Instead of pursuing a career as a factory worker or mechanic, Bernie vows to "save the people" from the bad liquor that's killing them. He teams up with his brother, Joe Winghart Jr., and his sister-in-law, Mayme Schaller Winghart, to illegally sell alcohol to the masses. Known as the "Bootlegging Trio," they profit handsomely.

Even so, this formerly upstanding family from upstate New York is now part of a secret underworld of lawbreakers that includes sinister gangsters. There is danger everywhere, and Bernie is so intimidated that he vows never to marry until he's out of the business. He goes from woman to woman, breaking hearts.

Told through the perspective of the bootleggers' daughter, Bernie, You're a Bootlegger! gives a glimpse into how Prohibition affected one family and an entire nation until it was declared a failure.