The underachievement of African Americans, particularly African-American males, is one of the most troubling issues in education (Cokley et al., 2012; Schott Foundation, 2018). A significant population of African-American males has struggled to find their place in society (Wilson, 2014). Recent data shows 78% of African American students are completing high school in Chicago, Illinois (Casey Foundation, 2021). While the number of African American students who have graduated has risen in the last five years, African American males have not kept pace with African American female students and peers from different racial groups (Pearman et al., 2019). This study examined strategies that support the achievement of African American males in Northern Chicago high schools. The researcher gathered data through interviews with recent African American male graduates or seniors over the age of 18 who could explain personal experiences and strategies that impacted their academic success. Data were analyzed using open coding. Patterns and themes such as racial identity and support systems were identified as part of the data analysis process. Critical race theory (CRT) is the guiding theoretical framework used in examining the conceptualization of race and racism’s role in educational systems, practices, and outcomes. The results from this study can provide further and deeper understanding on strategies that may improve the educational attainment of African American males in northern Chicago high schools. Based on the findings, strategies identified in the study, used by African American males, other students of different ethnic groups, educational practitioners, researchers, parents, policymakers, and community leaders may bring positive social change to continue increasing graduation rates in northern Chicago schools.