The original Vanderbilt Cup, founded by William Kissam Vanderbilt II in 1904, had been one of the first major international motor races in North America. Held on Long Island's roads and later at venues including Savannah, Milwaukee, and the Santa Monica and San Francisco circuits in California, the series ran until 1916 before the United States' entry into the First World War brought it to an end. No race was held under the Vanderbilt name for the next two decades.
In 1936, William Kissam Vanderbilt II's nephew, George Washington Vanderbilt III, took up the cause and sponsored a revival of the event. The chosen venue was Roosevelt Raceway, a new circuit built on Long Island, which offered modern facilities appropriate for an international Grand Prix-level contest. A prize fund of substantial size was offered to entice the leading European teams.
The 1936 Vanderbilt Cup was run over 300 miles (approximately 480 kilometres) at Roosevelt Raceway. The prize money proved sufficient to attract major European participation: Scuderia Ferrari entered three Alfa Romeo racing cars, bringing with them the kind of competitive machinery that had been dominating European Grand Prix racing throughout the mid-1930s.
The race was won by a European driver, reflecting the superior preparation and technology of the continental entrants. American competition proved limited, and the Roosevelt Raceway course was regarded by critics as a less-than-exciting layout. Despite the problems of spectacle and competitiveness from the American side, the event drew attention as the return of a once-great racing tradition to the United States.
A second edition of the revived Vanderbilt Cup was held in 1937, again at Roosevelt Raceway and again won by a European competitor. After two runnings, however, the event was not continued. The combination of the uninspiring circuit layout, the absence of meaningful American factory competition, and the logistical challenges of bringing European teams across the Atlantic proved insufficient to sustain the series beyond its brief revival.
The 1936 and 1937 Vanderbilt Cups are notable as a rare prewar instance of top-level European Grand Prix machinery racing in the United States, predating the postwar establishment of American road racing as an internationally connected discipline. The Vanderbilt Cup name itself carried lasting prestige: in the 1960s the Sports Car Club of America revived it for several events, and in 1996 CART adopted a replica of the original trophy as the winner's prize for the U.S. 500, later designating it as the CART series championship trophy. The original cup, cast in silver and standing some 2.5 feet tall, is today held by the Smithsonian Institution, while the George Vanderbilt Cup from the 1930s revival is on display at the Museo Nicolis in Verona, Italy.