner exchange - a moment immortalized in Tom Hanks’ Bridge of Spies - but the swap of Abel for Powers and a Yale student named Frederic Pryor wouldn’t be the last or largest ‘spy swap’ in history. 

Here are some of the more notable prisoners who’ve featured in the exchanges.
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The US-Tehran swap (2023)

Tehran released five American prisoners in a complex prisoner swap on September 18, 2023, that involved 10 prisoners and the release of $6bn of Iranian oil money reportedly transferred from South Korea to Qatar. The delicate diplomatic negotiation - with Qatar acting as the middleman - was criticized by Republicans. But families of the Americans described the US prisoners as hostages held on false charges so Iran could use them as bargaining chips. The Americans accused of spying on Iran include four men and a woman, the BBC reported. They included: Morad Tahbaz, 67, an environmentalist with US, British, and Iranian citizenship; American-Iranian businessmen Siamak Namazi, 51, and; American-Iranian Emad Shargi, 58. All were held in Tehran’s notorious Evin prison on espionage charges. The identities of the fourth and fifth released prisoners were not immediately undisclosed. The US also released five Iranian prisoners in addition to the money.

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Operation Ghost Stories, the sleeper agent spy swap (2010)‍

Days after the US arrest of 10 Russian ‘sleeper’ agents in 2010, CIA director Leon Panetta reportedly called Russia’s SVR spymaster Mikhail Fradkov to propose a spy swap, the largest since the end of the Cold War. The daylight exchange on the tarmac at Vienna’s airport captured the world’s imagination with stories of ‘sleeper spies’ in the suburbs. The US released 10 Russians arrested in Operation Ghost Stories, including Anna Chapman, the honey trap spy and sometimes lingerie model. In return, Moscow released four people including Sergei Skripal, a Russian military intelligence officer poisoned by Novichok in 2018.
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The Swingers’ spy swap (1986)

Czechoslovakian and KGB spies Karl and Hana Koecher were part of a nine-person spy swap at Glienicke Bridge in 1986. Karl, a linguist and CIA translator/analyst, and his wife gathered kompromat on US spies at swingers’ parties and nudist beaches. Hana wore a white mink hat and fur coat to the spy swap. A gold Mercedes whisked them away from the bridge and Karl recalled drinking champagne before flying back to Prague for a two-month interrogation. In exchange for the agents, the Soviets released Anatoly Shcharansky and other dissidents.

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Alan P. Gross, the spy swap that wasn’t (2014) 

Maryland’s Alan Gross spent five years in a Cuban prison accused of being an American spy rather than a USAID contractor. Havana freed Gross in 2014 as part of a deal that paved the way for the loosening of US-Cuban economic and travel relations. The talks were facilitated by former US President Jimmy Carter, Canadian negotiators, and even Pope Francis. Three Cubans - all convicted of spying as part of Florida’s so-called Wasp Network - were released around the same time although some American officials maintained the timing of the releases were purely coincidental.

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Taiwan and China swap (2015) ‍

News of the first spy exchange between China and Taiwan emerged in 2015 when the Taipei press revealed the release of Li Zhihao, a mysterious Chinese intelligence officer known as ‘the man in black’ who’d been serving a life sentence in Taiwan. In return, Beijing reportedly freed Chu Kung-hsun and Hsu Chang-kuo, two Colonels in Taiwan’s Military Information Bureau, who were arrested a decade earlier. The BBC described the swap as a mutual gesture of goodwill ahead of talks between leaders of both countries.

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The Daniloff-Zakharov swap (1986)

In one of the more curious Cold War exchanges, Gennadi Zakharov, a Soviet physicist who worked for the UN, was arrested in an FBI sting operation in 1986. One of Zakharov’s former students, a Guyanese man, met Zakharov at a New York subway station and handed over classified documents describing US Air Force jet engines in exchange for $1,000 cash. The FBI pounced. Three days later, the KGB arrested American journalist Nicholas Daniloff in Moscow and charged him with espionage. After robust discussions between Washington and Moscow, the prisoners were released one day apart without charge and were allowed to leave the country. 

The Portland Spy Ring (1969)

Intriguingly, the CIA helped uncover a KGB spy ring in London after a tip-off from a Polish agent codenamed ‘Sniper’. The plot involved Harry Houghton, a clerk in Britain’s Underwater Detection Establishment in Portland, England. Houghton and his lover, Ethel Gee, sold intel about Britain’s nuclear submarine program and were part of a larger spy ring along with Morris and Lona Cohen (American-born KGB agents posing as Peter and Helen Kroger) and a KGB agent named ‘Gordon Lonsdale’. The UK and Soviets struck a deal and the Cohens were shortly en route to a stop-over in Poland in exchange for jailed lecturer Gerald Brooke. Gee and Houghton were imprisoned.

The Wynne-Lonsdale spy swap (1964)

‘Gordon Lonsdale’, the KGB handler who facilitated Britain’s Portland Spy Ring, was operating under the cover of a multi-millionaire Canadian playboy running a jukebox and bubblegum machine businessman. In reality, Lonsdale was KGB agent Konon Molody, who was imprisoned in the UK and swapped for Greville Wynne, the naive British businessman portrayed by Benedict Cumberbatch in The Courier. Wynne was the middle-man. He delivered high-level military intel from Soviet GRU Lt. Col. Oleg Penkovsky to Western powers, which helped avert the Cuban Missile Crisis. In 1964, Wynne and Molody were swapped in Berlin. Penkovsky, meanwhile, was executed. 

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The largest-known spy swap (1985)

Berlin’s Glienicke Bridge was once again the backdrop for the largest-known prisoner exchange in 1985. Twenty-five Americans held in East Germany and Poland were swapped for four others - three Soviets arrested in the West plus Polish agent Marian Zacharski. Zacharski was sent to California by the Polish government, then an Eastern bloc country working in concert with the Soviet Union, to uncover military and industrial secrets in the aerospace industry.