I know you will not mind my being brutally frank when I tell you that I think I can personally handle Stalin better than either your Foreign Office or my State Department. Stalin hates the guts of all your top people. He thinks he likes me better, and I hope he will continue to.
President Franklin Roosevelt to Prime Minister Winston Churchill, March 18, 1942, from Churchill and Roosevelt: The Complete Correspondence
I think if I give him everything I possibly can, and ask nothing from him in return, noblesse oblige, he won't try to annex anything and will work with me for a world of peace and democracy.
President Franklin Roosevelt to former Ambassador to the Soviet Union, William C Bullitt, January 29, 1943, from For the President: Personal and Secret: Correspondence between Franklin D. Roosevelt and William C. Bullitt
There are many things President Franklin Roosevelt got right in the run up to, and during, the Second World War. He recognized Germany as a threat, not just in Europe, but globally. FDR also had an ability to spot and promote talent. Selecting George C Marshall as Army Chief of Staff in 1939 was not obvious, as he was promoted ahead of more than three dozen more senior officers, yet FDR did so after Marshall disagreed with him in a large meeting (for the full story read Management Lessons). Marshall proved to be a brilliant choice as was Admiral Chester Nimitz, hand picked by FDR to command the Navy in the Pacific. He also had the good sense to keep Marshall in the U.S. and instead appoint Dwight Eisenhower as commander of Allied forces for D-Day.
FDR also encouraged dissent. The military chiefs and his war cabinet engaged in ferocious arguments at time, particularly from 1939 through 1942. At one point in 1942, Marshall threatened to resign because of his disagreement with the president on the issue of invading North Africa, an issue on which FDR was proven correct - the American army was in no shape to fight the Germans in northwest Europe in 1942, or even 1943. Marshall, who believed military officers should be apolitical and never voted, was initially a doubter about FDR but became an admirer during the course of the war.
Roosevelt exhibited a good strategic sense in the run up and early years of the war, agreeing with the military chiefs that Germany would be the priority in the event of a conflict with both that country and Japan, and in his sense of where American military priorities should be in the critical eighteen months after Pearl Harbor. He also had top notch instincts as to what issues required his involvement and decision making and what didn't.
As I've noted before, in Harry Hopkins he had an informal channel through whom the military chiefs could take issues, trusting Hopkins to decide whether, and how, to make the case to FDR. This stands in stark contrast to LBJ, who in the run up to the Vietnam War, had no such route outside the one channel station operated by Robert McNamara. For a comparison of FDR with LBJ on this issue read Dereliction of Duty.
On the debit side was FDR's obsession with China in the lead up to the war. The military chiefs constantly admonished him for writing checks that could not be cashed, refusing to recognize the weakness of America's position in the Pacific and its very limited ability to do anything to assist China in resisting Japan's invasion. They believed his actions ran the risk of precipitating a Japanese attack on the U.S. would ran counter to the agreed upon strategy of focusing on Germany first. On this the chiefs proved correct.
However, the biggest debit item was FDR's failure to understand the Soviet Union and Josef Stalin and what that meant for his vision for the post-war world. Chip Bohlen, a Soviet State Department specialist who, in 1953, would become Ambassador to the Soviet Union said of Hopkins that "Harry was inclined to dismiss ideology" and the same can be said of FDR. Roosevelt had a vague notion that the American and Soviet systems would, over time, converge in some unspecific way.(1) He believed in personal diplomacy and in his ability to charm anyone. The colonial empires of Britain and France offended FDR and he thought the war should spell an end to them. Why he did not understand the same thing about the USSR, which in that respect was merely a continuation of the land-based colonial empire established by the czars is an interesting question.
That's why even into 1944, when the Allies were clearly winning and the first signs of problems with the Soviets were arising, FDR insisted on continuing lend-lease supplies to the Soviets, including shipping materials that had no obvious short-term value to the war against the Nazis and despite increased evidence of Soviet industrial espionage in America. At the Tehran conference in November 1943 and even more so at Yalta in February 1945, FDR went out of his way to ingratiate himself with Stalin while poking fun and, at times, insulting Churchill. The President simply could not fathom that Stalin was an ideologue and had no deep understanding of communism. He completely lacked an understanding of how the Soviets thought.
To illustrate how different the thinking was let's look at Kim Philby, the Englishman turned Soviet agent who ended up in a senior position in Britain's intelligence agency. Philby would thoroughly betray his country (and the U.S.) leading to the deaths of many East Europeans fighting Soviet tyranny after the war.
After Germany's attack on Russia in June 1941, Philby advised his Soviet handlers that Churchill ordered all British espionage efforts against the USSR to cease, causing the Soviets to wrongly suspect Philby had been turned and become a double agent working for Britain because, in their world, suspending espionage operations made no sense (the U.S., both before and during the war, did not conduct espionage against the Soviets). After all Soviet espionage against Britain and America during the war not only continued, but was expanded. After an extensive investigation of Philby the Soviets concluded that his reporting was accurate.
FDR's obsession with the creation of the United Nations, something not a high priority to the Russians, allowed Stalin to winkle more concessions from the U.S. before grudgingly agreeing to its creation.
Unlike Churchill, FDR remained aloof from Stalin's domination of eastern European countries which became evident during the last months of the war. In August 1944, when the Polish Home Army rose up against the German occupation of Warsaw, while Stalin's forces halted their advance to let the Nazis eliminate the Poles, who they saw as a threat to the communist future plans for that country, Churchill pleaded with Stalin to allow British planes to fly over Warsaw to drop supplies and then land in Soviet territory to refuel, a request refused by the dictator. FDR refused Churchill's request to join the British in making the request to Stalin. For more on this episode read Warsaw Does Not Cry.
Given Roosevelt's death in April 1945, less than three months into his fourth term, we can only be thankful for the big city Democratic party bosses who, in the summer of 1944, rejected FDR's plan to retain Vice-President Henry Wallace on the ticket. The eccentric and naive Wallace was an unwitting tool for the communists and would have been a disaster as president.(2) Instead Harry Truman joined the ticket, becoming FDR's successor and proving a much better post-war president on foreign policy than Roosevelt would have been.
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(1) According to Bohlen, on a return flight from Moscow, on Hopkins last mission to Moscow in June 1945, Harry expressed "serious doubts as to the possibility of genuine collaboration with the Soviet Union", predicting "the American belief in freedom might lead to serious differences."
(2) In 1948, Wallace ran as the Progressive Party candidate for president. He blamed the U.S. for the start of the Cold War and urged America to give up West Berlin in response to the Soviet blockade (for more read Berlin Divides). Several years later, Wallace wrote that he had been deceived during the campaign, later realizing he had been managed by communists.