A Republican, De Priest had resigned in scandal after being indicted of accepting a bribe from a gambling establishment, of which he would eventually be acquitted. His main opponent in the race was William Rudolph Cowan, an African-American real-estate broker who had the backing of reformers. De Priest attempted to retake his seat in 1918 but narrowly fell in the Republican primary to Major Robert R. Jackson, who would go on to win the general election. Throughout the 1920s he was a prominent ally of mayor
William Hale Thompson and served as his floor leader in the Council. and was immensely popular with the city's African-American community. 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", 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. In 1923 Chicago's wards were increased from 35 to 50, while the number of aldermen per ward was decreased from two to one. Jackson was redistricted to the new 3rd ward, while Anderson kept his 2nd ward seat. In 1923 he was implicated in collecting more than $15,000 in protection money in the span of twenty months from a
black and tan resort. 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. He still contested the election and won with a majority of 1,037 votes, defeating eight opponents to avoid a runoff. Democrat
William Emmett Dever was elected mayor in 1923; Anderson opposed his 1924 budget, claiming that his proposed reclassification of hundreds of civil service jobs was meant to eliminate the current civil service workers. In that same year he served as a delegate to the
1924 Republican National Convention. Upon Thompson's return to the mayoral office following the
1927 election rumor had it that Anderson was likely to receive the "prize plum" of the chairmanship of the Council's finance committee, but Council Democrats worked to keep him off the committee and it seemed likely that the position would go instead to 30th ward alderman John Clark. In the
1931 election he initially had five opponents, but rulings by the board of election commissioners invalidated the nominating petitions for all of them, leaving him unopposed. In that year's
mayoral election he abandoned Thompson, whose popularity had plummeted due to crime and the Great Depression and who would be decisively defeated in the contest by Democrat
Anton Cermak. Nevertheless, the 2nd ward was one of five in the city that voted Thompson, Later in the year he considered running for the
United States House of Representatives against De Priest, then the only African-American in Congress. 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. In 1936 he ran for the Republican nomination for
Illinois's 1st congressional district, falling to De Priest. ==Personal life==