The City of Chicago rejected Boris Gudkovich’s request for a disabled parking permit and reserved spot outside his home. He sued, alleging a violation of the Americans with Disabilities Act. During discovery, the city insisted the deliberative-process privilege applied to 16 emails between two Department of Finance employees who discussed his application. The question for U.S. Magistrate Judge Jeffrey I. Cummings was whether this privilege applies when “the government’s decision-making process is central to the case …