It is not certain who was actually the first person to introduce the numbers game into the daily life in Harlem. Some believe that it was the famous philanthropist, Casper Holstein, or a woman known as Harlems Policy Queen, Stephanie St. Clair.
Casper Holstein and his mother immigrated to Harlem in 1894 from St. Croix in the West Indies. He attended high school in Brooklyn and served in the U.S. Navy. After his term in the Navy, Holstein managed to find work as a porter and bellhop for a Wall Street brokerage firm. While there, he cultivated an interest in the stock market and began studying the system and its numbers. In his Playing the Numbers, Redding credits Holstein for starting the numbers game: Came the day when, studying clearing house totals, an idea struck Holstein between the eyes. Tradition has it that sitting in his airless janitors closet, surrounded by brooms and mops, he let out an uproarious laugh, and in general acted like a drunken man.
Holstein became known as The Bolito King and went on to amass a vast fortune through the numbers game. But he was not selfish with his wealth. He became a humanitarian and philanthropist, building dormitories at black colleges, donating money to black causes, supporting a Baptist school in Liberia and many of Harlems poor children, contributing to black artists, publications and numerous charities, establishing hurricane relief funds for the Virgin Islands and founding a museum. Casper Holsteins wealth was estimated to be at least well over $2 million, from having operated a numbers game. Some say his income averaged almost $12,000 a day. Redding, in his Playing the Numbers, says about Holstein, In a year he owned three of the finest apartment buildings in Harlem, a fleet of expensive cars, a home on Long Island, and several thousand acres of farmland in Virginia. It did not take long for Casper Holsteins success to take a strange turn.