Before stepping down in 1987, Oberman worked under four mayoral administrations, three of which he openly criticized.
But in the mid-1980s, he often voted with then-Mayor Harold Washington, whom he said did a "spectacular job of reforming the city." Oberman also unsuccessfully ran for Illinois attorney general twice, in 1986 and 1994. On a third occasion, in 1982, he campaigned for the office but never filed his candidacy.
Along with serving as first general counsel for the Illinois Racing Board, Oberman has chaired the city's Committee on Public Records and Information and recently sat on Emanuel's Midway Airport Advisory Panel. He also helped file a friend-of-the-court brief on behalf of Emanuel's campaign during the controversy over whether Emanuel met Chicago's residency requirements to run for mayor.
Last year, he wrote an opinion piece in the Tribune supporting what he said was transparency in Emanuel's administration. Despite that piece, Oberman said he's not in Emanuel's camp but feels the mayor has done a good job cleaning up City Hall.
Oberman said he plans to decline the $15,000 stipend that comes with the Metra position. He also said he spent the weekend studying the Metra budget and is ready for the assignment.
Metra riders "should feel comfortable knowing I'll be working for them," he said.