[2] O'Connor is the son of a Deputy Commissioner of the Department of Streets and Sanitation, Bureau of Equipment Services, under Chicago Mayor Richard J.

Fresh from law school, O'Connor successfully sued the city for back pay for his father after Mayor Jane Byrne fired him.

During the tenure of Mayor Harold Washington, who was black, O'Connor, who is white, caucused with the mostly-white opposition block in City Council known as the "Vrdolyak 29".

[1] In his first term, a federal grand jury investigated O'Connor for providing, in late 1983 and again in late 1984, year-end jobs on the Education Committee staff for fifteen persons, including his mother-in-law, his brother-in-law, his sister-in-law, wives of two former members of his law firm, and the wife of a former staff aide.

[6] In May 2013, O'Connor suggested that the Catholic Church and other religious institutions and not for profit organizations should pay property taxes and be billed for water provided by the City of Chicago.

How about paying for the property you own.” O'Connor further suggested that the Catholic Church should not criticize the plan to bill it for water use, but ought to address its clerical abuse scandals.

Barbara sold more than $22 million worth of houses and condos in the 40th ward after the projects were enabled by Alderman O'Connor.