Shaw served two tenures as the alderman from Chicago's ninth ward. In 1975, Shaw ran his first campaign for the Chicago City Council, unsuccessfully challenging incumbent 9th ward alderman
Alexander Adduci. Shaw used racially charged rhetoric during the campaign. Shaw rose to prominence as a main
African American community ally of Mayor
Jane Byrne. He would tell the media, "I asked my friends, Ed Vrdolyak and
Fred Roti to help me out, and they did". In its
obituary for Shaw, the
Chicago Crusader credited him with supporting hundreds of ordinances in his two stints as an alderman that had the impact of providing more opportunities for black-owned businesses to do business with the city government. In 1982, Shaw voted against the
handgun ban ordinance championed by mayor Byrne. The legislation passed without his support. In 1982, Shaw also introduced an ordinance that would have increased the salary of aldermen from $27,600 to $46,350. After this, Mayor Byrne publicly declared she would veto any pay raise for Chicago aldermen. Shaw lost reelection to Perry H. Hutchison in 1983. Shaw's loss was attributed to his choice to endorse incumbent mayor Byrne over
Harold Washington in the Democratic primary for the
coinciding mayoral election. Hutchison, however, had supported Washington against Byrne in the mayoral primary.
Interregnum between tenures In 1984, Shaw and his brother took up the cause of calling for legislation to be passed to require black history to be taught in
public schools.
Second tenure (1987–1998) During the Washington and Sawyer mayoralties (1987–1989) In 1987, Shaw defeated Hutchison to regain his old seat on the Chicago City Council. Hutchison had been indicted for taking bribes in a federal
sting operation ahead of the election. In 1990,
John Kass of the
Chicago Tribune noted that Shaw had a penchant for basking in the media attention he received, despite the media largely regarding him as clownish. City documents had once described the high-masted sailing ship on the seal as, "emblematic of the approach of white man's civilization and commerce". Shaw declared, "The ship represents
institutionalized racism in this country." Shaw also called for a more thorough investigation into Washington's cause of death. Shaw was a chief backer of Sawyer during his mayoralty. Shaw had a tendency to make racially inflammatory statements. In 1988, Shaw also opposed a measure that would aim to stop the use of racial, ethnic, and sexual insults at committee hearings. He argued that it would infringe on the right of the council to, "protect the public interest." That same year, he also told the
Chicago Defender, "A white should not be mayor. When they were mayor, they did not treat blacks and other minorities fairly. They do not know how to be fair." His 1991 reelection saw him defeat
Chicago Transit Authority bus driver Johnny J. O'Neal by a mere 37 votes. O'Neal would subsequently, in 1993, attempt to have the legitimacy of the vote count reinvestigated through litigation. In 1989, Shaw opposed legislation championed by Daley to create a watchdog to oversee all of city government. The ordinance later passed, but with revisions that made aldermen exempt from the new inspector general's oversight. In 1990, Shaw proposed an ordinance to ban an
AIDS awareness advertisement campaign that had seen posters placed on city transit that included same-sex couples kissing, claiming that the posters were, "promoting a lifestyle, which I object to." In January 1993 Shaw, joined by
Dorothy Tillman, offered half-serious criticisms of former
Chicago Bears coach
Mike Ditka after Edward M. Burke proposed naming the 7th anniversary of the Bears'
Super Bowl XX victory "Mike Ditka Day" in Chicago. In 1993, Shaw opposed Daley's nomination of Thomas Scorza to be appointed
Chicago city clerk. Shaw opposed him due to testimony about improprieties in Scorza's office during his tenure as assistant U.S. Attorney. Shaw raised further allegations against Scorza, without providing any evidence publicly. In 1996, as part of
Operation Silver Shovel, the U.S. attorney's office
subpoenaed financial records from Shaw's campaign and ward funds, as well as telephone records. Before this, federal agents had unsuccessfully sought to interview Shaw. After resigning to serve on the Cook County Board of Review, he backed the candidacy of his son Herbert Shaw in the 1999 election to succeed him. However,
Anthony Beale, a political unknown backed by
Jesse Jackson Jr. and
James Meeks, defeated him in an
upset. == Cook County Board of Review ==