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Answer:
DALEY
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Big name in Chicago politics
Windy City politician
Chicago mayor before Emanuel
Chicago political name
Chicago mayor
Big name in Chicago
Chicago name
Prominent Chicago politician
Longtime Chicago mayor
William ___, secretary of commerce under Clinton
Surname shared by Chicago's two longest-serving mayors
Sawyer's successor in Chicago
Richard J. of Chicago
Prominent U.S. mayor
Political name in Chicago
Mayor who died in 1976
Last of the big city bosses
Last name of father-and-son mayors of Chicago
Former boss in Cook Co., Ill.
Family name in Chicago politics
Emanuel's predecessor as mayor of Chicago
Either of two Chicago mayors
Diver Tom
Commerce secretary before Mineta
Chicago's Richard ___ Center
British diver Tom
Big name in Chi-town