Trading with the Enemy follows an American looking to make a fast buck in Cuban’s illegal cigar trade. Fat cats back home clamor for the forbidden tobacco, and Terry knows just how to get it. From Austin, Texas to Havana, Cuba, our guide Terry shows us the ropes of this black market bonanza. But cigars aren’t all that he’s after, many young women of Havana have a lucrative business of their own befriending tourists like Terry. The lines between business and pleasure, and between tragedy and comedy, have never been so tangled.