Should the United States join forces with Russia and Iran to resolve the continuing bloodbath in Syria? No doubt if Washington entered into a coalition with these authoritarian regimes, many would—rightly—charge America with betraying its core democratic values. But sometimes supping with the devil can become a lifeline.

Great Britain faced just such an unpalatable choice in the period between the two world wars.

Neville Chamberlain, the British prime minister, detested Adolf Hitler but committed his country to paying what he considered an acceptable, if ever-escalating, price to conciliate the Nazi. The benefit, in Chamberlain’s mind, was avoiding another catastrophic war on the Continent. After all, was not Hitler merely trying to “fix” the blatant injustices of the 1919 Versailles Peace Treaty and unite ethnic Germans “stranded” across international borders? Chamberlain’s critics on the Labourite left and even a few on the Tory right demanded an alliance against Nazi Germany with Stalin’s Soviet Union, arguing that Britain could not survive without another powerful ally on the Continent.

Hitler, of course, went on to violate the agreements he signed, consigning Chamberlain and appeasement to everlasting infamy. Yet despite the prime minister’s egregious misreading of the Führer—and his dithering, which worsened Great Britain’s options—Chamberlain’s ultimate nightmare was utterly thinkable: Namely, if Britain had allied militarily with Stalin to stop Hitler, the Soviets might end up occupying the heart of Europe. How in the world would the democracies evict the Communists? Solving one big problem (Hitler) threatened to create another (Stalin). In the event, World War II brought both the necessary alliance with Moscow that Chamberlain had resisted and the Soviet occupation he had so presciently dreaded.

New light is shed on the British predicament by the previously secret writings of Ivan Maisky, the Soviet ambassador to Britain at the time. “The Maisky Diaries: Red Ambassador to the Court of St James’s 1932-1943” offers a distillation of a separate forthcoming three-volume translation of Maisky’s nearly 1,600 pages of dense handwritten and typed entries, which were published in Russian between 2006 and 2009.

The book is deftly edited by Gabriel Gorodetsky, who contextualizes the entries with declassified Soviet and British archival documents. This is a must-read for aficionados of diplomatic history and especially of interwar British high society.

Maisky got launched on a Soviet diplomatic career thanks partly to revolutionary underground connections he made during a stint in London exile (1912-17), and got appointed envoy to the Court of St. James’s in 1932. Readers will discover how Maisky skillfully shaped British government and even public opinion to the benefit of Stalin’s regime. The diaries also show Maisky to have been uncannily well informed about internal British affairs—a strength that, paradoxically, induced his own government to freeze him out and would precipitate his recall in 1943.

Maisky is a skilled writer, and his entries are rendered here in a delightfully fluid translation as he recounts regular conversations with Communist “symps” such as Sidney and Beatrice Webb, H.G. Wells and George Bernard Shaw (who regaled Maisky with racy stories about Karl Marx’s family and maid, as told to him by Marx’s daughter Eleanor before she committed suicide). But the Soviet envoy also had frequent tête-à-têtes with foreign office titans Anthony Eden, Lord Halifax and Lord Simon, among many others, as well as no fewer than five British prime ministers: Ramsay MacDonald, Lloyd George, Stanley Baldwin, Neville Chamberlain and Winston Churchill.
Chamberlain deemed Maisky “a revolting but clever little Jew,” while Tory parliamentarian Henry “Chips” Channon labeled him “the Ambassador of torture, murder and every crime in the calendar.” But they and others in the British establishment accepted invitations to luncheons at the Soviet Embassy at 13 Kensington Palace Gardens and invited Maisky to their own mansions and country estates. Lord Beaverbrook, a right-wing press baron nonetheless eager for good relations with Moscow, commended Churchill to Maisky in 1935, advising that the future prime minister was “without a rival in British politics. I know all about his prejudices. But a man of character who tells the truth is worth much to a nation.”

Churchill and Maisky would cultivate each other assiduously. We see the bulldog cozying up to the Soviet dictator through his envoy on Nov. 16, 1937, when he remarks that Trotsky is “a perfect devil. He is a destructive, not a creative force. I’m wholly for Stalin.” This was hardly personal, for Churchill further noted that “we need a strong, very strong Russia” as a counterweight in Europe and Asia. But with Stalin murdering his own military officer corps at the time, Churchill, Maisky wrote, “began asking me: what was happening in the USSR? Hadn’t the most recent events weakened our army? Hadn’t they shaken our ability to withstand pressure from Japan and Germany?” Maisky lied and reassured him that the Red Army remained strong despite Stalin’s massacres.

Maisky plied his targets with morsels of ostensible inside information and gifts of caviar and flavored vodka, and he took cunning advantage of the animosities among British figures. But sometimes he was taken aback. “How much snobbery there is even in the best English people!” he noted on Oct. 16, 1939, after the social-justice crusader Beatrice Webb told him that “Churchill is not a true Englishman, you know. He has negro blood. You can tell even from his appearance.”

Several important contributions emerge from this book. First, not just leftists but top members of Britain’s establishment forecast the likely demise of market capitalism, clinging to their hopes for some form of British “Conservative socialism.” You cannot properly defend freedom if your faith in it wavers.

Second, notwithstanding the tireless efforts of Maisky and his co-conspirators on the British side, no bilateral grand alliance was possible in the 1930s because neither Chamberlain nor Stalin wanted one. And when the alliance of a democracy and a dictatorship belatedly did come about, following Hitler’s invasion of the Soviet Union in June 1941, it remained hobbled by profound distrust and cross-purposes.

Perhaps the diary’s biggest story concerns the post-World War II order. Although Churchill, unlike Chamberlain, had crucially recognized the Nazi threat for what it was, Churchill, also unlike Chamberlain, failed to fully recognize and pre-empt the Soviet threat already during the war. The mistakes, in both cases, derived from a fixation with British imperial interests. (“Then Churchill spoke of the Middle East,” Maisky records of a meeting on July 3, 1942. “He immediately came to life.”)

The diary descends into tedium as Maisky details the runaround in London between 1941 and 1944 over opening a second front in Europe to alleviate the pressure on the Soviet Union, but he offers shrewd commentary on the consequences of a British strategy to let the Soviets do the fighting against Nazi Germany. “A second front would seem preferable,” he wrote to himself on Feb. 7, 1943. “But is that really the case?” In other words, the debacle of Yalta, which de facto ceded Eastern Europe to Soviet occupying forces, was effectively prepared well before Churchill, Roosevelt and Stalin convened in the Crimea in February 1945.

Diplomacy with the devil can be necessary for a democracy: There is no way Britain and the United States could have stood up to Nazi Germany without the Soviet land army. But strong steps must simultaneously be undertaken to contain the menace of this kind of ally.

As for Maisky, Mr. Gorodetsky acknowledges his grandiosity—the envoy returned to the Soviet Union in 1943 with 70 pieces of luggage, necessitating six 3-ton trucks for the drive from Cairo to the Soviet Union via Palestine, Iraq and Iran—but insists he had “outstanding success.” True enough, except that carrying out his job—penetrating deep into the British establishment—ensured that the paranoid Stalin regime would not allow Maisky to continue doing so.

Ultimately, he was betrayed and broken by the odious system he faithfully served. Arrested in 1953 as an alleged British spy, he spent two years behind bars. Then he begged to be reinstated in the Communist Party and promised, if appointed house historian of Soviet foreign relations, to unmask “the most eminent bourgeois falsifiers.” In fact, with these diaries, he has unmasked himself.

—Mr. Kotkin, a professor at Princeton University and fellow at the Hoover Institution, is the author of “Stalin.”

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