When it comes to American cigars, Cuban cigars have long had a storied history, thanks in part to their illegal stature. They’ve been known as the forbidden fruit of tobacco, yet ever since the early 1960s they’ve been lauded, and controversial. But the reasons behind them being illegal, and what’s changed, aren’t exactly what most people think.
It’s a tale rooted in the Cold War, a trading embargo that sent ten United States presidents on a rollercoaster ride, present-day politics, and shifting diplomatic relations.
Thus, while things have certainly changed in recent years, it’s a lot more complicated for those who haven’t kept track of ever-changing regulations.
When Politics and Premium Tobacco Collide
Cuban cigars didn’t become illegal because of any action taken by their manufacturers. Instead, in 1962, John F. Kennedy signed a comprehensive trade embargo against Cuba – and effectively all things Cuban.
Cuba had become an ally of the Soviet Union during the Cold War and JFK was not about to allow Americans to support the enemy with their hard-earned cash. Thus, Americans were prohibited from buying, importing, or bringing Cuban products to America when traveling abroad. This meant rum, art, pottery, and cigars, the most famous product of all.
Ironically, just before JFK signed that embargo, he allegedly had his press secretary buy out a Havana tobacco shop with 1,200 Cuban cigars for his private collection. Thus, during the history of cigar enthusiasts, whenever the topic comes up, the irony isn’t lost that one of America’s greatest presidents appreciated Cuban cigars but broke no laws in expediting a beautiful collection for himself.
For the next fifty-plus years, Americans were not allowed to even possess Cuban cigars since doing so could lead to civil punishment with fines. Yet Cuba’s black-market value skyrocketed, making them status symbols (along with their quality) because people were dying to have something they weren’t allowed to have.
The Window of Opportunity (Then Closing)
In 2014, a glimmer of hope entered when the Obama Administration normalized relations with Cuba. By 2016 regulations had loosened enough that Americans who traveled to Cuba would be able to return home legally with cigars, and rum, so long as it didn’t exceed $100 worth of each item and it was for personal use only (meaning one would be bringing back fewer than $100 value of tobacco products).
Finally, it seemed that after over fifty years of black market shame and operations, Americans could legally come through customs with Cuban cigars in their bags.
This caused a stir in the cigar community. For decades people went without experiencing genuine Cuban tobacco because they couldn’t break the law or were confined by travel restrictions or deemed too much of a risk to bring anything Cuban home. Travel into Havana increased suddenly, with lines outside cigar shops at a time when American tourism had been unheard of for generations.
Unfortunately, this didn’t last.
By 2017 new restrictions entered travel to Cuba and it became an even harder venture for Americans to get there without having every step tracked and needing to have an approved reason for being on the island. Then, in 2020 with further regulations, most links to Cuba were severed again; presently it does not matter if one goes to Cuba and purchases their products legally: one is still prohibited from bringing those items back into the United States.
Where Things Stand (Legally and Illegally)
At present, there’s a legal air, or rather a ban, surrounding Cuban cigars that are incredibly frustrating for cigar lovers nationwide. Under any circumstances, American citizens/residents cannot purchase, import or attempt to bring Cuban cigars into America, even if purchased legally in Canada or Mexico or even Cuba itself.
It’s monitored by the Office of Foreign Assets Control (OFAC), which doesn’t care if you’ve bought 25 cigars to last yourself one year or you’ve bought just one: all cigars are prohibited because OFAC deems anything from any interest connected to Cuba, from tobacco to baseballs, to be problematic for national relations.
Therefore, should you bring Cuban cigars into American borders, it’s purely civil punishable (although criminal punishment is reserved for commercial enterprises, not private collections).
Thus, what many people find confusing is that this does not render anyone with a pre-embargo cigar illegal. Meaning if someone has an ‘original’ stock from Cuba given to them pre-embargo or has Cubans from their trip that allowed them to bring Cubans back with no issue between 2016-2017, and can prove it, there’s no issue possessing them. Enforcement complicates things since people have confiscated cigars because they wouldn’t note when they got them; however, customs agents aren’t sympathetic, they’re just doing their jobs.
Cuban Cigar Debates – Are They Are Aren’t They?
Yet many cigar enthusiasts question additional enforcement aspects “Are Cuban Cigars Illegal?” is one of the top questions googled related to cigars, and the answer is complicated to federal guidelines and how much power officials want to enforce restriction laws at any given time.
But why do these cigars matter so much more than others?
Because Cuban tobacco is known across the world for centuries of cultivation techniques that make anyone jealous – everyone tried to replicate the same quality/taste elsewhere but it never worked out as perfectly as it did in Cuba.
For example, growers in Cuba’s Vuelta Abajo region create an experience that haunts aficionados in dreams, the climate/soil/abilities, that foster something magical from a gardening perspective transforms into spectacularly different burgeoning plants than other regions can muster. When America limited access to this tobacco sector many Dominican/Nicaraguan/Honduran manufacturers tried hard to fill that gap.
And they have, excellently so. Most premium cigars today rival their Cuban brothers/sisters. Quality control has vastly improved in none-Cuban factories while Cuba has faced myriad production declines after years of filled warehouses and supply chain issues for what should be flourishing international enterprises.
But there’s also a mystique, a part forbidden nature, that has people wanting more. Much like when someone tells someone else they can’t do something, the mere fact it’s denoted as ‘boring’ makes it sound ever more attractive, yet there’s also credit due that exposes how incredible cigar making was in Cuban culture that continues today.
The Counterfeit Problem No One Addresses
However, a secondary problem that few discuss is the counterfeit market people fall victim to across the Caribbean/Mexico, even Europe, where tourists buy “authentic” Cuban cigars from vendors pushing extremely low prices on unknown products. Most are fakes filled with floor slop/on floors where people sweep up random scraps from grow sites and repackage without understanding hoops through which competition hoops jump.
Boxes are deceptively appealing (buy for yourself) but bands and seals are poorly constructed compared to genuine Cuba-made goods; collectors are keenly aware of where these differences lie though it’s easy to fool an unknowing buyer.
This complicates life because if someone thinks they’re genuinely smoking a cigar but instead they’re smoking garbage filler crap, and yet critics say cigars from places like Honduras/DR/Nicaragua are better, it’s tough because they’re getting assessed wrongly through smoke no one should even be smoking.
How Modern Day Cigar Culture Evolved Because of Restrictions
Regardless, and whether it’s good or bad, American culture transformed years ago based on these restrictions. Manufacturers in Nicaragua/DR/Honduras created production facilities galore with fields upon which hard-working men like Padron devoted generations – had Cuban cigars had no restrictions they would never have created phenomenal products nation-wide until they had enough tobacco comparison fields/places under construction.
Thus while enthusiasts have become exponentially savvy about where best tobacco comes from cultivated all over since most have traveled widely for World War 2-esque pieces of information since no one wanted a captive audience focused only on heart-broken souls in Cuba, and instead took pride where authors carved their nooks thanks to access, they knew it was more important to limit spending than intercultural investment.
But it’s not sexy and confusing for many enthusiasts what’s true and what’s not.
With regulations changing over the years sparking “town hall”-type forum conversations online with international audiences who’ve either been detained or challenged confuse cigar lovers when they bring their collections home after a trip thinking they’re legal/worth investing when they’re not.
The Uncertain Future Surrounded by Cuban Cigars
Will things change again? Who knows, the relationship between Cuba and America is tenuous at best more often than not, it depends on what’s trending politically at any given moment; ten presidents later since 1962 it’s clear an open door option gave Cubans what they needed during Obama’s administration, but whatever was bad under Bush and what’s even worse now under Biden is mere gossip easy fallen into.
Thus American cigar lovers will continue enjoying fantastic tobacco options from countries all over Central America/The Caribbean, with both eyes paying attention for future information released down the line; the story isn’t over yet, it’s barely even begun, with sixty plus years gone by not settled anytime soon.
