Lessons Donald Trump Can Learn from Wendell Willkie

Donald Trump won't be the first businessman to snatch the Republican presidential nomination away from seasoned party professionals. That distinction belongs to Wendell Willkie, the party's 1940 nominee.

Willkie and Trump have some things in common.

Both were former Democrats. Trump was a Democrat from 2001 to 2009. Willkie was a delegate to the 1924 Democratic convention and gave $150 to Democrat Franklin D. Roosevelt's presidential campaign in 1932. He switched party affiliations in 1939. "I didn't leave my party, my party left me," he insisted, explaining that the Democrats had become too supportive of big government.

Both were successful businessmen. Trump is a real estate developer. Willkie was president of the electric utility conglomerate, Commonwealth and Southern, from 1933 to 1940. He expanded service and lowered rates. When the Roosevelt administration proposed the Tennessee Valley Authority in 1933 to promote flood control and economic development and generate electricity, Willkie opposed it as unfair government-subsidized competition with private business. He testified against it in Congress and fought it in court. He lost but, always a shrewd businessman, in 1939 sold Commonwealth and Southern's regional facilities to the TVA for $78,600,000, a hefty sum.

Both benefitted from the media. Trump is the author of about 20 books. Willkie had the support of wealthy businessmen and media moguls including Henry Luce, publisher of Time, Life, and Fortune, and other publishers with a large audience. His backers wrote many laudatory articles about Willkie's leadership and Willkie himself also wrote several influential pieces, including "We the People" in the March issue of Fortune, which supported some New Deal programs but criticized Franklin Roosevelt for hostility to business, excessive taxation, and a muddled foreign policy. Trump hosted the reality TV show The Apprentice for 14 seasons. Willkie was something of a radio personality. In January 1938, he debated Assistant Attorney General Robert Jackson on NBC's Town Meeting of the Air, articulating why government should support business. In April 1940, not long before the Republican convention, he appeared on the NBC radio quiz show Information Please, answering questions with knowledge and humor ranging from Matthew Arnold to Nicholas Nickelby to the presidential use of the pocket veto.

Both Trump and Willkie bested the Republican Party establishment and seasoned politicians, but in much different ways. Trump beat all his rivals in the primaries to secure the nomination. There were few Republican primaries in 1940. Willkie stayed out of them and came to the convention in Philadelphia in June as a declared candidate and well-known, highly respected business leader and public figure. The three top contenders for the nomination -- New York District Attorney Thomas Dewey and U.S. Senators Robert Taft and Arthur Vandenberg -- split the committed delegates. None had enough to be nominated. All had negatives -- Dewey was cold and inexperienced, Taft was dull and dogmatic, and Vandenberg thought he should be nominated without actually campaigning. They fought each other at the convention and connived at political deals. For instance, Dewey offered both Taft and Vandenberg the vice presidential nomination in return for their support for him for president; both spurned the deal.

In the weeks before the nomination, the media controlled by Luce and other publishers heaped praise on Willkie. A Gallup Poll just before the convention showed his popularity surging. The convention's arrangements chairman, a Willkie supporter, packed the galleries with Willkie supporters who shouted "We Want Willkie!" on cue. Willkie favored aid to Britain and France in their struggle against Germany while his opponents were isolationists. In a stroke of fortuitous timing for Willkie, Hitler conquered France as the convention opened, giving credence to Willkie’s internationalist stance. Delegates were inundated with thousands of letters and telegrams urging support for their candidate. Many were later shown to be bogus, some generated from phone book names by "Willkie Clubs" across the nation.

Willkie's supporters argued that only their candidate, a fresh personality with new ideas, could defeat the seemingly invincible FDR, whom the Democrats were posed to nominate for a third term. Willkie got the nomination on the sixth ballot.

He had dramatically mastered the Republican Party. Franklin D. Roosevelt confided to an aide that Willkie had strong political appeal and could win. The Democrats mounted an ambitious, well-organized campaign, capitalizing on the president's popularity and his leadership during the Depression and in building up national defense. In November, FDR triumphed, receiving 27,313,945 votes to Willkie's 22,347,744, carrying 38 out of the 48 states, and winning in the electoral college by 449 to 82. Roosevelt carried the traditionally Democratic southern states, urban and industrial areas, and did well among lower and moderate-income voters. It was a decisive victory, but not the landslides FDR had received in 1932 and 1936. A switch of about 5 million votes would have given the maverick Willkie the popular majority.

What could Willkie have done better? His campaign offers five caveats for Trump.

Lesson # 1: Campaign Aggressively

Willkie emerged from his triumph at the Republican convention with high popular interest and support. But instead of capitalizing on his momentum, the candidate relaxed, taking a 5-week vacation in Colorado.

Willkie had spent his early years in Indiana but had been living for some time in an apartment New York's Fifth Avenue in before his nomination in 1940. After his vacation, though, his handlers tried to present him as a small-town Indiana rustic. He delivered a long, rambling formal acceptance speech at his hometown of Elwood, Indiana, on August 17, and then lounged at his Indiana farm for another month before beginning his campaign in earnest. His staff arranged so many informal interviews with reporters that his farm manager quipped, "It's getting so every time the cameraman shows up, the hogs run right over and strike a pose." But the candidate refused to play along, appearing in dark business suits rather than overalls, and one day admitting that "I have never done a stroke of work on a farm in my life and I hope I never have to." Image-makers presented him as a devout churchgoer but one day he admitted to reporters, "I usually sleep on Sundays."

Supporters were dismayed. Henry Luce urged him to "stop this cracker-barrel dawdling" and get on with the campaign.

When Willkie finally got going in September, his campaign was disorganized. Staff on his crowded campaign train, the Willkie Special, was often at loose ends. Willkie was indecisive and his directions often unclear. The candidate travelled thousands of miles on the train, giving speeches along the way, but failed to connect with local issues. Alighting from the train in Cicero, Ill., he began his speech with an attack on Chicago political bosses and, reminded that he was in Cicero, he blurted out "Well, then, to hell with Chicago!" which cost him Illinois votes.

Willkie's speeches were often poorly drafted and unenthusiastically delivered. His voice often became scratchy from too many speeches. His off-the-cuff comments and wisecracks to reporters often revealed inconsistencies or positions at odds with his formal campaign documents.

Lesson # 2: Cultivate Republican Leaders

Trump, like Willkie, has surprised and out-maneuvered the Republican establishment. When he gets the nomination, if Willkie's experience is a guide, Trump needs to repair those relationships.

Willkie slipped and referred to "you Republicans" in his acceptance speech and in campaign speeches called his nomination a "people's movement," implying it was liberation from the party's political bosses. He sometimes referred to himself as a "liberal Democrat." After promising to retain the long-time Republican National Committee Chair, John Hamilton, he reversed himself and replaced Hamilton with House minority leader Joseph Martin, then chastened Martin for telling a colleague that he was headed for defeat.

His campaign manager, Russell Davenport, a former Fortune editor, and staff worked separately from Martin and the Republican National Committee. Willkie contemptuously spurned campaign advice from seasoned party leaders. He disliked schmoozing with local party bosses and sometimes had the Willkie Special parked on railroad sidings outside of cities overnight to avoid having to meet and be photographed with them. In an unguarded moment, he called Republican leaders "boll weevils."

National Republican leaders supported him, but many unenthusiastically. Many state and local leaders, lukewarm at best about the Democrat-turned-Republican at the head of their ticket, worked hard for local candidates but gave limited effort for Willkie.

Lesson # 3: Keep Your Message Consistent

Donald Trump needs a clearer and more consistent message on key issues. Wendell Willkie waffled, and it cost him many votes.

Willkie assailed FDR for breaking the tradition of no third terms for presidents, but in a 1940 article in Look magazine he had written that if the founding fathers had intended that proscription they would have written it into the Constitution. Democrats assailed him with the chant "Better a Third Termer Than a Third Rater!"

Willkie promised to "talk in simple, direct Indiana speech" but often came across more like a dissembling Wall Street lawyer.

He attacked the administration for hostility to business and excessive spending, but weakened his position by endorsing much of FDR's New Deal, including Social Security. He was vague about the policies a Willkie administration would pursue. A political observer noted of one speech: "He agreed with Mr. Roosevelt's entire program of social reform and said it was leading to disaster."

Willkie supported FDR's initiative to begin a military draft in the summer of 1940 and gave tacit approval to the president's deal with Britain to exchange U.S. destroyers for British bases in the Western hemisphere. But toward the end of the campaign, desperate for votes, he flip-flopped on foreign policy, aping the isolationists he had formerly opposed, criticizing the president for signing the destroyers-for-bases deal without Congressional authorization, and asserting FDR was leading the nation into war. Many voters concluded Willkie was an unprincipled opportunist, changing his message to garner support.

Lesson # 4: Keep Your Secrets

Donald Trump's comments about women are already a prominent feature in the campaign. That was not an issue in 1940. But Willkie had been estranged from his wife Edith for years but persuaded her to accompany him on the campaign train and pose with him for photos at campaign rallies. Willkie had a long-running romantic affair with Irita Van Doren, an editor at the New York Herald Tribune. The two remained apart during the campaign but Willkie called or telegraphed her every day. Democrats got wind of the affair and considered exposing Willkie. But Republicans had gotten hold of their own juicy secret -- Democratic vice presidential candidate Henry Wallace had written potentially embarrassing letters to an eccentric religious mystic, whom he addressed as "Guru." Through backroom negotiations between staff of the two parties, both secrets were kept out of the campaign.

Meanwhile, FDR's estrangement from First Lady Eleanor Roosevelt, and his extra-marital affairs, continued to be well-kept secrets.

Lesson # 5: Do Not Underestimate Your Opponent

Donald Trump should not underestimate Hillary Clinton's campaign prowess, particularly after she secures the nomination at the convention and can concentrate full-time on articulating her positions and attack Trump full-time.

Trump can learn from Willkie's 1940 experience. Franklin D. Roosevelt was a consumate politician and shrewd campaigner. He looked "presidential" and an able Commander in Chief by touring military bases and defense plants. A few days before the Republican convention, he suddenly named two prominent Republicans to his cabinet, as the secretaries of War and the Navy, siphoning public attention from Willkie's nomination and making the case that he was building a bipartisan administration to strengthen the nation's military defenses.

He refused to debate, citing his pressing presidential duties.In a late October speech, Roosevelt declared that "We will not participate in any foreign wars," a promise he knew he probably could not keep, but one that effectively undercut Willkie's late-campaign isolationist tilt.

In another speech, Roosevelt pilloried conservative Republican Congressmen Joseph Martin (the new chair of the RNC), Bruce Barton, and Hamilton Fish for opposing New Deal reform measures and voting against much-needed defense appropriations. Democrats took up the euphonious, rollicking taunt of "Martin, Barton, and Fish!" "When I heard the President hang the isolationist votes of Martin, Barton, and Fish on me, and get away with it, I knew I was licked," Willkie said later.

Of course, Donald Trump and Wendell Willkie are much different personalities. So far, Trump seems mostly inclined toward attack and divisiveness, while Willkie was more of a conciliator and unifier. The issues are much different from those of 1940.

But, as is so often the case, history offers guidance, caveats, and insights.