A novelist by trade whose intellectual capaciousness brought him directly into the field of politics, Mailer is somewhat adrift in the general categories of political analysis we are accustomed to in the United States. For him, the Left was either too blindly ideological or too unfocused; the Right only crafted national sensibility by force; and the liberals in the middle had so far created a world without mountains and valleys, a land hard-pressed to accept the existential longings of the modern individual. Instead of situating himself within these categories, Mailer firmly and repeatedly called himself a “Left Conservative.” He even ran for mayor of New York City in 1969 as an advocate of a “Left Conservative” platform. This chapter will work to define Mailer’s position, situating it amongst other political conversations in mid-century America.