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He was born in New York City on September 5, 1873 to Alice Claypoole Gwynne and Cornelius Vanderbilt II.
He was educated by private tutors at St. Paul's School in Concord, New Hampshire before attending Yale University where he graduated with a Bachelor of Arts degree in 1895.
Against his father's wishes, in August 1896 he married Grace Graham Wilson, the youngest child of New York banker Richard T. Wilson, Sr.
Remaining at Yale until 1899, he earned a Bachelor of Philosophy degree and, having a great deal of interest in the mechanical and engineering aspects of his family ’ s railroad business, he also earned a degree in mechanical engineering.

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