On 7 February 1962, United States President John F. Kennedy imposed a trade embargo on Cuba to sanction Fidel Castro’s communist government. According to Pierre Salinger, then Kennedy’s press secretary, the president ordered him on the evening of 6 February to obtain 1,200 H. Upmann brand petit corona Cuban cigars; upon Salinger’s arrival with the cigars the following morning, Kennedy signed the executive order which put the embargo into effect. Richard Goodwin, a White House assistant to Presidents Kennedy and Johnson, revealed in a 2000 New York Times article that in early 1962, JFK told him, “We tried to exempt cigars, but the cigar manufacturers in Tampa objected.”

The embargo prohibited US residents from legally purchasing Cuban cigars and American cigar manufacturers from importing Cuban tobacco. As a result, Cuba was deprived of its major customer for tobacco, and American cigar manufacturers either had to find an alternative source of tobacco or go out of business.

In the United States, authentic Cuban-made cigars are seen as “forbidden fruit” for Americans to purchase. Upon the expropriation of private property in Cuba, many former Cuban cigar manufacturers moved to other countries (primarily the Dominican Republic) to continue production. The Dominican Republic’s production of tobacco grew significantly as a result. After reallocation, most Cuban manufacturers continued to use their known company name, seed, and harvesting technique while Cubatabaco, Cuba’s state tobacco monopoly after the Revolution, independently continued production of cigars using the former private company names. As a result, cigar name brands like Romeo y Julieta, La Gloria Cubana, Montecristo, and H. Upmann among others, exist in both Cuba and the Dominican Republic. Honduras and Nicaragua are also mass manufacturers of cigars. Some Cuban refugees make cigars in the U.S. and advertise them as “Cuban” cigars, using the argument that the cigars are made by Cubans.

Advertisement aimed at American tourists for Cuban Cigars in Niagara Falls, Ontario, minutes away from the US–Canadian border. It remains illegal for US residents to purchase or import Cuban cigars, regardless of where they are in the world, although they are readily available across the northern border in Canada and the southern border in Mexico. While Cuban cigars are smuggled into the USA and sold at high prices, counterfeiting is rife; it has been said that 95% of Cuban cigars sold in the US are counterfeit. Although Cuban cigars cannot legally be imported into the US, the advent of the Internet has made it much easier for people in the United States to purchase cigars online from other countries, especially when shipped without bands. Cuban cigars are openly advertised in some European tourist regions, catering to the American market, even though it is illegal to advertise tobacco in most European regions.

The loosening of the embargo in January 2015 included a provision that allowed the importation into the U.S. of $100’s worth of alcohol or tobacco per traveller, allowing legal importation for the first time since the ban.