Lurker
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When the city is the second largest employer in the city, there's a large concentration of public housing, and a high concentration of other people or organizations utterly dependent on the public dole, there's no way an incumbent mayor, unless threatening to cut off the gravy, is going to be voted out. Too many people are dependent on the king staying in power and distributing the goodies. The affluent minority paying for the whole patronage scheme is too small to unseat the king and still not quite irked enough to vote with their feet. Of course if the universities, medical/research centers, and corporate HQs were to leave, then the whole scheme would fall apart rather rapidly. As there would no longer be any reason for the affluent to stay, and it's hard to run a patronage kingdom without someone to extort the capital to run one from. Chicago is actually further down the road of this downfall than Boston at this point. Hence why King Daley decided to abdicate the throne.