For more than a quarter century, Shaw and his identical twin brother William were dominant political "kingmakers" of Chicago's far South Side and southern suburbs.
[11] Shaw and his brother learned politics from working in the 24th Ward Regular Democratic organization run by Arthur X. Elrod on the city's west side.
[5][10] The Shaw brothers both moved to the far South Side of the city, believing it to be the best location to establish an African American-led Democratic Party organization.
[15][16] In 1975, Shaw ran his first campaign for the Chicago City Council, unsuccessfully challenging incumbent 9th ward alderman Alexander Adduci.
[12] He received criticism from Black independents when he voted in favor of Byrne's redistricting map for the city's wards, which a federal court would subsequently rule as being unfair to African Americans and Latinos.
[12] A January 1981 article by F. Richard Ciccone of the Chicago Tribune described Shaw as "no stranger to city council controversy, though only a freshman alderman".
[20] Shaw and Wilson Frost both argued that eliminating the personnel code, and its testing requirements, would be beneficial to Black job applicants.
[2][9] In December 1986, Shaw and his brother held a press conference in which they alleged that people were being denied care by health maintenance organizations (HMOs) for life threatening conditions.
[7] In September 1987, Shaw and fellow alderman Allan Streeter introduced a bill to remove the image of a sailing ship from the 150-year old city seal, alleging that it represented "official government sanction of slavery".
[33] 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".
[22] After Harold Washington's death in office, Shaw joined Edward M. Burke in stopping Timothy C. Evans' bid to be appointed his mayoral successor.
[38] In 1988, Shaw was criticized for questioning witnesses at City Council hearings about their ethnic backgrounds, and was also accused of having made antisemitic remarks about "Washington Jews".
[32] During the mayoralty of Richard M. Daley, Shaw was a somewhat independent member of the council, giving criticism to the mayor and casting votes in opposition to his budgets.
[53] 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.
[38] On occasion, however, he did dissent in a number of cases where Berrios and the board's third member, Maureen Murphy, both voted to lower the tax rates on large properties in downtown Chicago.
[60] The Cook County state's attorney's office investigated accusations that Shaw had helped to arrange a property tax break for his brother (saving him as much as $1,219), but found no wrongdoing.
[62][63] In 2006, Shaw's brother William, then the mayor of Dolton, Illinois, appointed him to be city's first inspector general, a newly created position that paid $70,000 annually.
In 2005, federal investigators discovered a practice that existed in Dolton and a number of other Chicago suburbs where politically connected citizens were allowed to carry guns and mimics of police badges.
[38] For more than a quarter century, Shaw and his brother William were dominant political "kingmakers" of Chicago's far South Side and southern suburbs.
[5][15][16][17][69][70] Their tide first began to change when Jesse Jackson Jr. won election to U.S. congress in 1996, defeating the Shaw brothers-backed candidate Emil Jones in the Democratic primary.
[17] In 2000, Jackson Jr. backed David E. Miller in his successful state representative Democratic primary race against Shaw-backed candidate Willis Harris.
[17] In 2002, Jackson Jr. encouraged James Meeks to make his successful general election challenge to William Shaw for state senate.
[55] In 2004, Jackson backed Larry Rogers Jr.'s successful primary challenge against Shaw for Cook County Board of Review.
[76][77] After Shaw's death, the Chicago Crusader credited him and his brother's political organization with successfully pushing the Illinois State Legislature to establish new Cook County Circuit Court and Illinois Appellate Court sub-circuits located in African American city wards, which the Chicago Crusader wrote had the impact of enabling more than 60 African American individuals to become judges.
[79] In October 2004, Shaw announced that he would be challenging incumbent village president (mayor) Don DeGraff in the April 2005 South Holland, Illinois, election.
Shaw claimed that DeGraff was a supporter of heavily conservative politician Alan Keyes, who had been the Republican Party nominee who ran against Democrat Barack Obama in the 2004 United States Senate election in Illinois.
[4] In 2006, Shaw ran for the Democratic nomination for the 29th district seat in the Illinois House of Representatives, seeking to unseat incumbent David E.
[31][27][99] He also voiced concern of the city's ability to fund pension programs for municipal employees,[27][99] criticizing cutting benefits for retired workers.
[9] He described his campaign strategy as aiming to bring together a coalition of African Americans, Latinos, and others displeased with the policies of the incumbent mayor.
[16] During his candidacy, an early July 2014 poll taken by We Ask America showed that, in a head-to-head matchup, incumbent mayor Rahm Emanuel led him 47.7% to 29.6%, with 22.8% of voters being undecided.