An original native of St. Croix, Virgin Islands, Holstein got his start in the numbers game on Wall Street. After a stint in the Navy and working as a porter and a doorman, Holstein worked his way to Wall Street as head messenger for a brokerage firm. While on the street, he studied the stock market and familiarized himself with numbers. Like many poor people of the time, he took his knowledge to the gangs, earning a living by running an illegal lottery he nicknamed Bolito. By 1920, the kid from the West Indies had become the “Bolito King,” head of the most successful underground lottery system of the time.