Cumberland “Cap” Willis Posey Sr. was born to enslaved parents on August 13, 1858, near the Port Tobacco River in Charles County, Maryland. His mother died in 1865 when Posey was seven years old. Soon after, Posey and his two siblings moved to Winchester, Virginia, where their father worked as a minister for African Methodist Episcopal (AME) churches. After two years in Winchester, the family moved to Belpre, Ohio, close to Parkersburg, West Virginia, where Posey’s father passed away in 1874. While in Belpre, Posey was employed by a steamboat owner named Mr. Payton who Posey most likely lived with. While working on Payton’s ship, the Magnolia, Posey studied the engineers at work and made it his goal to run the engine room one day. He achieved that dream thanks to Payton, who helped Posey secure a job as an assistant engineer on the Striker. At age twenty, Posey became the first African American to hold a chief engineer’s license and he worked in that capacity for fourteen years. During his career as an engine room operator, he was given the nickname “Cap.”

While working as an engineer, Posey met his wife Angeline “Anna” Stevens, a schoolteacher in Athens, Ohio. The two were married in 1883, and the couple moved to Homestead, south of the city of Pittsburgh, in 1892.

That same year, members of the Amalgamated Association of Iron and Steel Workers struck at the Homestead Steel Works, owned by Andrew Carnegie, due to the company’s attempts to scale back workers’ wages. Carnegie hired the Pinkertons to break up the strike, but the workers fought back. The ensuing clash caused several deaths. After the violence, the Pennsylvania National Guard was called to repress the strike.

The Homestead Strike marked a major setback for labor interests in the region. In its wake, Posey started his own coal mining operation, the Delta Coal Company. Soon after, he sold his shares to create the Posey Coal Dealers and Steamboat Builders. It is said he partnered with Henry Frick and supplied Carnegie Steel with African American workers, replacing those who had participated in the strike. This relationship helped propel Posey’s career and got Black workers into the Homestead plant. 

The Posey Coal Dealers and Steamboat Builders was reported by the Pittsburgh Courier to have built forty-one steamboats by the time of Posey’s death. Using funds from this company, he became a major shareholder in the Marine Coal Company and was hired to manage it. His business life did not unfold without controversy, however. In 1897, he, along with others, were investigated and brought to court over a suspected conspiracy to defraud the Shoenberger Steel Company through their dealings with coal. The court found Posey guilty a year later and sentenced him to fifteen months at a workhouse. Due to his success as a business owner, though, Posey and his wife moved into one of the most luxurious houses in Homestead, which was a significant achievement for an African American family at the time.

In 1910, Posey was given the chance to invest in a fledgling newspaper, the Courier, started by the poet/security guard Nathaniel Harleston. Seeing potential in the paper, Posey and three other influential businessmen transformed it into the Pittsburgh Courier, one of the first black-run newspapers in the country. Posey was President of the Pittsburgh Courier for fourteen years. He also held positions in other local businesses such as the Douglas Land and Investment Company and the Modern Savings and Trust Company. 

Posey was a highly influential figure in Pittsburgh’s African American community and one of the wealthiest African Americans in the United States at the time. Alongside his business ventures, he also served as President of the board of directors of the Warren AME church for fifteen years. He was a member of various organizations, including The True Reformers, the Masons, the Knights of Pythias, Knights Templar, the Odd Fellows, the Household of Ruth, "St. Luke’s" (possibly an insurance organization), the Young Men’s Christian Association, and the Loendi Club, the last of which he was president for three years. 

Posey passed away on June 12, 1925, due to an illness, and was buried with full Masonic honors. He left behind a legacy of entrepreneurial success despite his beginnings as the child of enslaved parents and as an African American man living during the Jim Crow era. He was survived by his second wife, Bessie Posey, two sons, S.H. Posey and Cumberland Willis Posey, Jr., a daughter, Beatrice Baker, and a stepson, W.F. Page. Cumberland "Cum" Posey became an influential figure in the African American baseball scene in Pittsburgh.