In a series of interviews Tony Bowe conducted with Bill Bowe about their extended families, Tony in this session asks Bill how he became interested in becoming active in Chicago’s anti-machine mayoral politics of the 1970s. The discussion touches on family influences and serving in the Pentagon during the racial disturbances and antiwar protests between 1968 and 1971. Bill explains being asked in the mid-70s to take a leave of absence from his law firm to work in a Chicago mayoral campaign aimed at the defeat the political machine of Mayor Richard J. Daley. Bill concludes by talking with Tony about the political apprenticeship of Jane Byrne and the defeat of the Daley machine with her election as Chicago’s Mayor in 1979. Bill also discusses with Tony how she undermined her bid for reelection and went down to defeat in 1983 by Harold Washington, Chicago’ first Black mayor. Bill closes with some personal observations regarding Mayor Washington.