Chicago businessman James Weiss may not exactly be a household name, but he's spent his life running in the city's powerful political circles.The grandson of a former deputy city treasurer and friend of Mayor Richard Daley, Weiss married into the family of longtime Cook County Democratic boss Joseph Berrios, ran a political action committee with ties to then-House Speaker Michael Madigan, hooked up with Iranian-American businessman who calls himself the "Wolf of Rush Street" on a series of lucrative valet parking companies, and later, through connections with a fired Chicago cop and the help of a state legislator, got into the shady, unregulated world of sweepstakes gaming machines.
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