Full Story - Wiretap

Roy Olmstead ran bootlegging like a corporation. Boats, drivers, warehouses, payroll — all of it organized, professional, and for years completely untouchable. He paid his people well and refused to deal in violence. Law enforcement couldn't find an angle. So they tapped his phone instead, pioneering one of the first uses of wiretapping in American criminal prosecution. The case went all the way to the Supreme Court. He lost. He served his time, walked out, and never looked back.