It was the very strength of the British ruling class—its ability to turn out successive generations of tough, resourceful and largely honorable soldiers and statesmen like the Duke of Wellington, Lord Nelson, the elder and younger Pitts, Lord Palmerston, William Gladstone and even an exotic transplant like the Jewish-born (but hastily christened) Benjamin Disraeli, along with legions of dim but dutiful upper-class twits—that left it prone to betrayal from within once old certainties and loyalties began to falter. If there was a measure of truth in Wellington’s apocryphal quote that the Battle of Waterloo had been won on the playing fields of Eton, the world—and the confident worldview—that victory had represented began to dissolve a century later in the mud and slaughter of World War I. At war’s end, the superficial structure of Britain’s ruling class still stood and the empire it ruled over was larger than ever. But the unquestioning faith of the governing class in itself and its imperial mission had been shaken to the core. Leaders like Winston Churchill, old enough to remember Victorian glory at its height, remained true believers. But the generation that had served in the trenches, both as officers and privates, would never be quite so certain again. And a few of them—along with some of their younger siblings—would trade their blind faith in the old imperial order for blind faith in the heroic myth of the new Soviet order.

THERE IS no evidence that Kim Philby had a real working knowledge of Marxism-Leninism or that he even found it very interesting. But he seems to have viewed the Kremlin as an elect—the sanctum sanctorum of a new elite, an exclusive, secret circle that would one day rule the whole world. And, at an early age, he decided he wanted to join it. Recruited to Marxism at Cambridge and clandestinely married to an Austrian Communist he met on a visit to Vienna just after college, Philby’s gift for duplicity served him well. He won an award for bravery from Francisco Franco as a foreign correspondent covering the Spanish Civil War, though he secretly supported the Communist-backed Spanish loyalists.

Thanks to his Cambridge degree and his father, Harry St. John Philby—a distinguished if highly eccentric savant, Arabist and imperial adventurer with strong establishment connections—Kim had all of the social assets needed for entry into the pre–World War II British intelligence establishment. Once in, there was no stopping him. By the time World War II was over, Philby had been awarded the Order of the British Empire for his wartime services—alongside a secret medal from the Soviets—and was “increasingly seen by his colleagues in British intelligence as a man marked out for great things.” His standing was best summed up by the historian and former intelligence officer Hugh Trevor-Roper:

I looked around at the part-time stockbrokers and retired Indian policemen, the agreeable epicureans from the bars of White’s and Boodle’s, the jolly, conventional ex-Navy officers and the robust adventurers from the bucket shop; and then I looked at Philby. . . . He alone was real. I was convinced that he was destined to head the service.

But, then and later, judging what was “real” was never Trevor-Roper’s strong suit. In his later years, in return for a hefty retainer, he would “authenticate” a set of clumsily forged Hitler diaries, once more mistaking a fake for the real thing.

By the time Philby was finally exposed and fled to the Soviet Union in 1963, he had wrecked the lives of his second and third wives as well as the career and mental health of James Angleton. Even in Soviet exile he maintained his flair for betrayal:

Philby rekindled his friendship with Donald Maclean and his wife, Melinda, and the two exiled couples were naturally thrown together. Maclean spoke fluent Russian and had been given a job analyzing British foreign policy. He often worked late. Philby and Melinda started going to the opera and then on shopping trips together. In 1964 Eleanor [Philby’s third wife, who had accompanied him into exile, although she had played no part in his treason] returned to the United States to renew her passport and see her daughter [from a previous marriage]. In her absence Kim Philby and Melinda Maclean started an affair. It was a fitting liaison: Philby was secretly sleeping with the wife of an ideological comrade and cheating on his own wife, repeating once again the strange cycle of friendship and betrayal that defined his world.

It is comforting to know that by the time he died in a Moscow hospital on May 11, 1988, Philby must have realized that he had joined the wrong club and bet on the losing team. The Berlin Wall hadn’t come down yet, but the old Soviet order was crumbling all around him.

Yet it is just possible that, in his closing Moscow years, Kim Philby chalked up one more win for his side. In a 1986 conversation with John le Carré, himself an MI6 veteran, Nicholas Elliott, who had survived his friendship with Philby less singed than most, offered a number of useful insights into his erstwhile friend and betrayer, all recounted by le Carré in a highly amusing afterword to A Spy Among Friends. Speculating on what kind of advice Philby had given his Soviet hosts, Elliott was emphatic:

One of the things Philby has told them is to polish up their goons. Make ’em dress properly, smell less. Sophisticated. They’re a totally different-looking crowd these days. Smart as hell, smooth, first-class chaps. Philby’s work, that was, you bet your boots.

Who knows? Vladimir Putin, the Russian Federation’s leading former KGB agent, may be the living embodiment of Kim Philby’s legacy of betrayal.

Aram Bakshian Jr. is a contributing editor to The National Interest and served as an aide to Presidents Nixon, Ford and Reagan.