Cumberland Jr. was born into Western Pennsylvania's Negro elite, the son of Cumberland Willis Posey Sr. and Angelina "Anna" Stevens Posey of Homestead, adjacent to Pittsburgh. Posey Sr. worked on riverboats and, in 1877, became probably the first African American licensed engineer in the United States, earning a chief engineer license and the title of, "Captain." "Cap" Posey was a riverboat builder, general manager of the Dexter Coal Company, owner of the Diamond Coke and Coal Company, and industrial partner of Henry Clay Frick. He was president of the Loendi Social and Literary Club for three years and president of the Pittsburgh Courier newspaper for its first 14 years, to 1924.(Williams) The family lived in a palatial Italianate mansion on the heights.

Despite his commanding wealth, Captain Posey still had to deal with racial discrimination, according to historian William Serrin. In that crucible of race, his son began to excel as a young athlete.

In football, Cumberland Jr. was a star player and manager for semi-pro sandlot teams in the Pittsburgh area prior to 1910, including the Delaney Rifles and the Collins Tigers.

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