When President Bill Clinton had a rare opportunity in 1995 for a Democratic president to fill a vacancy on the federal appeals court based in Chicago, a bastion of conservative thinking, he received an unusually strong recommendation from Senator Paul Simon.

Mr. Simon, an outspoken liberal from Illinois who died in 2003, told the president the new judge should be a reliable progressive who would be cerebral enough to go up against the court’s two formidable conservatives, Judges Richard A. Posner and Frank H. Easterbrook. He said it should be Prof. Diane P. Wood of the University of Chicago law school.

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