Moonshine Over Harlem

After a brief appearence at a school, Charlie - a gang member in the 1930s and 1940s - is killed. Othniel tells him that he has redeemed his bad ways ever since, but that he can get a second chance anyway, to solve his conflict with the love of his life, Rose.
Mr Smith follows Charlie back to Harlem during the Prohibition era, where Charlies interracial relationship to Rose is something strange and frowned upon. But the real problem is that Rose's father is with the FBI, and that Rose will turn Charlie in. Now Charlie must somehow convince himself to get out before the deal that will be raided by the FBI, or get Rose to not turn him in.

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S02E17 - Daddy's Girl