Once upon a late-October evening in antebellum New York City, Martha Bulloch Roosevelt bore her second child, an eight-pound baby boy named Theodore. “Teddy,” Martha and Theodore Roosevelt Sr.’s first son, entered an affluent, old New York family whose wealth was produced by the family’s multi-generational import-export firm. Theodore Sr., known both for his piety as a philanthropist and his boorishness at New York society balls, had already risen to the ranks of the city’s elite by Theodore’s October 27, 1858 birth. Five years his junior, twenty-two year old Martha “Mattie” Roosevelt was the daughter of a wealthy Georgia planter.