When Harold “Carload” Ritchie died in 1933, Time magazine’s obituary noted that “he had good claim to the proud title of ‘World’s Greatest Salesman.’” He was one of the richest men in Canada, and owned the largest sales network in the world. Yet little is known about him. He wasn’t part of the Canadian establishment, though the companies he came to own were more profitable than most of the country’s banks. He was born on Manitoulin Island, and in many ways, remaining on an island of his own making. Through Harold’s enigmatic life, we glimpse both the country in the first decades of the twentieth century, and the entertaining birth of the pharmaceutical industry.