Roosevelt led the United States to victory over Germany and Japan, helped shape the post–World War II world order, and guided the U.S. economy out of the Great Depression in the 1930s. Without a doubt, he was a great president. Yet even in greatness, there were flaws worth examining.

Breaking Tradition: Four Terms in Office

Roosevelt insisted on running for four consecutive terms, breaking the precedent set by George Washington. Washington’s greatness is widely recognized partly because he firmly refused a third term, establishing an informal tradition of two terms (eight years) followed for 150 years. Roosevelt, however, ran for a third and fourth term, which was highly unusual.

The 1940 Presidential Election

Roosevelt moved the Democratic National Convention to Chicago, a city with strong political machines. Though he claimed he would not campaign unless the party drafted him, delegates were swayed by loud broadcasts in the convention hall chanting, “We want Roosevelt… the world needs Roosevelt!” Delegates eventually nominated him overwhelmingly. This is how Roosevelt used spectacle and political pressure to secure his third term.

The 1944 Presidential Election

By 1944, Roosevelt was 62 and already in declining health. Chronic hypertension, emphysema, arteriosclerosis, angina, and end-stage heart disease afflicted him. Doctors warned he might die within six months, whether re-elected or not. Despite this, Roosevelt chose Harry S. Truman, then a relatively unknown senator, as his vice-presidential running mate and won the election with 53% of the vote. Roosevelt’s fourth-term campaign illustrates the extraordinary lengths he went to hold office, even when his mortality was imminent.

As a reaction, in 1951 the U.S. Congress passed the 22nd Amendment, formally limiting presidents to two terms, preventing future third or fourth terms.

Was Roosevelt Indispensable During the War?

Roosevelt is widely hailed as the hero of World War II, but Truman, who succeeded him, successfully completed the defeat of Germany and Japan and managed the postwar world effectively. Thus, Roosevelt’s presence, while influential, was not strictly necessary for Allied victory.

Earlier presidents, such as Calvin Coolidge, had exercised remarkable self-restraint. Coolidge chose not to run in 1928 despite strong public support, humorously noting, “There is no advancement in being president for ten years. Too long.”

Empowering Stalin: A Strategic Mistake

During World War II, Roosevelt made a critical strategic error by empowering Joseph Stalin, giving the Soviet Union a dominant position in postwar Europe.

In 1939, Germany and the Soviet Union publicly signed a non-aggression pact, but secretly agreed to divide Europe. Hitler invaded Poland, and the USSR annexed six Eastern European countries. By 1941, Hitler sought to conquer the USSR, opening the Eastern Front. Roosevelt focused solely on Hitler and Britain, ignoring the threat posed by Stalin and the Soviet communist system.

Had Roosevelt viewed Stalin as a co-enemy of democracy and used the conflict between Hitler and Stalin strategically, the U.S. might have contained Soviet expansion. Postwar reality proved Germany could reform, but Stalin quickly became an adversary, supporting North Korea’s attack on South Korea, backing Vietnam against the U.S., and extending communist influence across the Eastern Hemisphere.

By the end of the war, Roosevelt had begun to recognize Stalin’s nature, criticizing him in March 1945 for breaking promises on Poland, Germany, and war prisoners. Yet, by then, Stalin had already consolidated power, and Roosevelt passed away shortly afterward.

Hoover’s Warning About Roosevelt’s Pro-Soviet Leanings

On June 29, 1941, former President Herbert Hoover publicly criticized any American alignment with the Soviet Union. Without naming Roosevelt, he warned that supporting Stalin would effectively aid the spread of communism in Europe and globally, calling the alliance “more than a travesty—it is a tragedy.” History would later show Hoover’s caution was justified.

A Balanced Judgment

Roosevelt deserves credit for his wartime leadership and domestic achievements, but his pursuit of a fourth term and his misjudgment of Stalin’s ambitions were significant errors.

Score: 50/100

Deduct 5 points for breaking Washington’s two-term precedent.

Deduct 45 points for enabling Stalin, contributing to postwar geopolitical problems and the spread of communism in the Eastern Hemisphere.