For more than a quarter century, Shaw and his brother Robert were dominant political "kingmakers" of Chicago's far South Side and southern suburbs. They built a
political machine that garnered the support of the African American electorate in the area. Over the years, their main rivals for influence there was the Jackson family, Jesse Jackson and Jesse Jackson Jr. Their influence dissipated greatly in the late 1990s and the early 2000s, with Jesse Jackson Jr. largely beating them out to become the new kingmaker at the time. 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. In 2004, Jackson backed Larry Rogers Jr.'s successful primary challenge against Robert Shaw for
Cook County Board of Review. Also in 2004, the Shaw brothers denied involvement with two challengers running against Jackson for congress, who each filed challenges to the younger Jackson's petition signatures (which, if successful, would have seen Jackson removed from the ballot in the Democratic primary). The two challengers to Jackson worked for Dolton (where Shaw was mayor), and used the village's attorney as their lawyer. As mayor, Shaw utilized the trappings of his office to attack political enemies. By 2006, the Shaw brothers were using a
public-access television program in Dolton to regularly assail Jesse Jackson Jr. and other political foes. From 1988 until 1996, Shaw served as Democratic
committeeman for Chicago's 9th ward, an elected Democratic Party position. In 1996, Shaw's brother, Robert, succeeded him as 9th ward committeeman. However, he would only hold the office for a single term, being unseated in 2000 by Anthony Beale, an ally of Jesse Jackson Jr. In the years that the Shaw brothers ran the 9th Ward Regular Democratic Organization, they and their campaign volunteers helped deliver strong voter support for campaigns of African American politicians such as Mayor
Harold Washington and Illinois State Senator
Emil Jones, and the
1992 U.S. Senate campaign of
Carol Moseley Braun. They also helped mobilize support in the area for the
2004 U.S. Senate campaign of
Barack Obama. In 2002, Shaw ran for Democratic committeeman for
Thornton Township, challenging
Frank Giglio (who had served as committeeman for 29 years). Also challenging Giglio was
Frank Zuccarelli, the superintendent of the township. At the time, the township's Democratic Party had fractured into three camps: those loyal to Shaw, those loyal to Giglio, and those loyal to Zuccarelli. 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. They both denied that that was the case. Zuccarelli won, while Shaw placed second. Among the individuals that got their starts in the political organization run by the Shaw brothers was
Mose Jefferson. 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. ==Personal and death==