The increase of underprepared students entering college decreases persistence and graduation rates at postsecondary institutions, ultimately declining degree attainment and social mobility of American citizens (U.S. Department of Education, 2016; McGuire, 2018). ACT, Inc. (2017) data suggests that overwhelming percentages of high school graduates are academically underprepared and are not college-ready. Moreover, an overwhelming number of academically underprepared students come from historically underrepresented populations. To help increase access and college readiness among these populations, specialized programs and services must be implemented to ensure these students are successful at the college level. The Dr. Charles W. Donaldson Scholars Academy is a specialized program and direct result of a $10 million desegregation settlement from the 30-year-old "Little Rock School District et al. v. Pulaski County Special School District et al." (1982-2014) case. The purpose of the qualitative cross-case comparison study is to understand and evaluate the effectiveness of a program that is designed to increase college readiness, persistence, student success, and graduation rates for underprepared students in the state of Arkansas, in particular the Pulaski County Special School District. This qualitative cross-case comparison study interviewed eight program participants to investigate how the program Dr. Charles W. Donaldson Scholars Academy influenced their persistence and graduation rates at a predominantly White university and historically Black college. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]