For years, John Ashcroft, as Missouri’s attorney general, relentlessly fought efforts by others in the community to forge a resolution to the problem of segregation in St. Louis schools. He strenuously resisted efforts to shape a voluntary desegregation plan, filing appeal after appeal, and earning scathing criticism from observers and leaders in the community. Ashcroft’s tactics were likened to the "massive resistance" employed by virulent segregationists during the early days of the civil rights movement. Many religious leaders, including the St. Louis Archbishop, united in opposition to Ashcroft’s rheteoric and tactics on desegregation. Newspapers and commentators around the state regularly and roundly denounced him. Perhaps the most stinging rebuke of all came from the federal court in ruling against Ashcroft’s attempts to block payment of plaintiffs’ attorneys’ fees in the case on the grounds that they were excessive. The judge wrote, "If it were not for the State of Missouri and its feckless appeals, perhaps none of us would be here today."
In 1982, Attorney General Ashcroft’s office represented the state in a criminal appeal brought by a convicted burglar and rapist. On appeal, the defendant, an African American, argued that certain prospective jurors, all white, should have been stricken from the jury because of their responses to a question asking "How many people here over the past two years . . . heard a black man referred to as something other than a negro? . . . A nigger, a coon, or some other name... How many people have not? . . . Have not referred to a member of the negro race, black man, by another name." On appeal, in a brief bearing Attorney General Ashcroft’s name and that of one Assistant Attorney General, the state correctly pointed out that the question asked of the prospective jurors was ambiguous, in that it combined a person’s both having "heard" or "used" racial slurs. However, the state’s brief did not stop there. Instead, it went on to assert: "Moreover, the mere use of another term for black or negro is not necessarily indicative of racial bias."
During the 1970s , women’s rights advocates were engaged in a nationwide effort to secure ratification of the proposed Equal Rights Amendment to the U.S. Constitution, which Congress had passed in 1972. In 1977, with the ratification deadline approaching, the National Organization for Women helped to organize a boycott to persuade organizations not to hold their conventions in those states, including Missouri, that had not ratified the ERA. In early 1978, Ashcroft, as the Attorney General of Missouri, brought a federal lawsuit on behalf of the state against N.O.W., claiming that the organization had violated a federal antitrust law prohibiting restraint of trade. Ashcroft’s unsuccessful lawsuit could have stifled NOW’s First Amendment rights.