Who knew Russian classics by Chekhov could be the source of grand strategic thinking? Careful study of this playwright and short story writer was but one of the many facets of Cold War polymath George Kennan, whose life and achievements were discussed in a recent lecture at the New-York Historical Society.

In attendance were both Kennan’s son, Christopher, and eldest daughter, Grace Kennan Warnecke.

Paul Kennedy took the podium to introduce his fellow Yale professor, John Lewis Gaddis, author of “George F. Kennan: An American Life” (Penguin Press). Mr. Kennedy said he was going to be short in his introduction, because the last time he introduced his colleague at length to an audience at Yale, Mr. Gaddis began by saying, “In the limited time available to me…”

Mr. Gaddis rolled off a cavalcade of contradictions in Kennan: for one, after convincing the Truman Administration to adopt a strategy of containment, Kennan became “containment’s most severe critic.” He was “an insider who always felt himself to be on the outside,” “a patriot who loved his country but understood another country, Russia, much better than his own,” “an enthusiast for covert operations who came to want to abolish them altogether,” and “a prophet who wound up being profoundly depressed by his own vindication.”

To top it off, while “arguably the most famous grand strategist of his age,” Mr. Gaddis contended, “Kennan much preferred to have been the biographer of Anton Chekhov.”

Mr. Gaddis went through a list of many, varied aspects of Kennan that he would not be addressing that evening: Kennan’s career in the foreign service, as ambassador, as historian, as environmentalist, as poet, as Christian. There were still more.

Mr. Gaddis said he had been Kennan’s biographer for three decades. “I was Kennan’s Boswell longer than Boswell was Johnson’s Boswell,” said Gaddis, to audience laughter.

The main thrust of Mr. Gaddis’s lecture involved showing how under-examined was Kennan’s ability to draw strategic insights from great classical works.

Mr. Gaddis discussed Kennan’s famous anti-communist article in the journal Foreign Affairs, “The Sources of Soviet Conduct,” that argued for containment of the Soviet Union. Although signed anonymously as “X,” Kennan’s authorship was known a week or so later since he was the only one in foreign policy circles known refer to figures such as Edward Gibbons and Thomas Mann.

Mr. Gaddis said that literature such as this helped form the basis for Kennan’s noted prognostication that “the Soviet Union would in time destroy itself from within” since behind “a formidable external facade contained internal enfeeblement.”

Mr. Gaddis said Kennan had time to read great literature while on long transatlantic flights during World War II, since they were too loud to have conversations.

Mr. Gaddis said Kennan took from military author von Clausewitz three key notions: first, war is the furtherance of policy by other means (Kennan noted that the Soviets saw no difference between war and policy). Second, military operations should be proportional to their intended goal; and third, there is worthiness to defense because “every offensive in time exhausts itself .”

Kennan drew from the historian Edward Gibbon the understanding that the Soviet Union, like Rome, had expanded too far and that an empire cannot grasp territory indefinitely against the will of its various populaces.

Kennan’s affection for Chekhov was supreme. Mr. Gaddis told how Kennan quoted Chekhov at a lecture to students at Yale in 1946 about “the well-meaning owner of an estate who tried to befriend its peasants in order to reform their lives but had got nowhere with them.” The dejected mistress is told that getting people over to your side takes time, like sowing grain on a rocky area that must be cleared and continually tended to and plowed. It is “just the same with people,” Gaddis read, “you have to keep after them and keep after them and then you can win them over.”

Mr. Gaddis said that Kennan was making the point that “people could reshape even the most tyrannical governments, but this would take time,” noting that “circumstances, not sentimentality, would shape people.” Mr. Gaddis averred that this was the key aspect of Kennan’s notion of containment of the Soviet Union: “It was to create the circumstances over time that would leave the leaders of the Soviet Union no choice but to reshape their country…to keep after them until you won them over.”

Toward the end of the lecture, Mr. Gaddis turned to discussing farming and horticulture, both real and metaphorical. He quoted Kennan’s view: “We must be gardeners and not mechanics in our approach to world affairs.”

“More than anyone else, in mid 1940s,” Mr. Gaddis continued, Kennan “showed that one need not resort to the extremes of either war or appeasement, in dealing with the challenge posed by the Soviet Union.” “With patience,” as Kennan viewed it, “there could be a third way.”

Mr. Gaddis spoke of how agrarian-inclined Kennan bought a farmhouse outside of (the “improbably named”) East Berlin, Pennsylvania, that recalled for Kennan houses on Russian estates.

Mr. Gaddis contrapuntally turned next to Chekhov at his villa in Yalta, at the end of his life, expiring from tuberculosis. Chekhov, who died the year Kennan was born, planted a garden there that he was aware he would never witness fully blossom.

Mr. Gaddis contended that Kennan “lived to see the seeds he planted in the 1940s . . . vindicate him in the 1980s and 1990s.”

“Chekhov, of course, was not that fortunate. He did not live to see the seeds he planted a hundred years ago grow into the great garden at his dacha.”

“But I like to think,” concluded Mr. Gaddis, reaching a poignant note, “that one or two of the seeds Chekhov planted so long ago actually took root in the mind of Chekhov’s failed biographer, George Kennan, with the result that the two of them collaborated with, what seems to me, surprising success in the saving of Western civilization.”