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17. Dubbed The Ladies’ Man
During his formidable years at the New York Military Academy, Trump was a popular attendee, participating in various school programs, teams, and events. In the NYMA yearbook, as featured in this photo, Donald Trump was brandished as the “Ladies’ Man”. Standing next to an unidentified woman, a youthful Donald Trump is smiling cooly at the camera. With a little research and time, it was discovered the young woman in the photo next to him was the secretary of NYMA at the time, Fran Dunn. Dunn crowned Trump as a “ladies’ man” nearly 50 years before that title became one of his signifiers in the 2016 presidential election.