Wynn, a woman of privilege with a background in journalism, first entered Rikers—also known as "the Rock"—to do research for a story about a con man for her newspaper. But, once inside this compelling world, Wynn felt a need to return, because, she says, the men she met defied her stereotypes of criminals, and perhaps also because she knew that whatever she had to offer, it would be eagerly received. She became a teacher in a unique rehabilitation program known as Fresh Start, run by the Osborne Association. The Osborne Association was named for its founder, an early New York prison reformer who lived for a week as a convict in Auburn Prison so that he could know what the inmates' daily lives were like. He did this after accepting the job of warden for that renowned institution.