In the Soviet Union, top leaders terrified themselves and their population with memories of World War II, and specifically of Adolf Hitler’s surprise 1941 attack on the U.S.S.R. As Benjamin Fischer, an analyst and scholar at the CIA’s Center for the Study of Intelligence, noted: “For decades after the war, Soviet leaders seemed obsessed with the lessons of 1941, which were as much visceral as intellectual in Soviet thinking about war and peace.” Andropov and his colleagues put the KGB on full alert in the early 1980s in response to the lessons they had learned from the Soviet intelligence failures of World War II. It was around that time that Putin entered the KGB Red Banner Institute in Moscow, where Soviet paranoia about the United States and fears of a nuclear war undoubtedly framed the tone and content of his instruction.

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Putin was posted in Dresden, East Germany, by the time Mikhail Gorbachev and Ronald Reagan began a process that would put the tensions and war scares of the early 1980s behind them. He was too low in the KGB rankings to have much interaction with any top-level espionage targets, which would have included Americans. Until he came back from Dresden in 1990 and began working for the mayor of St. Petersburg, Vladimir Putin may have never met an American in any personal context.

By contrast, his position as St. Petersburg’s deputy mayor in charge of external relations offered Putin many opportunities to interact with Americans, in a very different atmosphere from that of the 1980s. After 1991, the Soviet Union was gone, and Putin and the rest of the mayor’s team were trying to figure out how to run the city and make its economy competitive again. American and other Western politicians, as part of a U.S. effort to forge a new relationship with the Russian Federation, openly courted Putin’s boss Anatoly Sobchak, the first democratically elected mayor of St. Petersburg. Putin seemed to respond well to the overtures.

U.S. businesses that moved into St. Petersburg had to deal directly with Deputy Mayor Putin who, according to John Evans, the U.S. consul general in St. Petersburg at the time, was always helpful in resolving contract disputes between U.S. and Russian businesses. Within the city’s U.S. and Western business community, Putin was seen as “pro-business.” He gave no impression whatsoever of any anti-American or anti-Western views.

The St. Petersburg connection also gave Putin an important entry point into the United States. In 1992, Sobchak co-chaired a bilateral commission on St. Petersburg with former Secretary of State Henry Kissinger. It is not clear how much direct contact Putin and Kissinger had at that time. But Kissinger would become an important interlocutor for Putin when he became president later on. Putin has admitted that the source of his initial interest in Kissinger was the former secretary of state’s early career in World War II military intelligence. As a renowned scholar with an academic career and numerous books to his name, Kissinger could provide a sounding board for ideas about geopolitics. He could interpret the United States and the West for Putin. And he could explain Vladimir Putin to other influential Americans. But beyond Kissinger, Putin has had few representative Americans to rely on for insights into how the U.S. political system works and how Americans and their leaders think.