Stuff You Should Know

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Selects: The First Road Trip

Explore episode Jul 11, 2026
History
The $50 Bet That Launched the First Road Trip

Selects: The First Road Trip · Jul 11, 2026 History

Horatio Nelson Jackson put down a $50 bet at a San Francisco club that he could drive coast to coast in under 90 days — a wager worth about $1,500 at the time. Four days later, without a car, a plan, or a sponsor, he set out for New York.

Where this was said

Failed Early Attempts: The Davises and Alexander Winton

At 15:55 · chapter starts 9:30

Car manufacturers quickly realized that a successful coast-to-coast drive would be priceless publicity. The first real attempt, in 1899, starred John and Louise Davis in a Duryea car sponsored by the National Motor Carriage Company. It was a PR catastrophe: they were beaten to Syracuse, New York, by a one-armed bicyclist who had been given a 10-day head start. Press coverage evaporated after Chicago. Then in 1901, Winton himself — with his publicist — tried heading from west to east (smart: tackle the hardest terrain while the car is fresh). His undoing was the Nevada desert, where sand clogged carburetors and oil systems and ultimately bogged them down entirely. Yet both failures generated enough publicity to confirm: whoever actually completed the crossing would be famous.

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