In 1958, a New York man named Robert Lane decided to call his baby son Winner. The Lanes, who lived in a housing project in Harlem, already had several children, each with a fairly typical name. But this boy – well, Robert Lane apparently had a special feeling about this one. Winner Lane: how could he fail with a name like that?

Three years later, the Lanes had another baby boy, their seventh and last child. For reasons that no one can quite pin today, Robert decided to name this boy Loser. It doesn’t appear that Robert was unhappy about the new baby; he just seemed to get a kick out of the name’s bookend effect. First a Winner, now a Loser. But if Winner Lane could hardly be expected to fail, how could Looser Lane possibly succeed?

Loser Lane did in fact succeed. He went to prep school on a scholarship, graduated from Lafayette College in Pennsylvania, and joined NYPD (it was his mother’s longtime wish). Although he never hid his name, people were uncomfortable using it. “So I have a bunch of names,” he says today, “from Jimmy to James to whatever they want to call you. But they rarely call you Loser.” Once in a while, he said, “they throw a French twist on it: ‘Losier.’” To his cop friends he is known as Lou.

And what of his brother with the can’t-miss name? The most noteworthy achievement of Winner Lane, how in his mid forties, is the length of his criminal record: almost three dozen arrests for burglary, domestic violence, trespassing, resisting arrest, and other mayhem.

These days Loser and Winner barely speak. The father who named them is no longer alive. Clearly, he had the right idea – that naming is destiny – but he must have gotten the boys mixed up.

Source - Freakonomics, page 163

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