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Why Are Cuban Cigars Illegal in the US?

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Ah, the mythical Cuban cigar. Nothing is more coveted and sought after in the cigar aficionado community.


The very mention of the words sends one into thoughts of toasting subtle notes of mahogany, relaxing on a Havana beach rocking a guayabera and fedora.


Although it deserves the accolades it enjoys, the legendary Cuban cigar also has an interesting and complicated history with the United States.

So...Why Are Cuban Cigars Illegal in the US?

Cuban cigars are illegal in the United States because of the strict trade embargo to ban all imports of products containing Cuban goods. The embargo was established in February 1962 by President John F Kennedy to counter Fidel Castro's communist regime in Cuba.


At one point in time, getting caught attempting to smuggle a Cuban cigar through U.S. customs would've cost you a fine of up to $55,000!


This ban is part of the allure and nostalgia associated with the Cuban cigar. Simply put, people want what they can't or aren't supposed to have.


Keep reading to unwrap the mystery of the tough relations between Cuba and the U.S.

The Cuban Revolution and Fidel Castro's Rise to Power

We can't talk about the history of Cuban cigars without mentioning Fidel Alejandro Castro Ruz, or "El Caballo", as native Cubans call him. A devout believer in Marxism–Leninism, Castro sought to further socialism and Marxism in Cuba.


In Castro's view, the Cuban politicians had given to much control to the imperialistic United States. This lead to 1953 Castro attempting to overthrow the Cuban government and President Fulgencio Batista by leading a failed assault on Moncada Barracks. 


Fidel finally snatched power and was sworn in as Prime Minister on February 16, 1959. From there he began to consolidate his power and confiscate land and business owned by rich Cuban citizens and foreigners.

The Divide Grows Deeper

After assuming the role of Prime Minister In 1959, Castro set out to the US to a so-called "charm-offensive", that was anything but. President Dwight D. Eisenhower refused to meet with Castro furthering his disdain for the United States.


Instead, Eisenhower sent his Vice President, Richard Nixon, to meet with Castro. It is said that Fidel had an immediate dislike for Nixon -- Good eye? Maybe. "Game peeps game? Who knows?


Next was what is known as "The Bay of Pigs Invasion". This was an attempt to project power by landing a ship to form a beachhead on the shores of Cuba. This attempt failed and further agitated the Cold War between the US and the Soviet Union with Cuba in the middle of it all.


At the height of the Cold War, the tension flared between the U.S. and Cuba with the onset of the "Cuban Missile Crisis" in October 1962. The Missile Crisis was a 13-day standoff between the US and the Soviet Union.


The confrontation began when the US discovered that U.S.S.R. had positioned ballistic missiles in Cuba. This conflict is widely considered the closest time the world came to nuclear war.

JFK smoking a cigar

Yes President John F Kennedy loved his Cuban cigars as well, even during the Cuban Missile Crisis

The U.S. Trade Embargo Against Cuba

The anti-communist push that began in Eisenhower's administration only strengthened in Kennedy's as Cuba became closer to the United States' fiercest geopolitical enemy, Russia.


In 1962, by Executive Order, John F. Kennedy increased measures of the embargo by broadening the scope of restrictions. This included a restriction on goods of cuban origin, regardless of whether they were manufactured or constructed outside of Cuba.


But get this, before he made the Executive Order, he instructed one of his officials, Pierre Salinger to bring him back 1000 H. Upmann cigars from Cuba. Well, his Head of Press outdid himself and brought back 1200 of the soon to-be-rare commodity.


Moments after Salinger's return, Kennedy announced the new restriction that now made Cuban cigars illegal contraband.


Since 2018, the trade embargo with Cuba is strongly enforced by six primary statutes:

  • Trading with the Enemy Act of 1917 (banning arms trading)
  • Foreign Assistance Act of 1961 (maintaining the ban unless movement towards democratization)
  • Cuban Assets Control Regulations of 1963 (domestic embargo enforcement)
  • Cuban Democracy Act of 1992 (sanctions geared towards the peaceful transition to democracy)
  • Helms-Burton Act of 1996 (extension of the embargo to countries that trade with Cuba)
  • Trade Sanctions Reform and Export Enhancement Act of 2000

The Poison Cigar and 637 Other Ways To Assassinate Castro

Fidel castro cigar aficionado

Fidel quit smoking by this time but still appreciated the cigar culture

Castro was a well-known cigar lover. And being in Cuba he was in the land of riches. In the 1960s the CIA launched a covert operation to topple the Cuban government. The code name was super cool: Operation Mongoose. James Bond would be jealous.


As legend has it, the plan was to get Castro to smoke a cigar laced with a potent poison called botulinum toxin. But it never reached Fidel's lips.


In a cartoonish manner, the United States attempted to kill "El Caballo" with an exploding cigar! Bugs Bunny would be proud. Other zany attempts include a scuba diving suit tubercle bacilli and a booby trap conch on the bottom of the sea where he dove. Man, this stuff is so crazy you can't make it up!


Many believed that the embargo would be removed after Fidel Castro's death, but this was not the case.

"Fidel Castro eluded over 600 assassination attempts including one by the United States to kill him by poison cigar!"

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The Obama Administration Loosens The Trade Embargo

Although the trade embargo was still in place, American citizens were allowed to legally bring $100 worth of Cuban cigars into the United States. In 2014 the restriction on bringing Cuban cigars into the U.S. was eased by President Barack Obama's Administration.


2016 saw this $100 limitation removed and at that time there was no limit to the amount that you could carry through US Customs. However, there was a catch.


According to those regulations, commercial importers returning with Cuban goods have to formally declare their goods starting at the $2500 entry-level.


The point is you did not want to look like your selling "Cubanos" in the Little Havana section of Miami as soon as you jump out of your Uber. You simply just had to not overdo it - at least not past the $2,500 worth of goods.


Also, you had to purchase the cigars from independent Cuban merchants. As I've mentioned, the entire Cuban cigar industry is run by the state. You're officially in the "books". So bringing more than that through U.S. Customs could have aroused suspicions.

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Trump Tightens The Trade Embargo Once Again

Can you bring Cuban cigars into the United States legally?

 

The regulations that were loosened by the previous administration were tightened once again under the Trump administration. As of 2020 The United States prohibits the importation of Cuban tobacco, Cuban cigars and Cuban rum for Americans returning from Cuba or any other country maintaining free trade with Cuba like Mexico, Canada or the UK.


In 2020 the “Cuba Prohibited Accommodations List” was created by the US State Department that contains the list of names and addresses of hotel properties in Cuba where U.S. citizens can no longer legally do business - like book a room for example.


As it is written in the new regulations, “no person subject to U.S. jurisdiction may lodge, pay for lodging, or otherwise make any reservation for or on behalf of a third party to lodge, at any property in Cuba that the Secretary of State has identified as a property that is owned or controlled by the Cuban government, [or] a prohibited official of the Government of Cuba”.


This has effectively made over 400 hotels and lodging properties off limits to U.S. travelers because the Cuban government controls all major hotels on the island. 


This embargo against Cuba forces U.S. travelers to look for privately help lodging such as the ones found through online apps like AIrBnB or VRBO. Thus making the times feel more reminiscent of February 1962 than 2022.


There has been much backlash from travel providers and globe trotters alike. As a result of these strict regulations, cuban cigar loving citizens from the United States will be deterred from attending yearly events such as the prestigious Habanos Festival and the world renowned Havana Jazz Festival. 

Cohiba Cuban Cigars

The world renown Cohiba "Cubano"

Cohiba and Other Cuban Cigar Brands

By far, cigars are Cuba's most precious export. And perhaps the most famous cigar brand in the world, Cohiba was established as a private limited production. Cohiba was created to supply Fidel Castro and his cohorts with premium "stogies" and what is now coveted cuban tobacco.


The cigar began to take on a cult-like following as they were often handed out as gifts to diplomats. Thus, they have been a state-run cigar industry since their inception.


In 1982 Cohiba began to sell their cigars commercially. The cigars more premium selections have garnered the some of highest marks from world-renown critics.


Fitting the pattern of constant conflict, Cohiba has been in a patent fight with the US maker of the same name for decades.


Other highly sought after Cuban cigar brands include:

  • Romeo y Julieta
  • Bolivar, Montecristo
  • Partagas
  • and the aforementioned H Upmann

However, according to the U.S. International Trade Commission, "Cuba's tobacco sector is fully state-controlled".

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The Future of Cuban Cigars in the U.S.

The future of Cuban cigars in America is unclear. You can't even be certain of the ones that make it to the US. 95% of all Cuban cigars in America are reported to be counterfeit.


And if you are thinking about getting "slick", the purchase of cuban cigars, cuban tobacco or rum (anything of cuban origin) through mail-order or online stores continues to be strictly prohibited.


A USA Today poll in 2008 showed that 61% of Americans believe that relations "should" be re-engagement with Cuba.


However, Cuban Americans show a declining support for reconnecting with the "fatherland". And having lived in Miami for 2 years I can definitely testify that this is true. There is not a lot of love for Castro and the communist regime in South Florida.


There are groups that promote the re-engagement with Cuba like Engage Cuba. So the hope is still alive to make the world's favorite cigars completely legal in the U.S.


Until then, my cigar lovers, keep stuffing your bags full of those coveted "sticks"!


- Jack


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Jack Cullum

Jack Cullum aka "The Box Man" is known to bust a box or two open! He is super into it really! He is also the lead writer for Subscription Boxes for Men. So please connect with him on social and may all your boxes be great!

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