44. Matt Hynes
Son of former Illinois Senate president Tom and brother of former comptroller Dan, Hynes had the connections to land the job of Rahm’s campaign adviser and, after that, chief lobbyist. All things political inside City Hall—heck, that’s practically everything—go through his office. Already he has compiled an impressive list of victories: a Chicago casino, longer school days, and much of what the mayor has wanted in the City Council.
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Photograph: Brooke Collins