Ed Siskel speaks during a news conference at the Dirksen Federal Courthouse, Monday, Aug. 7, 2017, in Chicago. (AP Photo / G-Jun Yam, File)

Under the Obama administration, Ed Siskel oversaw the White House legal response to congressional oversight and the rollout of the Affordable Care Act. Siskel, a Chicago native and the nephew of movie critic Gene Siskel, served for two years as the top lawyer in Chicago.

Attorneys for the city of Chicago on Monday hoped to convince a federal judge that plans by the U.S. Department of Justice to withhold federal grant money over immigration enforcement is unconstitutional.

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Illinois Attorney General Lisa Madigan sues for federal oversight of Chicago police reform—with the city’s blessing. We discuss the lawsuit.