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.
Putin's rise from that point - with the help first of Leningrad Mayor Anatoly Sobchakand then-President Boris Yeltsin - is another story. He has shown cunning, tactical skill and, at times, statesmanship (in relations with the United States after 9/11, for example) along the way. But he has also shown a disturbing willingness to bet the farm even as his plans come a cropper.
The International Monetary Fund warned last week that Russia's economy will contract by 3.4 percent this year if sanctions remain in place. And the Pew Research Center reported that Russia is now viewed less favorably than the United States in most parts of the world. The image gap is 43 percentage points in Europe (where 69 percent had a favorable view of the United States versus 26 percent for Russia) and 42 points in Africa (United States 79 percent, Russia 37 percent), for example.
Most critically, Putin's regime has reached what Moscow Times columnist Vladmir Frolov last week bravely called a "let them eat cake" phase. Recent public excesses range from Putin's press secretary's multimillion-dollar wedding in Sochi to, as Frolov wrote, a "legally dubious decision to move the 2016 parliamentary elections by three months [that] gives the Kremlin no political advantage while betraying an inner sense of insecurity and weakness . . . . The president's [pursuit of] excessive ratings are turning into a source of political instability."
Moreover, the regime's threat to make a display of destroying European food imports that have found their way into Russia despite an embargo adopted to retaliate for sanctions "flies in the face of Orthodox values and the public sentiment traumatized by a history of famine, war and Soviet scarcity," he continued. The destruction took place on Thursday, by bulldozer, and was nationally televised.
The deepening wounds that Russia has suffered under Putin are almost entirely self- inflicted - a reality that has important implications for U.S. policy.
There are many reasons for the United States to exercise restraint in the Ukrainian crisis. Expecting Putin to reciprocate cannot be one of them. Nor can policy be built on the fear voiced by some strategists that we must accept the permanent neutralization of Ukraine to avoid pushing a weakened Russia into a collapse that would endanger global stability.
Putin's actions will determine how far and how fast Russia continues to sink into isolation and economic decline. The West should adopt a stance of watchful waiting and be prepared for Putin's risk-taking to create new crises along the way.
This is what I conclude from my modest inquiry: It turns out that Putin is not as clever either as I once thought, or as he seems still to believe.