Jessie was raised in Washington, D.C., more in the manner of a 19th century son than daughter, with her father, who was renowned as the "Great Expansionist," seeing to her early education and introducing her to the leading politicians of the day, an unusual thing for the period. Jessie was very close to her father and stuck by his side. He shared with her the many books and maps in the valise that always accompanied him on their trips to and from Missouri and Virginia. She began, too, to share his dream of a nation stretching from ocean to ocean. In this manner, she became well educated in the ways of social structure and the disciplines of politics, history, literature, and languages. After attaining fluency in French and Spanish, Jessie helped in the translation of government documents.