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Throughout the life of Harry S. Cummings, he was a man who achieved a lot of great things during his time of living. One important accomplishment was becoming the first colored City Councilman for Baltimore City. Cummings was considered a very influential person of his time. He was not the only Cummings in his family that had surpassed barriers and achieved astounding accomplishments. His siblings Aaron Cummings and Ida Cummings also exceeded barriers and expectations of colored people during this time. Aaron became the first colored United States Postal Service in Baltimore City. In like manner, Ida Cummings became one of the first colored kindergarten teacher in Baltimore City. Aside from his professional career,  Harry was also a husband and a father that had a family awaiting his arrival at home. Cummings married Blanche Teresa Conklin and had two children, named Harry Sythe Cummings Jr. And Louise Virginia Cummings Dorcas. Cummings was very active in his career and served as councilman until his death in 1917. His cause of death was a complication of diseases.