1. Bourbon is an American whiskey, which is the "American made" part. Cohibas are a cigar brand from Cuba, a country famous for cigars. "American won" likely refers to the Cohibas cigars being gained from Cuba. Think of "won" like in the phrase "win a prize". It could also mean the military/political conflict between the US and Cuba.
2. Many people commit suicides by jumping off high led