Willkie was educated at Harvard University, Columbia University and Princeton University. He also graduated from the American Bankers Association Stonier Graduate School of Banking. During World War II, he served as a lieutenant in the United States Navy and was second in command under Commander Weems.
Willkie was president of the Rushville National Bank in Rushville, Indiana, a farmer and cattleman, and a businessman who served on several corporate boards. He was for three two-year terms a member of the Indiana House of Representatives. In 1960, he was briefly considered by Richard M. Nixon as his vice presidential running mate, but the selection went instead to Henry Cabot Lodge, Jr., of Massachusetts.
Willkie supported allowing foreign-trained doctors the ability to practice in small-town America. He also advocated the preservation of the independence of small-town banking.
His professional and social associations included Beta Theta Pi fraternity, the Masonic lodge, Moose International, Benevolent and Protective Order of Elks, Press Club, and the Columbia Club of Indianapolis. He was an admitted to the bar in New York, Washington D.C., and Indiana.
He committed suicide on April 10, 1974. News reports indicated that his suicide followed the early stages of an investigation of the Rushville National Bank by federal regulators. The bank was shut down by the Office of the Comptroller of the Currency in 1992 as insolvent.
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