I keep returning to David Moberg's 1989 piece about the big money players behind Richard M. Daley ("not a machine of pinky rings and tavern owners, but one of alligator briefcases and law-firm partners") when thinking about how power is wielded in Chicago—the rise of business money against neighborhood, cultural/ethnic, and labor affinities—and how an election might be won now.
Some of the evolution can be chalked up to the increasing importance of corporate money in politics generally, and specifically in a city that's grown more focused on its white-collar business and tourist central district in the past three or four decades. But reading Wendt and Kogan's Lords of the Levee (specifically a sexily retitled 1971 edition, Bosses in Lusty Chicago), Paul Douglas makes an interesting point in his introduction about Chicago and the American metropolis that I hadn't considered. It's worth quoting at length:
Fortunately the old ward bosses of the type of Martin Lomasney of Boston, Big and Little Tim Sullivan and "The McManus" of New York, and Iz Durham and Ed Vare of Philadelphia, are fast fading from the political scene. They have been largely displaced by a number of changes of which the most important have been, first, the development of social security and welfare legislation which provide protection in a relatively self-respecting manner against some of the terrible risks of industrial life—industrial accidents, unemployment, indigent old age, and many forms of poverty. These have displaced the gratuities of the ward boss and have lessened the dependence which the poor and the unfortunate used to feel toward those who at once exploited and protected them. A second factor has been the great decrease in the immigrant tide which used to run at the rate of a million persons a year. This huge influx created cultural enclaves within our cities which in turn helped to raise to power the ethnic ward bosses like Cermak, Stanley Kunz, and Moe Rosenberg of Chicago. The new migration cityward of Negroes and Puerto Ricans has created somewhat analogous groups, to be sure, but not to the same degree. A third factor that has diminished the power of the ward boss has been the great reduction in poverty and the improvement of the material condition of the people. There are still a great many poor people in the country. Probably a sixth can be fairly classified as being poor, and a fourth as poor or near-poor. But the proportion is not as high as it was, and city folk, even with the Negro migration, are not as dependent as they were. Those who can stand on their own feet do not need the protection of the ward leader as much as did their parents and grandparents.