Stuff You Should Know

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Selects: The First Road Trip

Explore episode Jul 11, 2026

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Horatio Nelson Jackson: The Man Behind the Bet

At 17:35 · chapter starts 16:00

The star of the story is Horatio Nelson Jackson: a doctor who contracted tuberculosis, gave up medicine, married the wealthy Bertha Richardson Wells (whose New England family made their money in celery compounds), and settled into a life of comfortable adventure. By 1903 he was a devoted car enthusiast and collector. At the University Club of San Francisco, when fellow members dismissed automobiles as useless, Jackson defended their honor with a $50 wager — worth about $1,500 at the time — that he could drive from San Francisco to New York in under 90 days. The bet was accepted on the spot. Four days later he was on the road, having only just purchased the car. His wife, whom he addressed in letters as 'My dearest Swipes,' took a train to Burlington and wished him well. The letters home, voiced in the documentary by Tom Hanks, paint a picture of a warm, loving couple — and a man who approached the whole enterprise with infectious good cheer.

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