In the summer of 1968, Mailer covered the Republican and Democratic conventions in Miami and Chicago, respectively. In this work, as in Armies of the Night, Mailer employs the literary tactics of New Journalism, and includes himself as a character in the narrative. Yet the Mailer of Miami and the Siege of Chicago is different from the Mailer of The Armies of the Night. In addition to providing the historical and political context for the publication of this work, this chapter will discuss the shift in Mailer’s level of involvement, enthusiasm, and support for the protests that erupted in Chicago.