The COVID-19 pandemic has had a significant financial impact on land-grant historically Black colleges and universities (HBCUs) in North Carolina, South Carolina, and Georgia, which have historically faced underfunding by their respective state governments. This study examined the issue of low engagement rates and alumni giving among former student leader alumni at these institutions, focusing on their perceptions of the factors that influence their engagement and philanthropic behavior, guided by Arroyo's and Gasman's HBCU educational approach for Black college student success. Using a qualitative multicase study design, the research targeted three specific HBCUs and involved 19 alumni who provided their insights through questionnaires and semi-structured interviews. To ensure the reliability of the findings, member checking was utilized to validate participant responses, and NVivo qualitative software aided in data analysis. The findings indicate that academic and social factors are key influencers of alumni engagement and giving among alumni student leaders at land-grant HBCUs. Recommendations include enhancing student engagement programs to facilitate meaningful interaction with faculty and advisors, promoting a sense of belonging during the undergraduate experience, and supporting personal growth during the undergraduate experience, all of which will lead to increased alumni engagement and giving. The study's implications aim to offer valuable insights for land-grant HBCUs to better understand the academic and social experiences of their former student leader alumni and how these experiences impact their engagement and giving behaviors. [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.]