A year after Alicia’s death, Alfred, then 57, married Jessie Ball, a 36-year-old teacher, and moved to Florida. The two had known each other for some 22 years. They first met in the late 1800s, when Alfred traveled to Ball’s Neck, Virginia, Jessie’s birthplace, for hunting trips. A bright woman who was a high-school teacher and administrator in San Diego when she married Alfred, Jessie quickly assumed the role of business confidante and protector of Alfred, who, by the early 1920s, had become almost entirely deaf. After making several trips to Florida on Alfred’s yacht, named Nenemoosha, the duPonts gradually gravitated south.
In 1925 they completed their southward migration and became legal residents of Florida, when Alfred’s cousin, Pierre, was named Delaware’s Tax Commissioner. Loath to allow Pierre to poke around his property holdings and investments, Alfred decided to relocate to Jacksonville, Florida, a city he’d often heard his mother talk about when he was a child.