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A major factor in the overall enrollment decline in elementary and secondary Catholic schools during the past 50 years has been the migration of families from urban parish schools to suburban public education. Nearly 13,000 Catholic schools operated in the early 1960s. By 2016 that number was down to roughly 6,400. The enrollment decline coincided with rising expenses at Catholic schools. Schools in the Chicago-based Cristo Rey Network serve low-income families in urban areas, are doing what many thought impossible. Rather than losing students they are adding them. In its unique model, students receive a college-preparatory education and participate in a work-study program in which they learn employable skills and earn money to help pay for their tuition. Since the first Cristo Rey school was founded in Chicago in 1996, 31 others have opened in 21 states and the District of Columbia, including in Boston and Lawrence, MA, with plans to add eight more by 2020. This paper examines Cristo Rey schools, why they work, how they work and what parts of their education/business design can be successfully transferred to other Catholic high schools. It looks at the Cristo Rey Network, a cooperative organization formed to standardize the Cristo Rey approach, offer resources to the individual schools and help promote the spread of Cristo Rey schools to cities that can support them. Through interviews with founders and early backers this paper reviews the origins of the Cristo Rey method and how it has been replicated in places such as Cristo Rey Boston High School and Notre Dame Cristo Rey High School in Lawrence. And it looks to see see what lessons can be drawn by other Catholic high schools wrestling with sliding enrollment and shrinking income.