Daley was Chicago's third mayor in a row from the Bridgeport neighborhood. He served in that position longer than any other person. According to Chicago folksinger Steve Goodman, no man "could inspire more love, more hate." Known to the world as a Democrat, Daley's first elected position was as a Republican member of the Illinois legislature. When Republican David Shanahan died, Daley switched parties long enough to be elected to serve out his term and, immediately after the election, returned to the Democratic party. Daley suffered his only political defeat in 1946 when he lost a bid to become Cook County sheriff.
First elected in 1955, he served six terms as mayor, dying in office in 1976. Known for party politics, Daley was the prototypical "machine" politician, and his political machine has been considered by some to have been instrumental in helping to electing John F. Kennedy in 1960. Although the boss of a machine, Daley was not inaccessible, meeting each morning in a news conference, taking all questions, if not answering all of them.
Daley had limited opposition among the 50 aldermen of the Chicago City Council. Except for three Republicans from the prosperous wards on northwest side of the city and one independent Democrat representing the ward around the University of Chicago, all the aldermen voted his way consistently.
It was often alleged that his administration used questionable tactics to acquire votes, with the ironic phrase "vote early and vote often" frequently used to describe to his method of delivering votes. Any Democratic vote fraud in Cook County was easily matched statewide by Republican practices downstate, which included voting by telephone, and bulk voting by political leaders.
In fact, the main method used by Daley was the precinct captain, who marshalled and delivered votes on a neighborhood basis. Many of these precinct captains held patronage jobs with the city, mostly minor posts at low pay. Each ward had a ward leader in charge of the precinct captains. Some of these were corrupt. A few wards were tied to the local mafia or crime syndicate, but Daley's own ward was clean and his personal honesty was never questioned successfully.
Major construction during his terms in office resulted in O'Hare International Airport, the Sears Tower, McCormick Place and other Chicago landmarks. O'Hare was a particular point of pride with Daley and his staff regularly devised occasions to celebrate its "opening".
Nineteen sixty-eight was a bad year for Daley, between his order to shoot-to-kill rioters in the aftermath of Martin Luther King, Jr's assassination and the riots which occurred during the 1968 Democratic National Convention in Chicago. At the time, many Chicagoans supported Daley's actions during the DNC; however, a federal commission investigating the events later described them as a "police riot", blaming Daley for inciting the police to commit violence. One of Daley's most memorable malapropisms was uttered in 1968: "Gentlemen, get the thing straight, once and for all: the policeman isn't there to create disorder, the policeman is there to preserve disorder."
Daley was known for his tangled tongue. He often said he was exhilarating a program, rather than accelerating it, and called a bicycle built for two a tantrum bicycle, for instance. Reporters gathered after his press conferences to work out just what it was that he had said.
At his death in 1976, the public's perception of Daley was the image painted by Mike Royko in Boss—corrupt, racist, cruel, brutish. In light of the tarnishing of liberalism and New York City's fiscal crisis, Daley's reputation has risen considerably, as has the reputation of the political machine in general. Daley's ways may not have been democratic, but he got things done for Chicago which a non-boss would have been unable to do.
The definitive biography of Daley is American Pharaoh, by Adam Cohen and Elizabeth Taylor.