Barry Foy, Kingpin of Gentlemen Smugglers- Interview Series

While just about everyone in the cannabis industry has a noteworthy story about how they were introduced to the plant and the trade, few have a tale as wild as Barry Foy, Co-Founder of Gentlemen Smugglers. It is a story worthy of a Harmony Korine or Judd Apatow movie, involving international smuggling routes from South Carolina to Lebanon (and no, that doesn’t mean Lebanon, Pennsylvania). The saga includes a federal operation led by a former University of South Carolina classmate and has culminated in a licensed cannabis brand that honors the original story.

For a deeper look into this history, mycannabis.com had the pleasure of speaking with Foy himself.

When did you first get involved in cannabis smuggling? Even with its high illegality at the time, what still interested you about the excitement of it all?

Late ’70s. I was young, on the coast, and the water was just part of life. What pulled me in wasn’t just the money, it was the freedom of it. Being out there at night, running boats, figuring things out on the fly. It felt like you were operating outside the system. There was risk, sure, but there was also a sense that you were part of something bigger, something most people didn’t understand. That’s what hooked me. Plus, of course, outrunning the man.

When did the cocaine trade and its resulting violence in Florida become so horrifying that you and your team moved up to South Carolina? From your experience, why was graphic violence so much more prevalent in the cocaine trade than in the marijuana trade?

Florida started changing in the early ’80s. What had been business turned into something else entirely: faster money, harder people, and a lot more violence. You’d hear about shootings in broad daylight, bodies turning up, deals going bad in ways we hadn’t really seen before. That wasn’t the world we came up in.

So we moved north to South Carolina. It was quieter, drew less attention, and was more in line with how we operated. We were running product and having fun, not trying to be part of that chaos.

The difference between cocaine and marijuana was the stakes. Pound for pound, cocaine was worth a lot more. Coke was big money, fast money and it brought a different mindset with it. More pressure, more competition, more people willing to solve problems with violence. With cocaine, things escalated quick. Marijuana was slower, steadier. Weed wasn’t harmless but it didn’t carry that same edge. With weed, most guys were just trying to do business and stay under the radar.

How was the cannabis from Colombia and the “primo weed” of higher quality than the cannabis you were receiving from Jamaica? When did Jamaica become so “hot” that you had to stop purchasing from there?

The Colombian product, especially the “primo”, was just cleaner, stronger, more consistent. It was handled better from start to finish. Jamaican weed had its time, but it got sloppy. Too many hands, too much attention from law enforcement. By the early ’80s, Jamaica got real hot, lots of busts, too many eyes on it and it just wasn’t worth the risk anymore. Colombia was tighter, more organized, and the quality backed it up. Santa Marta Gold was the legendary landrace sativa from the Sierra Nevada de Santa Marta mountain range in Colombia and that’s right where we went.

When did you and your team decide to add Lebanese hashish to your menu? What added risks came from visiting and securing large quantities in such a war-torn country?

That came a little later, early ’80s. We were always looking for something different, something premium. Lebanese hash had a reputation and it lived up to it. But going over there wasn’t like a normal deal. You’re talking about a war zone. Different rules, different kind of danger. It wasn’t just law enforcement, it was militias, politics, things you couldn’t predict. You had to trust people you barely knew, in places where trust didn’t come easy. One of our largest deals came in the middle of the Civil War. We sailed to Beirut and we had both sides, Lebanese Forces and the Lebanese National Movement, pause fighting as we unloaded the boats. That’s because we were paying off both sides.

How did the Reagan administration, Henry McMaster and the federal government eventually catch you and your team members in Operation Jackpot? What were you eventually convicted of?

At that scale, it was only a matter of time. Operation Jackpot brought a lot of attention, and the feds started putting the pieces together with surveillance, informants, following the money. Guys like Henry McMaster were pushing hard on it. Eventually they built a case they could stick. They actually never caught us smuggling, it was all through real estate, tax, etc. Kinda like how they got Al Capone (side note – I was put in Capone’s cell at the Atlanta Penitentiary). I was convicted on federal drug trafficking charges and conspiracy. Ended up doing eleven years for it.

While incarcerated, how did you get so into cooking and being a chef for the inmates? What were your most well reviewed dishes and did you meet any famous inmates while incarcerated? On your LinkedIn page, you mention Sunday brunches and the Gambino family in particular.

You’ve got a lot of time in there, so you either waste it or you build something. I got into the kitchen and found out I was good at it. Cooking gave me structure and honestly, it gave other guys something to look forward to. Sundays we’d do brunch, which was as close as you could get to normal in a place like that.

As for dishes, anything that felt like real food, omelets, baked chicken, stuff with some flavor, people appreciated it. And yeah, you meet all kinds inside. I crossed paths with guys tied to the Gambino crime family and would cook for them FIRST every Sunday, ensuring no one messed with me. In there, everybody’s just doing time, and you learn pretty quick it’s about respect more than anything else.

After being released, what were the most difficult aspects of life and new changes to adjust to? How did you eventually overcome those challenges?

Hardest part was that everything had changed, technology, business, even how people communicated. But the bigger challenge was internal. After years of structure, suddenly having total freedom was overwhelming. You have to rebuild discipline and direction on your own.

Then there’s the reality of starting from scratch. Reputation follows you, and opportunities don’t come easy.

What helped me was staying patient, leaning on my instincts and relationships, and focusing forward instead of backward. Over time, you find your footing again and I focused on food and restaurants.

What inspired you to eventually enter the cannabis industry after such an exciting life of smuggling? How did your previous experience provide you with an added advantage and understanding of business and proper cannabis cultivation?

It all started as a documentary. I was introduced to two media professionals, Kevin Harrison and Thomas Cutler, and we began working together on a film project. While shooting, we kind of looked at each other and said there’s a brand here, one that’s based on my origin story. The name was a no-brainer: GENTLEMEN SMUGGLERS.

It wasn’t about chasing excitement anymore. It was about doing it the right way. I’d already spent years learning the product, what was good, what wasn’t, how it moved, what people wanted. That doesn’t leave you.

So when things started becoming legal, it felt like an opportunity to take all that experience and build something real. I understood quality, supply chains, risk, just from a different side of it. Now it’s about legitimacy, building our brand, and doing it in a way that doesn’t leave people behind like it did before.

How would you describe the process of creating a legal cannabis brand in both Maryland and New York? Did you find the process to be arduous and unnecessary or was it necessarily thorough?

If you work with good people it makes this a whole lot better. Honestly, we love our teams but finding the right partner isn’t easy. Partnership is key in this business because we all know it’s tough and you gotta get through the ups and downs together. Connecting with SunMed in Maryland came together quickly back in 2023. It’s a family run enterprise with one of the largest production greenhouses in the state. In New York, our partner Nanticoke Farms is also a family run operation. They are solid dudes with a deep understanding of the NY market.

What values from the old days of Gentlemen Smugglers are you incorporating into this new era of legal business for the brand? And how do you balance all the requirements to produce such a diverse menu of products?

It is a wild ride staying on top of different regulations for each market and each state. Still, back in the day we liked to have a lot of fun, and we still do. We infused that old school 70s and 80s good time sensibility into every aspect of this brand. From our design aesthetic to our products to our merch and our media presence. When we think about new products, we think about a wide range of people, not something super niche. I used to deliver happiness to the masses, and I still do. An example of this is a new strain I’m working on from back in the day: it’s a really nice Maui x Bruce Banner that packs a punch!

How do you plan on continuing your cannabis reform advocacy work with organizations like Last Prisoner Project? What would be an example of some sweeping criminal justice reforms, similar to the First Step Act of 2018, that the federal government should pass?

I did eleven years for something that’s now sold legally. You don’t forget that and you don’t walk away from it. That’s why groups like Last Prisoner Project matter. They’re getting people out and helping them rebuild. My role is simple: keep telling the truth about what this cost and push attention and resources their way.

As for reform, it needs to be real, not incremental. Automatic release and expungement for every non-violent cannabis offense. If it’s legal now, nobody should still be locked up for it.

Then real access like capital, licenses, ownership for the people and communities that paid the price. And finally, full descheduling. As long as it sits in a gray area, you’ve got people profiting on one side while others still carry the consequences.

Thank you for joining us, Barry! For more information on Gentlemen Smugglers, please visit its website.