As a trial and appellate court judge, Webb was  actively involved in the controversy over gay rights. Earlier in his career, he gave or upheld long prison sentences for consensual sex in several notable prosecutions under North Carolina's felony crime against nature law, two of which were upheld by the United States Supreme Court.
Webb, a judge on both trial and appellate courts, was deeply involved in the legal battles surrounding gay rights. During his earlier career, he presided over cases involving consensual sex, resulting in lengthy prison sentences for those convicted under North Carolina's "crime against nature" law, two of which were upheld by the Supreme Court.