Richard_J._Daley Richard Joseph Daley (May 15, 1902boss of Chicago and is considered by historians to be the "last of the big city bosses." He played a major role in the history of the Democratic Party, especially with his support of John F. Kennedy in 1960 and of Hubert Humphrey in 1968.Daley was Chicago's third mayor in a row from the working-class, heavily Irish American Bridgeport neighborhood on Chicago's South Side, and he lived there his entire life.