Oldfield's new car, called the "999," had no springs or shocks, and was steered by a tiller, not a wheel. Cooper found that the unwieldy machine, almost impossible to turn or control, needed "a wrestler more than a driver," according to Timothy Messer-Kruse in Toledo's Attic. This role was perfect for Oldfield, and, as Messer Kruse wrote, in the Manufacturer's Challenge Cup, "Oldfield wrenched the car around the turns in a sliding cloud of dust that became his trademark and discovered his talent at last." He beat defending champion Mexander Winton by a half-mile in his first race.
On Memorial Day in 1903, Oldfield became the first person to drive a mile in a minute flat, and won another race. Two months later, he drove a mile in 55.8 seconds, leading his former competitor, Winton, to hire Oldfield to drive for him. Oldfield was given a salary, expenses, and free cars. He toured the United States, doing match races and speed runs; one year, competing for the Peerless company, he competed on twenty different tracks in eighteen weeks. He gave four exhibition runs and won sixteen match races in a row. When asked by a reporter from Automobile what it felt like to drive a mile in less than a minute, Oldfield said, "There is an exhilaration in driving fast that I cannot resist: it is like intoxication."
In 1910, Oldfield bought a Benz and broke all speed records for the mile, two miles, and the kilometer at Ormond Beach, Florida. With the fame these feats brought him, he began charging $4,000 for each personal appearance.
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