Born on April 17, 1870, in Petersburg, Virginia,[2] Anderson moved to Washington, D.C., in 1889 to work in journalism as an exchange reader,[3] and journalist.

[10] De Priest attempted to retake his seat in 1918 but narrowly fell in the Republican primary to Major Robert R. Jackson,[13][a] who would go on to win the general election.

[6] "Big Bill" Thompson had previously been alderman of the 2nd ward from 1900 to 1902[14] and was immensely popular with the city's African-American community.

[15] In 1921, when R. E. Parker of the Chicago Advocate confronted Thompson with the problems of 20,000 unemployed African-Americans and charged that the 2nd ward was full of graft and corruption, Anderson defended the mayor, calling Parker a "trouble maker among his own people",[16] denying allegations of racism in Thompson's layoff practices, and responding to the charges of graft thus: If he has the proof why doesn't he take it to the grand jury?

[17] Also in 1922 Anderson served on a committee looking into the Ku Klux Klan's alleged activities in the City's affairs, he and two other aldermen announced to the press that they had received death threats.

[19] In light of a related grand jury investigation, an illness, and the fact that Thompson declined to seek re-election that year, it was rumored that he would step down as alderman as well.

[26] In that year's mayoral election he abandoned Thompson,[27] whose popularity had plummeted due to crime and the Great Depression and who would be decisively defeated in the contest by Democrat Anton Cermak.

[28] Nevertheless, the 2nd ward was one of five in the city that voted Thompson,[28] and having campaigned expressly against Anderson Cermak removed him from the finance committee.

[30] The Chicago Review, despite its dislike for De Priest, suggested that such a course of action was ill-advised, a conclusion also reached by The New York Age.