The best books on American leaders who broke the rules during World War II

In the 1930s, Wendell Willkie was a Democrat who sided with big business and criticized Democratic President Franklin Roosevelt. Then, in a whirlwind, Willkie switched parties and won the Republication presidential nomination in June 1940.

After FDR won the election of 1940, Willkie shattered party expectations again when he called upon Congress to pass FDR’s controversial Lend Lease program to send military aid to European nations facing the assault of Hitler’s Nazi armies. 

Willkie also took a strong stance in support of civil rights. Time and again, he proved he was a leader with a nimble mind unfettered by party politics. He broke the rules by defying those who would predict his politics according to his party affiliation. 

The compelling story of Wendell Willkie and his call for human rights in America and around the world comes to life in David Levering Lewis’s beautifully written biography, The Improbable Wendell Willkie.

In the 1930s, Republicans across America heaped criticism on President Franklin D. Roosevelt’s New Deal programs, which they claimed would wither free enterprise and damage the economy. They labeled him a “socialist”—or worse.

Among the Republicans who broke with this broad Republican assault on FDR was John G. Winant, the Republican governor of New Hampshire. Winant gave up state politics to establish FDR’s Social Security program, and after the start of World War II Winant became FDR’s ambassador to London.

Winant’s courage, first in breaking with his party to join FDR, and then helping Winston Churchill and the British people fend off the Nazi assault, is part of Lynne Olson’s authoritative Citizens of London, the Americans Who Stood with Britain in its Darkest, Finest Hour.

Walter White served as the executive secretary of the National Association for the Advancement of Colored People from 1931 until his death in 1955. A light-skinned Black man often mistaken for white, he used his appearance to infiltrate the white-supremacy power structure and then work for civil rights.

In his evocative autobiography, A Man Called White, White recounts how in 1941 he and civil rights leader A. Philip Randolph pushed President Franklin Roosevelt to take a major step forward in the struggle for civil rights – creating the Fair Employment Practice Committee (FEPC). It’s a gripping tale about an often-overlooked part of the civil rights movement

The FEPC worked to desegregate the war industries, a mission that reshaped American politics and set the Democratic Party on the path of becoming the party of civil rights.

Bill Donovan, recognized as a hero for rescuing his fellow soldiers at the front in World War I, was a rising star in the Republican Party, becoming assistant attorney general under Republican President Calvin Coolidge.

But in mid-1941, when many Republicans were condemning President Franklin D. Roosevelt as a warmonger, Donovan broke with them and supported FDR, urging him to create an intelligence agency to prepare the United States for a war against fascism.

In his insightful Wild Bill Donovan, Douglas Waller recounts Donovan’s bold decision to ally himself with FDR, rejecting partisan politics and instead prioritizing the defense of American democracy. FDR eventually named Donovan director of the Office of Strategic Services, the wartime spy agency that was a forerunner of today’s Central Intelligence Agency.

President Franklin D. Roosevelt and British Prime Minister Winston Churchill, cast together by the rising tide of fascism, became allies to fight their common enemy.

Their politics, however, in some ways stood in sharp contrast. FDR was a liberal Democrat who believed in using the levers of government to help those thrown out of work by the Great Depression. Churchill was a Conservative who had fought many a battle against Britain’s liberals.

Yet the two men broke the rules of rigid adherence to any party. 

As Jon Meacham puts it in his masterful Franklin and Winston, “Churchill changed parties from Conservative to Liberal and back again, and the vicissitudes of his views did not surprise those closest to him.” As for FDR, who built an alliance with prominent Republicans during the war, one associate pointed to the “flexibility of the Roosevelt mind.”