Willkie had been a Wilsonian Democrat and early supporter of Franklin Roosevelt. Willkie turned on Roosevelt after his administration created the Tennessee Valley Authority, which he believed provided unfair competition for the public utility company he ran. Commonwealth & Southern Corporation eventually was forced to sell its assets in the region to the TVA in 1939, the same year Willkie officially switched parties from the Democratic to the Republican Party.
Willkie defeated other well-known Republican politicians, including Thomas Dewey and Robert Taft, on the sixth ballot for the nomination in 1940. Beschloss notes that Indiana's former senator, James Watson, warned Willkie at the time that Republicans would not take well to his late decision to switch political parties. "It's all right if the town whore joins the church, but they don't let her lead the church choir the first night," Watson reportedly told Willkie.
Beschloss notes the role the media played in Willkie's unlikely ascension to the Republican nomination. Publisher Henry Luce, whose publishing empire became a major disinformation agent of the CIA regarding the John F. Kennedy assassination, used his magazines, Time, Life and Fortune to help turn the little-known Willkie into a national celebrity at the time. When Willkie arrived in Philadelphia where the Republican convention was being hosted, he boasted that he had self-financed his own campaign. "I will be under obligation to nobody except the people," Willkie said.
Willkie's views on World War II really weren't that much different from Roosevelt's policies of providing aid to the allies, although he pretended to be somewhat of an isolationist in order to win the Republican nomination. He also had no plans to dismantle Roosevelt's New Deal programs; rather, he argued that he could better manage them based on his business experience. After Roosevelt easily defeated him in the November election, he "shed his isolationism as quickly as he had donned it," Beschloss notes. Willkie became much closer to Roosevelt, serving in diplomatic roles for him. He also became a major advocate for a one world government. Willkie was persona non grata in the Republican Party when he briefly entertained a second candidacy in 1944.
Willkie had personal foibles with which to deal as well. He and his wife, Edith, had been estranged for many years. She joined him on the campaign trail in 1940 to quell rumors about their estrangement. Willkie lived primarily in a 5th Avenue apartment in New York City where he carried on an extra-marital relationship with a writer, Irita Van Doren. Decades later, tape recordings emerged of President Roosevelt calling for surrogates to mount a whispering campaign regarding Willkie's marital problems during the 1940 campaign. Roosevelt, of course, was willing to do this knowing he had carried on an extra-marital affair with his personal secretary, Lucy Mercer, for many years. Eleanor Roosevelt apparently had a preference for women and wasn't particularly bothered by her husband's infidelity. Sounds a lot like Bill and Hillary Clinton.