William Kissam Vanderbilt II

That same year, he launched the Vanderbilt Cup, the first major trophy in American auto racing. An international event, designed to spur American manufacturers into racing, the race's large cash prize drew the top drivers and their vehicles from across the Atlantic Ocean who had competed in Europe's Gordon Bennett Cup. Held at a course set out in Nassau County on Long Island, New York, the race drew large crowds hoping to see an American car defeat the mighty European vehicles. However, a French Panhard vehicle won the race and fans would have to wait until 1908 when 23-year-old George Robertson of Garden City, New York became the first American to win the Vanderbilt Cup.

While a great part of his life was filled with travel and leisure activities, Willie K Vanderbilt's father put him to work at the family's New York Central Railroad offices at Grand Central Station in Manhattan. Read Less

Seeing the potential to solve the safety issue as well as improve attendance to his race, Willie K Vanderbilt formed a corporation to build the Long Island Motor Parkway, one of the country's first modern paved parkways that could not only be used for the race but would open up Long Island for easy access and economic development. Construction began in 1907 of the multi-million dollar toll highway that was to run from the Kissena Corridor in Queens County over numerous bridges and overpasses to Lake Ronkonkoma, a distance of. However, the toll road was never able to generate sustainable profits and in 1938 it was formally ceded to the county governments in lieu of the $80,000 due in back taxes. Read Less