Born in 1853, Jared Flagg was the black sheep of an illustrious New York family. His father, Jared Bradley Flagg, was a noted portraitist and Episcopalian minister who served as Rector of Grace Church, in Brooklyn Heights. His older brothers were prominent, Paris-trained artists in their own right. A younger brother became a famous architect, while another went on to found a major Wall Street brokerage. One of his younger sisters married publisher Charles Scribner, II; another was a member of the famed 400 Manhattan socialites.

Jared, Jr., on the other hand, took to the seamier side of American life, instigating any number of illegal schemes, ranging from leasing furnished flats to facilitate prostitution, to finding chorus line and modeling jobs for pretty but talentless young women, to a phony investment scheme that paid 52% a year, to the sale of worthless bonds backed by heavily mortgaged real estate. Frequently penalized for his criminal and unethical activities by the time of his death in 1926, Jared Flagg barreled his way through Gilded and Jazz Age America, offering a fascinating and heretofore unknown view of how a rising empire evolved at a crucial through crucial eras in its history.