 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.In 1974, as a trial court judge in Wilson Count, Judge Webb presided over the trial of Eugene Enslin for crime against nature and sentenced him to a year in prison.Enslin's appeal to the U.S. Supreme Court was denied in 1975 at the same time that it upheld Virginia's sodomy law in Doe v. Commonwealth's Attorney.