This chapter uses J. E. Grunig’s theory as an analytical tool to examine the history of fund raising in the United States and concludes that, historically, there have been four models of fund raising: press agentry, public information, two-way asymmetric, and two-way symmetric. Four models of public relations behavior have been developed by Grunig. First using the concepts of synchronic and diachronic communication in 1976, Grunig introduced four models in 1984 that result from the combinations of direction and balance of intended effect. As with public relations, fund-raising-like activities are as old as civilization itself. Charitable organizations seeking private gifts in the 1800s added special events, or entertainment, to their techniques for attracting funds. The use of entertainment and lotteries, announced through the mass media of that period, parallels the press-agentry techniques of public relations as practiced by historical figures such as P. T. Barnum.