Matthew Heywood Jackson, Sr. (1877–1929) was a Chicago-based letter carrier, Prince Hall Masonic leader, and devoted family man whose life connected Atlanta’s Black professional circles with the Great Migration North. He met his future wife, educator Ruth Jackson, on the campus of Atlanta University, and together they raised daughters who continued the family’s scholarly and civic legacy. In Illinois, Jackson rose to Deputy Grand Master of the Prince Hall Grand Lodge and chaired the board that built the Prince Hall Masonic Home in Rock Island. He is remembered for his steady service, organizational leadership, and the foundation he laid for the Jackson family’s multigenerational impact.