The group Ayers headed in Detroit, Michigan, became one of the earliest gatherings of what became the Weathermen. Before the June 1969 SDS convention, Ayers became a prominent leader of the group, which arose as a result of a schism in SDS. "During that time his infatuation with street fighting grew and he developed a language of confrontational militancy that became more and more pronounced over the year [1969]", disaffected former Weathermen member Cathy Wilkerson wrote in 2001. Ayers had previously been a roommate of Terry Robbins, a fellow militant who was killed in 1970 along with Ayers' girlfriend Oughton and one other member in the Greenwich Village townhouse explosion, while constructing anti-personnel bombs (nail bombs) intended for a non-commissioned officer dance at Fort Dix, New Jersey.
In 2001, Ayers published Fugitive Days: A Memoir, which he explained in part as an attempt to answer the questions of Kathy Boudin's son, and his speculation that Diana Oughton died trying to stop the Greenwich Village bomb-makers. Some have questioned the truth, accuracy, and tone of the book. Brent Staples wrote for The New York Times Book Review that "Ayers reminds us often that he can't tell everything without endangering people involved in the story." Historian Jesse Lemisch (himself a former member of SDS) contrasted Ayers' recollections with those of other former members of the Weathermen, and claimed that the book had many errors. Ayers, in the foreword to his book, stated that it was written as his personal memories and impressions over time, not a scholarly research project. Reviewing Ayers' memoir in Slate Magazine, Timothy Noah said he could not recall reading "a memoir quite so self-indulgent and morally clueless as Fugitive Days". Studs Terkel called Ayers' memoir "a deeply moving elegy to all those young dreamers who tried to live decently in an indecent world".
Much of the controversy about Ayers during the decade since 2000 stems from an interview he gave to Dinitia Smith for The New York Times on the occasion of the memoir's publication on September 11, 2001. The reporter quoted him as saying "I don't regret setting bombs" and "I feel we didn't do enough", and, when asked if he would "do it all again", as saying "I don't want to discount the possibility."
The interviewer also quoted some of Ayers' own criticism of the Weathermen in the foreword to the memoir, whereby Ayers reacts to having watched Emile de Antonio's 1976 documentary film about the Weathermen, Underground: "[Ayers] was 'embarrassed by the arrogance, the solipsism, the absolute certainty that we and we alone knew the way. The rigidity and the narcissism.' " "We weren't terrorists," Ayers told an interviewer for the Chicago Tribune in 2001. "The reason we weren't terrorists is because we did not commit random acts of terror against people. Terrorism was what was being practiced in the countryside of Vietnam by the United States."