Caspar Holstein was born on December 7, 1875 in Christiansted, St. Croix, Danish West Indies (presently known as the U.S. Virgin Islands). His paternal grandfather was a White, Danish officer of the Danish West Indies colonial military and his paternal grandmother was a Black woman of Africa. Their son, Caspar’s father, would become a landowner, making him well-to-do. Caspar’s mother, Emily, was a Black woman of the island country and would be his primary parent.
In 1877, when Caspar was only two years old, Mary Thomas led thousands of Black workers in a rebellion against Dutch colonialism. Although slavery had been abolished in 1848, Blacks continued to suffer hellish conditions. Thomas, known as Queen Mary, directed an insurrection which burned down Fredericksted and the entire western region of St. Croix. This event would forever impact Caspar, greater increasing his love for his people and island nation. Author Axel C. Hansen, in his From These Shores, detailed, “The harsh and inhumane treatment of the masses left an unforgettable imprint on the mind of young Caspar.”
In 1888, Emily and Caspar immigrated to New York City. Living in the Harlem community of the Manhattan borough, he attended elementary and secondary school in the Brooklyn borough, where he graduated from the Boys High School. After graduation, his mother passed away. Holstein attained work as a bellhop and in this position, he first learned the rules of gambling. In 1898, he enlisted in the U.S. Navy and was stationed on the U.S.S. Saratoga. Upon completing four and one-half years of service, he returned to New York City where he worked various jobs, including as a custodian, bellhop, doorman and, eventually, head messenger for a brokerage firm on Wall Street.
It was during this time that he became acquainted with the Chrystie family. In being asked to run an errand by Fannie, the wife of John, Caspar was given the wrong information. Using his resourcefulness, he was able to complete the errand. This impressed Fannie, who hired Caspar to read to the family’s grandmother, who was blind. He was later employed, most likely as a custodian, by John, a successful and wealthy bank on Wall Street. It was here where Holstein was introduced to the stock market.
During his time of working on Wall Street, Caspar Holstein began studying the stock market. He also mastered the principles of the “numbers” system, a victimless but illegal (as of 1901) lottery. Many Blacks of all socioeconomic status, but especially those impoverished, in New York City “played the numbers”.