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This working paper explores the relationship between historical redlining and present-day digital disparities in Black communities, focusing on three cities in Texas, California, and Illinois. Using Geographic Information Systems (GIS), the study overlays historical redlining maps with current Digital Divide Index (DDI) data to identify patterns of digital redlining. Grounded in Digital Capital Theory and Critical Race Theory, it examines how structural racism and limited digital access impact educational, economic, and technological opportunities, such as artificial intelligence.