This article takes a worm’s eye view of the National Endowments for the Humanities and the Arts and comments on the political realities that inform their operations. My work as a scholar and an applied theater practitioner with Aquila Theatre received program support from both agencies and has represented them at the White House, US Capitol, and US Supreme Court. I suggest that the traditional division that exists between arts and humanities, as reflected in the policies of both endowments, should be erased for the betterment of public-facing humanities, and, as a humanities program director, I want to address the structural problems of fundraising and the politics of money that inform the granting decisions of these US federal agencies.