Recent literature on philanthropy and business has focused on the returns to businesses and entrepreneurs from giving. In this article, we show how historical context impacts the motivations and organizational forms created over time in philanthropic giving that effect and affect such returns. We do this through the prism of the changing ownership structures in the Scotch whisky industry in the twentieth century using an institutional theory lens. In doing so, we capture the story of three sisters who inherited a Scotch whisky business in the 1940s and transformed it into a hybrid philanthropic-commercial vehicle that remains in operation today. We present an extended theoretical model illustrating the interplay of context, motivation, and organizational structure over time on exchanges of capital in entrepreneurial philanthropy.