Richard Joseph Daley (May 15, 1902 – December 20, 1976) served for 21 years as the mayor and undisputed Democratic boss of Chicago and is considered by historians to be the "last of the big city bosses." He played a major role in the history of the Democratic Party, especially with his support of John F. Kennedy in 1960 and of Hubert Humphrey in 1968.

Daley was Chicago's third mayor in a row from the working-class, heavily Irish American Bridgeport neighborhood on Chicago's South Side, where he lived his entire life.

Daley had two bases of power, serving as a Committeeman and Chairman of the Cook County Democratic Central Committee from 1953, and as mayor of Chicago from 1955. He used both positions until his death in 1976 to dominate party and civic affairs. Daley's Democratic political machine was often accused of corruption, but while many of Daley's subordinates were jailed, Daley was never formally charged with corruption.

He is remembered for doing much to avoid the declines that some other "rust belt" cities like Cleveland, Buffalo and Detroit experienced during the same period. He had a strong base of support in Chicago's Irish Catholic community, and he was treated by national politicians such as Lyndon B. Johnson as a preeminent Irish American, with special connections to the Kennedy family.

Daniel David "Dan" Rostenkowski (January 2, 1928 – August 11, 2010) was a United States Representative from Illinois, serving from 1959 to 1995. Raised in a blue-collar neighborhood on the Northwest Side of Chicago, Rostenkowski rose to become one of the most powerful legislators in Washington. He was a member of the Democratic Party. The son of an alderman and a product of the Cook County machine, Rostenkowski was for many years Democratic Committeeman of Chicago's 32nd Ward, retaining this position even while serving in Congress.

In Washington, he rose by virtue of seniority to the rank of Chairman of the House Ways and Means Committee in 1981, just as the Reagan Revolution marginalized many other Democratic politicians. As Chairman of Ways and Means, he played a critical role in formulating tax policy during the Republican administration of Ronald Reagan, including the Economic Recovery Tax Act of 1981, which cut income taxes by 25%, and the Tax Reform Act of 1986, which further cut taxes and reduced the number of brackets to only two. He was also involved in trade policy, as well as reforms of the welfare system, health care and Social Security programs

Harold Lee Washington (April 15, 1922 – November 25, 1987) was an American lawyer and politician who became the first African-American Mayor of Chicago, serving from 1983 until his death in 1987.

Harold Washington was born on April 15, 1922, to Roy and Bertha Washington. His father had been one of the first precinct captains in the city, a lawyer and a Methodist minister. His mother, Bertha, left a small farm near Centralia, Illinois, to make a fortune in Chicago as a singer. She married Roy soon after arriving in Chicago and had three children, one named Kevin and the other named Ramon Price (from a later marriage), former artist and chief curator of The DuSable Museum of African American History.

Washington grew up in the Bronzeville neighborhood of Chicago, at the time the epicenter of black culture in the city. He attended DuSable High School, then a new segregated high school, and was a member of the first graduating class. In a 1939 citywide track meet, Washington placed first in the 110 meter high hurdles event, and second in the 220 meter low hurdles event. Between his junior and senior year of high school, Washington dropped out, claiming that he no longer felt challenged by the classwork. He worked at a meat packing plant for a time before his father helped him get a job at the U.S. Treasury. There he met Dorothy Finch, whom he married soon after—Washington was 20, and Dorothy 17. Seven months later, the U.S. was drawn into World War II with the bombing of Pearl Harbor.

The Mayor of Chicago is the chief executive of Chicago, Illinois, the third largest city in the United States. He or she is charged with directing city departments and agencies, and with the advice and consent of the Chicago City Council, appoints department and agency leaders.

The Mayor appoints the Commissioner of the Chicago Fire Department and Superintendent of the Chicago Police Department. He or she is also responsible for appointing the heads of city departments, the largest of which are the Water Management Department (formed by the consolidation of the former Water Department and Sewer Department under Richard M. Daley) and the Streets & Sanitation Department. He or she additionally appoints members to the boards of several special purpose municipalities including the Chicago Park District, Chicago Public Library, Chicago Housing Authority, Chicago Transit Authority, the Metropolitan Pier and Exposition Authority, et al. Under Richard M. Daley, the Illinois legislature granted the mayor power to appoint the Chief Executive Officer of the Chicago Public Schools and subordinated the district under the mayor's authority; the district had long been an independent political field.

Leon Mathis Despres (February 2, 1908 - May 6, 2009) was an American author, attorney and politician. He was best known as a long-time alderman in Chicago, where he regularly disagreed with then-mayor Richard J. Daley, often engaging in loud arguments and debates on the assembly floor.

A native of Chicago, Despres received his undergraduate and law degrees in 1927 and 1929, respectively, from the University of Chicago, where he was elected to Phi Beta Kappa, before beginning a legal practice.

In April 1955, Despres was elected to the Chicago City Council from the city's Hyde Park neighborhood, as alderman of the 5th ward. Serving until 1975, Despres gained fame as an independent Democrat, consistently opposing the policies of Chicago Mayor Richard J. Daley. Frequently on the short end of 49-1 votes, Despres became known as the "liberal conscience of Chicago." Because of his strong advocacy of civil rights and open housing, Despres also became known as "the lone negro on the City Council," even though he was white and the council had six black alderman allied with the mayor.