In 1950, the best friends Jack McAuliffe, Leo Kritzky, and Yevgeny Tsipin graduate from Yale and prepare to go their separate ways; Jack and Leo are recruited to the CIA by Frank "The Wizard" Wisner, and Yevgeny goes home to Moscow, where he is recruited into the KGB by the spymaster Starik while he falls in love with Azalia Ivanova.

At the CIA headquarters in Washington, counterintelligence chief James Jesus "Mother" Angleton begins Vishnevsky's exfiltration and tells his best friend and MI6 liaison, Adrian Philby.

When the KGB and Berlin Police show up to the exfiltration instead of Vishnevsky, Torriti and Jack surmise that the blown defection is because of the mole.

Yevgeny arrives in Washington and manages to tell Azalia that he is in the United States, where he deciphers elaborate Moscow Radio codes at night and delivers liquor during the day, including to the mole: Philby.

Jack escapes and reconnects with Torriti, Wisner has a breakdown over his complicity in the CIA's actions, and Starik tells Nikita Khrushchev of "Kholstomer", his long-term masterstroke to cripple the US economy.

In 1975, Leo is on vacation with his family, Yevgeny visits his dying father along with a disillusioned Philby in Russia, and Jack is working to exfiltrate Kukushkin, who promises information on Sasha.

Angleton feels that Kukushkin may be legitimate, but his obsession with Sasha and Soviet infiltration into the CIA has begun to cripple the Company.

Using information gathered over decades, including Kukushkin's new data and clues from the liquor store where Yevgeny was nearly caught, Angleton divines a system of masterful rhetoric to reveal the mole: Leo.

Leo is freed and Angleton is forced to resign, berating his superiors that the KGB's wilderness of mirrors has falsely convinced them they are winning the Cold War.

The CIA's foreknowledge helps mitigate the damage, but the plan's biggest failure results from Starik underestimating the strength of the US economy.

In 1991, Jack offers Yevgeny an early release from prison if he reveals Leo's location by telling him that Starik sent Azalia to the gulag, but he still has time to find her since the Soviet Union is collapsing.

Tsipin's superior, "Starik" the KGB general, takes posed photos of young girls as a hobby, just like Dodgson.