After law school, Reggie clerked for Judge Robert Arthur Sprecher at the U.S. Court of Appeals for the Seventh Circuit in Chicago. As an attorney, she specialized in bank law. She met her first husband, Grier C. Raclin, a telecommunications attorney (who later became a senior executive at Charter Communications in St. Louis, Missouri), when they clerked together at the Everett McKinley Dirksen Federal Courthouse. Their 1981 church wedding was in Crowley and "feted four hundred guests with a week's worth of parties."