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When Charles Vance Miller died on Halloween 1926, few could have predicted the bizarre legacy this childless Toronto lawyer would leave behind. Born to humble farming parents, Miller had built an empire through shrewd investments in breweries, silver mines, and racehorses, becoming one of Canada's wealthiest bachelors. But without heirs or close relationships, his true lasting impact would come through what he called his "necessarily uncommon and capricious" will.

Miller's will became notorious for its mischievous provisions. He left brewery shares to temperance-preaching ministers, jockey club ownership to anti-gambling clergymen, and forced three men who likely despised each other to co-own his vacation home until the last one died. Yet his most extraordinary stipulation—which would become known as "The Great Stork Derby"—offered roughly $500,000 (about $12 million today) to the Toronto woman who gave birth to the most children in the decade following his death.

What began as an obscure provision in a will evolved into a public spectacle that laid bare the tensions of 1930s Toronto society. Newspapers published "racing cards" tracking mothers' progress, while courtroom battles determined which children "counted," revealing deep prejudices about legitimacy, immigration, and women's autonomy. When a woman who had left an abusive husband found herself disqualified despite bearing ten children, and another lost standing because her child was stillborn, the darker implications of Miller's game became apparent.

The final ruling in 1936 declared four women joint winners, each receiving approximately $2 million in today's currency. Surprisingly, these mothers used their windfalls responsibly—purchasing homes and providing education for their large families. But the ethical questions linger: Was Miller's contest a cruel manipulation of vulnerable women or a unique form of philanthropy? And what does our continued fascination with this story reveal about our own attitudes toward wealth, family, and posthumous power?

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