Winnaretta Singer-Polignac, as befitted a future princess, was born in The Castle, a sumptous mansion situated on a hundred acres of parkland perched above a river. The Castle boasted room after room filled with the most elegant and costly furnishings that money could buy. A battalion of servants bustled through the house, attending to the needs of family members and guests. The large stable contained, in addition to horses and sleighs, a canary-yellow carriage that could transport thirty-one people.

What was unusual about the Singer Castle was its location: not in Sussex, or the Loire Valley, or in Bavaria, but in Yonkers, a northern suburb of New York City. Winnaretta's parents were not royalty, and in fact both came from humble backgrounds. And yet both father and mother came to be known in every corner of the globe—he for his family name, which was seen in millions of households, emblazoned on the machine that he had perfected and manufactured, the Singer sewing machine; she because of her beautiful face, which was rumored to have inspired sculptor Frédéric Bartholdi in creating the Statue of Liberty, the world's most visible woman. How could a child grow to equal—or surpass—such parents?

Winnaretta Singer was her father's twentieth child. In all, Isaac Merritt Singer would father twenty-four children from two legal and three common- law marriages. Although he would disavow all liaisons prior to his marriage with Winnaretta's mother, Singer acknowledged every single one of his children by name in his will and left each of them a handsome bequest. Like Paul Bunyan of American folklore, Isaac Singer lived a life of fantastic, even mythic proportions. His life bespoke big dreams, outsized curiosity, bold actions, enormous wealth, and huge appetites.

Winnaretta's godfather was Edward Harrison May, the English-born, French-trained American artist, best known at that time for his contribution to the 1851 “Grand Moving Panorama of the Pilgrim's Progress.” Moving panoramas were paintings hundreds of feet long, unrolled across a stage in “scenes.” Their stories, travelogues or epic tales, were accompanied by narration and music. These mid-nineteenth century “blockbusters” of visual art toured from city to city, attracting thousands of paying spectators, earning May over $100,000. He and Singer had been friends for years.