This chapter examines the Ford Foundation’s predominantly economics- and finance-based expertise, and the way it sustained the country’s largest and most expensive performing arts institutions: orchestras, operas, and conservatories. Ford accomplished its goals primarily through matching grants and endowments, hoping with matching requirements to diversify organizations’ funding sources and expand the public’s commitment to local arts. Based on the expert advice of economists and administrators, Ford intended endowments to be a permanent source of income for orchestras and conservatories, if they managed the invested principal properly. In practice, however, wealthy individuals on boards of trustees for institutions such as the Boston Symphony Orchestra and the Juilliard School solidified their personal, social connections to elicit five-, six-, and sometimes seven-figure gifts. In general, ordinary citizens and the local community did not participate, and as a result, broad-based support never materialized. Orchestras and conservatories came back knocking on the foundation’s door again and again.