A fact checker from a major magazine wrote asking if Churchill ever declared, “Stalin never broke his word to me.” The short answer is yes. The long answer shows how careful we should be when quoting Churchill.
The original source of this quote is the journalist C.L. Sulzberger (1912-1993), in his 1970 book, Last of the Giants, page 304. Here Sulzberger reports his “five hours with old Winston Churchill” at Chartwell on 10 July 1956.
Stalin never broke his word to me. We agreed on the Balkans. I said he could have Rumania and Bulgaria; he said we could have Greece (of course, only in our sphere, you know). He signed a slip of paper. And he never broke his word. We saved Greece that way. When we went in in 1944 Stalin didn’t interfere. You Americans didn’t help, you know.
Churchill was referring to the much misrepresented “naughty paper,” the “percentages agreement” with Stalin in their Moscow talks (Tolstoy Conference, 9-19 October 1944)—which Stalin did honor. The Soviets made no move to interfere when Churchill flew to Athens to broker a truce between communist and nationalist insurgents, though Stalin was soon meddling in Greece in 1948.
Sulzberger was a reliable reporter, so the source appears valid. As a gauge of Churchill’s attitude toward Stalin, it is more problematic.
By 1956 Churchill was an aged 81, out of power and still smarting over his failure to achieve a summit conference with the Russians (which Eisenhower agreed to almost immediately after Churchill left office, saying privately, that he feared “Winston might give away the store.”) Churchill had long argued for a three-power meeting and “settlement” with the Russians, based on the brand of personal diplomacy he’d practiced with Stalin during World War II.
After the Yalta Conference in February 1945, Churchill said he thought he could trust Stalin. He probably was referring to Stalin’s Yalta promise to allow free elections in Poland. As early as March 1945 he had to admit, in correspondence with Roosevelt, that he’d been wrong. Even in the immediate aftermath of Yalta, on 23 February 1945, he wondered, after Germany’s defeat, “what will lie between the white snows of Russia and the white cliffs of Dover?” (John Colville, Fringes of Power, 563). Speaking at the Massachusetts Institute of Technology (3 March 1949) Churchill predicted the fall of communism, fueled by “a spark coming from God knows where and in a moment the whole structure of lies and oppression is on trial for its life.”
It is fair to say that Churchill believed Stalin had not broken his word through 1944. To some extent his 1956 remark to Sulzberger was meant to contrast what Churchill saw as the giant figure of Stalin. But trust in Stalin was certainly not something Churchill expressed consistently after the war. In the end, I doubt that he had very much.