For many years, Shaw and his twin brother Robert were dominant political "kingmakers" of Chicago's far South Side and southern suburbs.

[10] By the early 1970s, the two brothers had moved to the far South Side of Chicago,[6][10] believing it to be the best location to establish an African American-led Democratic Party organization.

[5] In 1984, Shaw and his brother became outspoken proponents for the passage of legislation make black history required curriculum in Illinois public schools.

[21] After his 2002 loss for reelection to the state senate, lame duck governor George Ryan (a Republican) named Shaw to the position of Small Business Utility Advocate for a term that would have started March 1, 2003.

Ultimately, in February 2003, Governor Rod Blagojevich (a Democrat) chose not to put anyone forward for the position as a cost saving measure.

After Shaw's death, Ronnie Lewis was named by the village board of trustees (city council) to serve as interim mayor.

[30] In 2005, the Village of Dolton filed a lawsuit against a taser manufacturer alleging that it had not sufficiently tested a product it marketed as being nonlethal.

[31] In 2006, Shaw appointed his brother Robert to the newly created position of Dolton inspector general, which paid $70,000 annually.

[36] In 2010, a lawsuit against the Village of Dolton alleged that, in 2007, Shaw had rigged the results of a police sergeant's exam in order to favor two officers for promotion.

[37] For more than a quarter century, Shaw and his brother Robert were dominant political "kingmakers" of Chicago's far South Side and southern suburbs.

[15][11][38] 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.

[15] In 2000, Jackson Jr. backed David E. Miller in his successful state representative Democratic primary race against Shaw-backed candidate Willis Harris.

[39] In 2004, Jackson backed Larry Rogers Jr.'s successful primary challenge against Robert Shaw for Cook County Board of Review.

By 2006, the Shaw brothers were using a public-access television program in Dolton to regularly assail Jesse Jackson Jr. and other political foes.

Shaw and Zuccarelli remained friendly, which led to some speculation that they had both run in order to split the vote away from Giglio so that one of them would beat him.

[51][52] In 2022, after Robert Shaw's death, The Chicago Crusader credited the Shaw brothers' 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.