That moment led me to other conversations, over a matter of months, with U.S. and European intelligence operatives who had studied the Russian president's 17-year KGB career. They too traced a portrait of Putin as a failed spy who was being squeezed out of the KGB when the Soviet system collapsed and political connections suddenly offered him a route to power.
"He was seen in the system as a risk-taker who had little understanding of the consequences of failure," one said. "The KGB of that era was not keen on risk."
That analysis of Putin, rather than one of him as a master spy, fits more closely with what he has done as Kremlin boss. Putin today displays an open contempt for Russian public opinions and an uncaring disregard for the economy-damaging sanctions and international disapproval that his Ukraine adventure has provoked, traits that befit a drunken gambler.
When I pressed for details on Putin's time as a spy, I was pointed to the fact that he was given a backwater assignment in Dresden rather than in the East German capital in 1985, and then was sent to do counterespionage in Leningrad rather than Moscow at the end of that tour.
"It was a message that he should seek another career," said one of the operatives, all of whom insisted on anonymity and discretion about where and when our conversations took place.