Alexander Winton started a small bicycle business in Cleveland, Ohio, but the coming of the automobile had an irresistible appeal to him and by 1895 he had made his first petrol-powered motor-bicycle. Then in September 1896 he produced his first car which was a vertical twin with friction transmission. In 1897 he formed the Winton Motor Carriage Company and produced his second car. A year later production reached 21 which obviously went to Winton's head because he engaged in a war of words with Fernand Charron about the relative merits of American and French cars and ended up challenging Charron to a 1,000 mile race. Charron put up 20,000 francs but the duel never took place.

At this point, James Gordon Bennett enters the story. He was the Paris-based proprietor of the New York Herald who was best known for sending Henry Stanley to find David Livingstone in Africa, but had also contributed a substantial sum towards the prize money for the 1895 Paris-Bordeaux race (as had a certain William K. Vanderbilt - but that is another story!). Anyway, Bennett was anxious to encourage foreign countries (especially his native United States) to put up a fight against the limitless number of successes attained by French car manufacturers in the road races that were taking place. When he heard about Winton's challenge, he thought that if some valuable trophy were put up for competition, foreign manufacturers would be attracted and might possibly bring the long string of French victories to an end.

So in November 1899 he wrote to the foreign automobile clubs saying he wanted to encourage the automobile industry and was creating an international prize to be competed for by the various automobile clubs of the world. He put the matter in the hands of the Sporting Committee of the Automobile Club de France who drew up a set of 28 rules (the first ever 'formula') which he approved. The club wanted the prize to be named after its donor, but Bennett said he preferred it to be called the 'International Trophy' or 'La Coupe Internationale'. This wish was never obeyed and the races are always remembered as the Gordon Bennett Cup (or Trophy).