Jackson was born on September 1, 1870, in Malta, Illinois, but while still an infant moved with his parents to Chicago, where he spent the remainder of his life. His father, William Jackson, was a native of St. Catherines, Ontario, Canada; his mother, Sarah (Cooper) Jackson, of Hagerstown, Maryland. The family was poor, and at the age of nine Robert began work after school hours as a bootblack and newsboy.
Jackson left school in 1883 at the end of the eighth grade.
In 1888, passing a civil service examination with a high score, Jackson entered the postal service, where in nine years he advanced to the position of assistant superintendent of a Chicago postal station. During this period he also entered into a number of business ventures, and became active in local military, fraternal, and political affairs. He joined the Illinois national guard in 1888 as a drummer boy, and during the Spanish-American War was commissioned a major. His principal business enterprise was a printing company which supplied constitutions and by-laws to black fraternal orders; its prosperity enabled Jackson to leave the postal service in 1909. He was a member of nearly every black lodge and civic club in the city. Jackson became best known, however, as a political leader. "The Major, " as he was commonly called, entered politics in the 1890's as a protégé of Edward Wright, Chicago's first successful Negro machine politician, and Jackson's entire political career was closely linked with the rise and fall of Wright's Republican organization, which dominated Negro politics in the city from the turn of the century until the 1930's. After 1915, Wright and Jackson were firmly allied with Mayor William Hale Thompson, the flamboyant political boss who virtually ran Chicago politics for a decade and a half. Jackson was elected to the state legislature in 1912 and to the city council in 1918, at a time when thousands of Southern black migrants were crowding into Chicago in search of jobs and a greater measure of human dignity. Conditioned by their Southern experience to support the "party of Lincoln, " the migrants formed the core of Jackson's electoral base. As legislator and alderman, Jackson attempted to represent the interests of these constituents while at the same time giving vital political support to Wright and Thompson. During his three terms in the legislature (1913-1919), he was instrumental in killing an anti-intermarriage bill and a bill that would have reduced employment opportunities for Negroes on the railroads. He also fought to curb the distribution of racist films and literature and secured a $50, 000 appropriation for an Emancipation Golden Jubilee in 1913. On the city council, representing the Second Ward (later the Third Ward), Jackson sponsored a pure milk ordinance, an ordinance forbidding Ku Klux Klan parades in the city, and appropriations for schools, athletic fields, playgrounds, and parks in the black community. For a time, he served as Thompson's floor leader. In his twenty-one years on the city council, Jackson weathered numerous electoral challenges from both within and outside the Thompson-Wright organization. In the 1930's, however, his political fortunes ebbed as the Republican Thompson machine was replaced by the Democratic Kelly-Nash machine and the majority of Negro voters, hit hard by the depression, shifted their allegiance to the Democratic party and Roosevelt's New Deal. Jackson attempted to make his peace with the new political order and for a while had the support of the Democratic leadership. But unlike his fellow black councilman William Dawson, he never became a Democrat, and he was defeated by a Democratic challenger in 1939. Jackson died on June 12, 1942, of cerebral apoplexy at the Provident Hospital in Chicago, and was buried in Chicago's Oakwood Cemetery.
Jackson belonged to a generation of black politicians who attempted to build political organizations comparable to the finely tuned machines of the white immigrant political bosses. Faced with limited options, he attempted, within the framework of his own value system, to alleviate, at least, the hardships of ghetto life.
Jackson's primary concerns were patronage jobs and police protection for his constituents and practical improvements for the community he represented. He never questioned the political system within which he operated or thought in terms of long-range goals. His own rise from poverty to affluence and prestige, which he never tired of recalling, indicated to him that blacks could make the system work for them, and he sharply criticized those who failed to work hard, save money, and care for property. Reform-minded contemporaries frequently pointed to the limitations of this approach and questioned the value of the favors which Jackson and his colleagues won for their people. Clearly, Jackson's politics did little to meet the deep-seated problems of the urban black ghetto - the problems of poverty, discrimination, and alienation. Yet he saw no viable alternatives: the reform movements of his day usually ignored black people, and radical programs seemed to him utopian and impractical.
Jackson was survived by his wife, Hattie Ball Lewis, and their one son, George. Robert R.
