Turn of the century El Paso had it all: wealth, poverty, and an infamous red-light district. After the city shuttered the vice district in 1917, many of El Paso’s men and women continued to champion regulated prostitution to curtail streetwalkers and call girls who solicited in the business district and residential neighborhoods. Many of El Paso’s men and women considered prostitution prohibition folly, thus they proposed practical measures which allowed for fines and licensing fees to be assessed to feed the city coffers while imposing medical exams on sex workers to curb the spread of sexually transmitted diseases. Residents supported a zone of tolerance where police allowed prostitutes to practice their trade without repercussion. This study presents the factors which led some working-class women to prostitution, explores the middle and upper-class men and women who called for regulated prostitution in contradiction to a nation teaming with social hygienists and uncovers the work of police matrons tasked with investigating suspected sex workers. Using the logbook of matron Victoria Mendez as evidence, the fanning out of prostitutes becomes clear. Whereas much research can be found on those who demanded moral policing, this work highlights a city of Texans who concluded that tactic a fool’s errand.