Hentoff has actively pursued the subject of free speech since his first publication on the subject in 1980, The First Freedom: The Tumultuous History of Free Speech in America. The Day They Came to Arrest the Book is a fictional treatment of censorship in schools, a subject he developed more fully in his nonfictional work, Heroes In and Out of School (1987), which tells the stories of ten students who fought for their right to read books of their choice. Most recently, Hentoff's Free Speech for Me— But Not for Thee, analyzes the extreme positions taken by both the Left and Right wings in America.