One morning last September, Tommie Lindsey awoke to a phone call that was so shocking he thought he was still dreaming. On the other line, a stranger from Chicago said he’d been awarded $500,000 for the creativity and promise he’d shown during 15 years as a public school speech and debate teacher in a working-class suburb of San Francisco.

Then, as quickly as this mysterious benefactor had appeared, he was gone. He told Lindsey that he’d never hear from him again. He was free to use the money...

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