In 1965, Ayers was part of a group who were protesting at a restaurant in Ann Arbor, Michigan. The restaurant would not serve African Americans. Ayers' first arrest came when he took part in a sit-in at a local draft board. He sat in jail for ten days. Shortly after his arrest, he landed his first teaching job at the Children's Community School. This small preschool was run from a local church basement. The preschool was part of a larger movement across the United States called the "free school movement". Schools that were part of this movement had no grades or report cards. Instead, they tried to work on getting students to cooperate with each other and work together instead of competing. The teachers allowed the students to call them by their first names. After teaching for only a few months, at the age of 21, Ayers became the head of the school. There he also met Diana Oughton, who would be his girlfriend until her death in an explosion in 1970.
Ayers became part of the New Left and the Students for a Democratic Society (SDS) in the early 1960s. In 1968 and 1969, Ayers became well known as a head of the SDS. He was head of a smaller SDS group called the "Jesse James Gang". Ayers made important changes to Weatherman beliefs about being militant (ready to fight for the cause). The group that Ayers headed in Detroit, Michigan became one of the first groups that would turn into the Weathermen. Before the June 1969 SDS convention, Ayers became an important head of the group. This came about due to a split in the group.
In June 1969, the Weathermen took over the SDS at its convention. Ayers was made Education Secretary. Later in 1969, Ayers helped to place a bomb at a statue that was made to honor policemen that were killed. The bomb blast broke almost 100 windows and blew parts of the statue onto a nearby street. (The statue was rebuilt and unveiled on May 4, 1970, and blown up again by other Weathermen on October 6, 1970. While they were putting it back together, the city put a 24-hour guard around it to stop another attack. In January 1972, it was moved to Chicago Police headquarters. Ayers was also part of the "Days of Rage" riot that took place in Chicago in 1969. He was also a part of the "War Council" meeting that happened in Flint, Michigan. Two big decisions came from the "War Council". The first was to start a violent, armed resistance (using bombs, and robberies) against the government. The second was to start underground (secret) groups in important cities around the country. An FBI informant named Larry Grathwohl, who pretended to be a Weatherman in 1969, said that "Ayers, along with Bernardine Dohrn, probably had the most authority within the Weatherman".
In 1970, Weatherman members Ted Gold, Terry Robbins, and Diana Oughton were killed when a bomb they were building blew up. This was called the Greenwich Village town house explosion. Ayers and several other Weathermen were able to avoid being caught following this explosion. Ayers was not facing charges at this time, but the federal government later brought charges against him. Ayers was part of the bombings of New York City Police Department headquarters in 1970, the United States Capitol building in 1971, and the Pentagon in 1972. Ayers wrote, in 2001, that: Although the bomb that rocked the Pentagon was itsy-bitsy - weighing close to two pounds - it caused 'tens of thousands of dollars' of damage. The operation cost under $500, and no one was killed or even hurt.
Some new reports have said that Ayers, Dohrn, or the Weatherman took part in the 1970 San Francisco Police Department bombing. However, neither Ayers, nor anyone else has ever been charged with this crime.
In 1973, it was discovered that the FBI were focusing on the Weatherman as well as the New Left. This was part of several secret, and sometimes illegal FBI projects called COINTEL. Because the FBI agents had broken the law, the government asked that all weapons and bomb charges be dropped against the Weather Underground. This included charges against Ayers.
However, there were still state charges against Dohrn. Dohrn did not want to turn herself in to the police. "He was sweet and patient, as he always is, to let me come to my senses on my own", she later said of Ayers. She finally turned herself in, in 1980. She was fined $1,500 and given three years probation.
In 1973 Ayers helped write the book "Prairie Fire" with others who were part of the Weather Underground. They dedicated the book to almost 200 people, including Harriet Tubman, John Brown, 'All Who Continue to Fight', 'All Political Prisoners in the U.S.', and Sirhan Sirhan, who was convicted of killing Robert F. Kennedy.
In 2001, Ayers wrote "Fugitive Days: A Memoir". He said "Fugitive Days" tried to answer the questions of Kathy Boudin's son and his statement 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 (who was also a member of the SDS) said that Ayers' memories were wrong. Ayers, in the beginning of his book, says that it was written as his personal memories and was not a research project.
"Chicago Magazine" said that "just before the September 11 attacks", Richard Elrond, who was hurt in the "Days of Rage", was given an apology from Ayers and Dohrn. "[T]hey were remorseful," Elrod says. "They said, 'We're sorry that things turned out this way.'" Ayers gave a lot of interviews before his book was published. In these interviews he defended his history of radical words and actions. Some of the articles were written before the September 11 attacks and appeared right after. Many comments were made by the media comparing the statements that Ayers was making about his past just as a terrorist incident shocked the public.
A lot of the controversy about Ayers in the years since 2000 comes from an interview that he gave to "The New York Times". The reporter quoted him as saying "I don't regret setting bombs" and "I feel we didn't do enough". When asked if he would "do it all again," he said "I don't want to discount the possibility." Ayers questioned the interviewer's way of describing him in a "Letter to the Editor" on September 15 2001. In his letter, Ayers wrote: "This is not a question of being misunderstood or 'taken out of context', but of deliberate distortion." In the following years, Ayers has said that what he meant by saying that he had "no regrets" and "we didn't do enough" he was talking about their efforts to stop the US from fighting in the Vietnam War. He said these efforts were ". . . inadequate [as] the war dragged on for a decade." Ayers has repeatedly said that the two statements did not mean that he wished they had set more bombs.
Ayers was asked in a 2004 interview, "How do you feel about what you did? Would you do it again under similar circumstances?" He said: "I've thought about this a lot. Being almost 60, it's impossible to not have lots and lots of regrets about lots and lots of things, but the question of did we do something that was horrendous, awful? ... I don't think so. I think what we did was to respond to a situation that was unconscionable." On September 9, 2008, journalist Jake Tapper talked about the comic strip in Ayers' blog, where he explained the soundbite: "The one thing I don't regret is opposing the war in Vietnam with every ounce of my being... When I say, 'We didn't do enough,' a lot of people rush to think, 'That must mean, "We didn't bomb enough shit."' But that's not the point at all. It's not a tactical statement, it's an obvious political and ethical statement. In this context, 'we' means 'everyone.'"
In 2008, Ayers said this about his actions: