This Election Day, Wishing for Wendell Willkie

Stanley Weiss
7 min readNov 4, 2020

GSTAAD-I was 13 years old when America engaged in the most consequential presidential election of my lifetime.

The year was 1940. For months, the shadow of Adolph Hitler had grown across Europe, toppling free countries, enslaving free people, and sending Jews to die in camps. By the time the U.S. election began, only Great Britain stood between Nazi Germany and a Europe with swastikas flying over every state capital.

To survive, Britain desperately needed America’s help. It needed our tanks, our planes, and our military supplies to fight Germany on land, air, and sea. But the last thing Americans wanted was to get entangled in another World War.

So, the 1940 Presidential election hinged on one question: should the United States help Great Britain and the cause of democracy in Europe in its hour of greatest peril, or should the U.S. stay out of the fight altogether and ignore the pleas of a United Kingdom that was already on its knees? As I prepare for the second most important election of my lifetime, the story of how that question got resolved has special meaning.

With the hindsight of history, and our memories of the Greatest Generation, the answer seems obvious, but in 1940, it was anything but pre-ordained. In working class neighborhoods like the block in south Philadelphia where I grew up, the U.S. wasn’t pro-German, but it certainly wasn’t anti-German. The idea that the U.S. was going to provide Great Britain what it needed was a long shot at best.

And our elected leaders reflected that ambivalence. The country — as we read every day in the newspaper and heard every day on the radio — was stubbornly isolationist. Almost every American and certainly every leading Republican like my father, a boss for south Philly’s Republican machine, wanted nothing to do with World War II. At the time, I think we really had no idea how horrific Hitler’s Final Solution had become, nor did we believe that the fate of the free world hung in the balance. We had just lost too many friends and neighbors during the brutal trench fighting of World War I.

On the other hand, the Democrats had Franklin D. Roosevelt, who had been in office since 1932 and was the first president in U.S. history to consider running for a third term. The popular FDR believed that the U.S. should come to the aid of Great Britain. Sensing a winning issue, the Republicans wondered who could make the best case against him. For months, three candidates — Gang-busting Manhattan District Attorney Thomas Dewey, Ohio Senator and isolationist leader Robert Taft, and Michigan Senator and foreign policy visionary Arthur Vandenburg — all vied for the Republican nomination. But none felt like they could beat Roosevelt.

But then, seemingly out of the blue, came a young, charismatic farm boy from Indiana, known “as the barefoot boy from Wall Street,” Wendell Willkie. He had first come to public attention during a memorable 1938 radio debate with FDR’s assistant attorney general, Robert Jackson, and followed it in April of 1940 with an even more remarkable appearance on America’s most popular radio quiz show.

1940 presidential campaign poster of American politician Wendell Willkie (1892–1944)

Between those two appearances, Willkie had captured the attention of a few influential publishers, most notably Henry Luce, the publisher of the widely popular magazines Fortune, Time, and Life, who was convinced he could beat Roosevelt. As Susan Dunn has written, Luce put him on the cover of Time in July of 1939 and published a long profile of him in Life in the spring of 1940, which my father proudly brought home. Most significantly, in April, Luce published a short manifesto from Willkie in Fortune, called “We, the People: A Foundation for a Political Recovery.”

Arguing that as a businessman, he could do a better job of running the government than a career politician like Roosevelt, Willkie caught fire at exactly the right moment. Willkie had once been a Democrat, and he was liberal in his views, but he was a Republican. As Willkie biographer David Levering Lewis argues, the manifesto “spoke powerfully to liberal Republicans and disaffected Democrats, to economically sophisticated business interests, (and) conservative midwestern farmers.”

Opening just three days after France surrendered to the Nazis in June, the 1940 Republican Convention was held in Philadelphia, and my father took me along, the first convention I ever attended. My father liked the guy from Indiana. We sat with Willkie’s other supporters, who packed the galleries of Philadelphia’s Convention Hall. I nearly went hoarse chanting “We Want Willkie” with them at the delegates below.

Willkie trailed far behind Dewey and Taft on the first ballot, but then something remarkable happened: Willkie started to climb, pulling ahead on the fourth and fifth ballots. What excited me most was that the home team, the Pennsylvania delegation, finally switched to Willkie on the sixth ballot, well after midnight, giving him the win by one vote. I jumped and cheered like I was at a baseball game and my beloved Phillies had just won a championship.

After he won the nomination, Willkie retreated to Colorado to plan his campaign. When he emerged again in August, the Hoosier did one of the most extraordinary things that any politician had ever done: He decided that Roosevelt was right.

In a speech to 300,000 supporters in his hometown of Elwood, Indiana, Willkie sided with Roosevelt, arguing that if Hitler won and was allowed to rule the Atlantic, it would be a disaster for the United States. While cautioning that young Americans should not be sent to fight and die again in Europe, he called for the U.S. to provide immediate assistance to Great Britain in its fight against the Nazis.

Establishment Republicans were so frustrated with Willkie’s interventionist position that they began to refer to FDR and their nominee together as the “Willkievelt twins.” But Willkie didn’t pull his punches, and on election day, Roosevelt was reelected in a resounding victory.

You would think that a man who had sabotaged his own political campaign and likely political future would go quietly into the night like so many other losing candidates for president. But what Willkie did after the election was maybe even more impressive: in his words and actions, he became a model of bipartisanship, arguing that the future of freedom deserved nothing less.

In an Armistice Day speech a week after the election, Willkie appealed to his fellow Republicans not to “fall into the partisan error of opposing things just for the sake of opposition.” He agreed to travel to Britain on behalf of Roosevelt, where he assured British Prime Minister Winston Churchill that unlike the isolationist views spouted by U.S. Ambassador to the U.K., Joseph Kennedy, the U.S. would help Britain in its time of maximum need.

Willkie then flew back to the US and testified to Congress in support of Roosevelt’s Lend-Lease Bill, to create an “arsenal of democracy” to do just that. As Dunn writes, not only did he eloquently defend the bill with all the charm that won him the Republican nomination, he helped convince 10 Senate Republicans to support the bill, which led to its passage.

Willkie never got to see the end of the story. In October of 1944, shortly before my brother and some of our neighbors fought in the Battle of the Bulge, and six months before I trained to be part of the invasion force of Japan, Willkie died of a heart attack.

Vintage Wendell L. Willkie Campaign Button, Republican Candidate For The 1940 United States Presidential Race, by Joe Haupt

As Americans go to the polls in the second most important election of my lifetime, I’m reminded of Willkie.

As I tick through a list of the thousand and one things I’d like to see the next President of the United States do for our country and the world, what I realize I most want to see is a little bit of the decency, and the courage, and the patriotism that Willkie had, to put his country before his party and himself.

However the election turns out, I’d like to see elected officials from across the political spectrum realize that their fellow Americans are not the enemy — and that taking for granted the leadership of the United States is the surest way to invite its end in a world that is increasingly in short supply of the values for which we all fought seven decades ago.

Then, as now, I want leaders who choose not to immediately “fall into the partisan error of opposing things just for the sake of opposition,” but to remember, as Wendell Willkie did, that there are very few of us who ever get to wear the most precious title of all: American.

Where are you, Wendell Willkie? Now, that we need you. A nation awaits your reply.

Stanley A. Weiss is a business leader and founder of Business Executives for National Security. His memoir, “Being Dead is Bad for Business,” and a collection of selected writings, titled “Where Have You Gone, Harry Truman?” are available online.

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Stanley Weiss

Stanley A. Weiss is a business leader and founder of Business Executives for National Security (BENS).