This chapter traces the history of philanthropy and shows the extent to which it is woven into the very fabric of the American entrepreneurial experiment. In order to understand philanthropy as a viable system for recycling wealth and creating opportunity, it is worth probing the dynamics that have sustained philanthropic giving and the conditions under which it has prospered and wavered. After providing a historical background on philanthropy in the United States, the chapter considers the Giving Pledge, an idea put forth by Bill Gates and Warren Buffett that commits billionaires to give away one-half of their wealth in their lifetimes. It then looks at the origins of American generosity, along with volunteerism, associations, and self-reliance. It also discusses mass philanthropy, the welfare state and the persistence of philanthropy, political philanthropy, and the rationale behind philanthropy and charity.