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Dec 9, 2022
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28 grams of game: The Gentlemen Smugglers

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In 28 grams of game, Leafly breaks down the story of South Carolina’s legendary cannabis smugglers who are now navigating the legal market in Massachusetts.

At 21, Barry Foy made his first million dollars. He was the ringleader of a cannabis smuggling ring that Federal agents dubbed “the gentlemen smugglers,” because they were mostly college-educated “good ole boys” from South Carolina. They went to school with the current governor, Henry McMaster, and led him on a cat and mouse chase for years before he realized his targets were former friends.

After a 15-year run, Foy’s crew was taken down by “the sting that started the War on Drugs,” a joint operation between the IRS, DEA and FBI that landed Foy an 18-year sentence, which he served 11 years of. The story is meticulously told in 2011’s Jackpot, a Wall Street Journal Bestseller by Jason Ryan, and is in production to become a documentary series.

Now 50 years after their first run, Foy is writing the Smugglers’ final act with a new expedition into uncharted waters. His licensed brand Gentlemen Smugglers is now available in Massachusetts dispensaries, with more states to come.

And despite legalization, the stakes are higher than ever. After a lifetime-served on the run or behind bars, and with most of Foy’s fellow smugglers retired or deceased, it’s now or never for the last gentleman standing. Foy is in his 70s, still running a tight ship to ensure the smugglers’ story lives on in proportion to their influence.

For this installment of 28 grams of game, Leafly hit South Carolina’s Edisto River with Foy to see the backwater routes his team once used to move tons without detection. Here’s what we learned along the way.

1. Go with the flow

Barry Foy shares memories of his days on the South Carolina canals that connect in the Atlantic Ocean. (Kevin Harrison)

The unsteady state of the cannabis industry intimidates many investors and operators. But Barry Foy is used to leading unsure voyages with confidence. He’s already moved more wholesale pot than nearly anyone else on the East Coast, and under much rougher conditions than today’s licensed operations. When smuggling, if the boat gets stuck, someone misreads a tide, or it’s the middle of the night and they’ve got the chart wrong,” they could end up lost at sea or in custody.

One of the Gentlemen Smugglers’ first trips to Jamaica included a leak that had the crew shoveling water out of the boat for hours to stay afloat. So while the legal cannabis game is now far more competitive than the isolated canals the smugglers carved through in the 70s and 80s, there’s no comparing the risk tolerance and endurance Foy’s built over the years. Which is why it’s so easy for him to go with the flow as the legal industry ebbs and flows. And it’s no surprise their unofficial motto is #enjoytheride.

2. Teamwork makes the dreamwork

Foy played basketball in college and understands how to lead a team with the control of an elite point guard. As a young smuggler, he shined while leading older peers on potentially life-threatening missions on the open sea.

Decades later, at the peak of COVID-19 uncertainty, Foy recruited a new team of extraordinary gentlemen to paint a modern portrait of the smugglers’ adventures. Since the plant is now legal, Foy knew selling it would be relatively easy. The challenge of today’s weed game is building out a brand that resonates as deeply with smokers worldwide as the smugglers’ journey does in rural communities up and down the East Coast.

Barry Foy (left) and Les Riley (middle) were two of the leaders of the Gentlemen Smugglers. (Gentlemen Smugglers)
Barry Foy (left) and Les Riley (middle) were two of the leaders of the Gentlemen Smugglers. (Gentlemen Smugglers)

To help paint the picture, Foy brought on world-traveler and media-whiz Kevin Harrison along with New York-native Thomas Cutler, a VP at Discovery who helped pioneer the true crime genre. Harrison and Cutler both spent time in Charleston, South Carolina and quickly learned the legend of the Gentlemen Smugglers by word of mouth. They were local legends in a state that still prohibits the plant. And the story felt like a mix of Breaking Bad and Cocaine Cowboys with even more layers and characters to explore.

3. Take them to your leader

From day one to today, the star of the show has always been Barry “Flash” Foy. “Barry’s a leading man,” Cutler explained, drawing on his own storytelling expertise to properly cast and frame the Gentlemen Smugglers’ story for streaming audiences. Cutler compares Foy’s complex charisma to Tony Soprano, who is relatable, even likable, but still capable of dark turns that your average viewer can only imagine.

“I don’t wanna set them up to be like, they’re these perfect guys,” Cutler said over coffee in downtown Charleston. “Everyone has issues, has fallacies, has problems–A good side and bad. But when we first got Barry on camera, I knew he was a star in a second. Just because of the TV background, how quick he was with a turn of phrase,” Cutler explained.

4. Gentlemen finish first

(Kevin Harrison / Gentlemen Smugglers)
Barry Foy (left) tells Leafly East Coast Editor Calvin Stovall about his days smuggling weed along the Carolina coast.(Kevin Harrison / Gentlemen Smugglers)

“Asshole or gentleman? Gentleman sounds a whole lot better to me.”

Barry “Flash” Foy

The smugglers didn’t operate like pot pirates, aside from the questionable hygiene that sometimes arose on long trips. “All these guys went to college, they all knew each other in college, and Barry was very well-traveled and charismatic,” Cutler said. “The stereotypical kingpin is not the kind of person I’d want to hang out with, but Barry was very much the opposite. Because he wasn’t talking about himself. He wasn’t saying, ‘Look what I did.’ This is a passion for him, but it’s also a business.

5. When in doubt, take charge

When they started smuggling, Foy put on his CEO hat and said, ‘I was running a corporation.’ Cutler said it reminds him of Breaking Bad, “but forget the meth and the murder.” It’s all about a man with a plan taking full measures to achieve it, Cutler explained. “And once I got to know the law enforcement side of all the folks that were after them, it’s also like Catch Me If You Can, like what they did to stay one step ahead.”

Gentlemen Smugglers
Les “The Boss” Riley (left) and Barry “Flash” Foy (right) lead a ring of 100 men and women to import 250 tons of cannabis (worth $1 billion) into the U.S. from Jamaica, Colombia, and Lebanon. (Gentlemen Smugglers)

The current team thinks viewers will love the Robinhood morals Foy and the Smugglers operated with. They weren’t violent. If someone crossed them, they would simply X them out of future deals. They were simply too busy for violence. All of their time was spent smoking weed and weighing money piles that were too thick to count by hand.

6. Know the law

Operation Jackpot was the first presidential sting in the Drug War. The Gentlemen Smugglers were the target, and over 100 men and women were eventually sentenced. They were able to evade enforcement for years because of the sophisticated maze of waterways that line the Carolina coast.

As natives, Foy, Les Riley, and Bob Meyers knew exactly how to stay ahead of the coast guards and local authorities. It took a historic first-time collaboration between multiple federal agencies to connect the dots that landed the smugglers behind bars. Operation Jackpot wasn’t just the Drug War’s first major sting. It was also the first time the FBI, IRS, and DEA worked in unison.

7. Keep your enemies close

South Carolina Gov. Henry McMaster led the investigation against the smugglers. As Reagan’s United States attorney choice, McMaster chased the Gentlemen Smugglers for years without realizing he knew them personally. “We had a lot of marijuana and hashish, and we didn’t know who was bringing it in,” McMaster said in the sizzle reel for the Gentlemen Smugglers docu-series.

Henry McMaster, current South Carolina Governor and former U.S. Attorney, chased the Gentlemen Smugglers up and down the East Coast for years. (Gentlemen Smugglers)
Henry McMaster, current South Carolina Governor and former U.S. Attorney, chased the Gentlemen Smugglers up and down the East Coast for years. (Gentlemen Smugglers)

“President Reagan gave me a green light to innovate and do things that had not been done before.” Gov. McMaster said the plan was to “go find people spending more money than they could possibly be making.”

8. Know the stakes

When the smugglers were making runs, they were fully aware of the potential consequences. With each trip, they raised the stakes, venturing to the middle eastern nation of Lebanon during a Civil War to export hashish for their operation. Foy and the smugglers paid the ultimate price when the authorities finally caught up to them.

For all of the eighths of weed he snuck into the states, Barry served about one-eighth of his life behind bars, living a Shawshank Redemption-esque existence.

9. Play the political game

On the inside, he had the protection of Italian mobsters. They took a liking to him while he worked in the kitchen. Foy used his keen people skills to identify the keys to winning friends and influencing people. While working in the kitchen, he made sure the Italians got served the best food, and first. He also smuggled olive oil and other highly-valued contraband with the help of prison workers. The risks paid off, helping him survive his time with his peace of mind. Today, the stakes are set by father time, with Foy, Cutler, and company pushing to cement the Gentlemen Smugglers’ legacy through quality content and legal cannabis products.

“30, 40 years ago the stakes were jail, plain and simple: You get caught, you go to jail, which they did. I think the stakes now are more on the business side. I mean, truly all of us are involved in the business side. Barry, Willie, Tammy, Skip, the whole team, there’s an element of legacy of telling their story on the, there’s certainly an aspect of entertainment because it’s fascinating. It’s riveting.”

Thomas Cutler, VP Warner Bros. Discovery, Co-Producer of Gentlemen Smugglers docu-series

10. Protect your legacy

(Kevin Harrison)

With his former smuggling partner Les preferring to stay behind the scenes, and their third partner Bob Meyers passing away behind bars, Barry is carrying the torch for one of the East Coast’s richest legacy cannabis operations. And he’s still running a tight ship to this day, overseeing each element of the cannabis and content projects to make sure they live up to the standard he and the smugglers set.

11. Use your network wisely

The Gentlemen Smugglers weren’t above using their state’s “good ole boys” network to enable their smuggling. For one of their first trips to Jamaica, Barry went through a lawyer friend to get a corrupt local judge to vouch for them when they needed a reference to buy the boat. “Them boys are fine, go ahead and give them that boat,” the judge said over the phone.

12. Follow the money

The smugglers were so good at evading law enforcement that it took financial records to prove what they were doing in court. McMaster used a “net worth” approach to identify criminals by comparing the cost of their homes and assets with their stated income.

The strategy brought the Internal Revenue Service, US Customs, The Drug Enforcement Agency, and the Federal Bureau of Investigation into the fold. At the time, it was unprecedented for the agencies to share information or work in concert. They were also limited by 1970s surveillance, which was incapable of tracking the countless miles of coastline curled along the state’s eastern seaboard. 

13. More attention, more problems

If not for their flashiness, the Smugglers may have evaded authorities even longer, if not forever. Today, Foy operates with modest flair, pushing a foreign-built luxury car, but dressing in t-shirts, hoodies, and jeans that show he’s ready to set sail at any given time.

“It was virtually impossible to catch them in the act. We decided to figure out who they were and catch them at home.”

Gov. Henry McMaster, former U.S. Attorney and current South Carolina governor who built the case that put the Gentlemen Smugglers behind bars.

14. Give the people what they want

To grow awareness in Massachusetts, Barry and the Gentlemen Smugglers team are working the dispensary circuit with in-person visits. Most shoppers are unaware that the weed that once flooded Boston’s streets originated in Foy’s small cargo boats. But they’re always charmed to learn that the cool gray-haired fellow before them is perhaps the East Coast’s most legendary legacy provider.

15. Ladies first

Barry and the gang didn’t choose the name Gentlemen Smugglers, law enforcement did. And Foy still feels it’s a disservice to the women who were essential to the original operation. Women like Miami Tammy, aka the Queen of the Kingpins, and Captain Judy left a mark that Foy, Cutler and company cherish to this day. And they still play key roles in helping develop the brand and products for the legal market.

16. Take nothing for granted

Barry is still blown away every time he visits a dispensary in Massachusetts. As someone who put so much effort into getting the plan to people when it was illegal, it’s still shocking to see people buy and consume so freely. “People take weed for granted now, but there were huge stakes at the time,” Cutler said. “And there still are in certain places, South Carolina being one. You run a pretty serious risk there.”

17. Follow your passion

Barry Foy and company smuggled weed into America because they had a passion for the plant. As Foy’s co-producer on the Gentlemen Smugglers documentary, Warner Bros. Discovery VP Thomas Cutler is knee-deep in his favorite genre: True crime. “I had always been looking for a project that really spoke to me. And one that was a true authentic story. In the world of true crime, I’ve done so many true crime shows. I’m an avid true crime reader and, and I’ve just always been fascinated by that world.”

18. Work with what you’ve got

Barry Foy gives smuggling tips. (Kevin Harrison)
Barry Foy gives smuggling tips from the deck of one of his favorite boats. (Kevin Harrison)

Cutler joined the documentary project during the first wave of COVID. They couldn’t run a regular production, but they turned the unfortunate circumstance into an advantage.

“It’s South Carolina, so we could do the whole thing outside. And because the story is such an outside story, um, it really lent itself to it. So every single meeting we had about it was they were all outside, you know, 30 feet apart, yelling at each other,” Cutler said.

19. Recognize the struggle

Foy is fully aware of the advantages he and his fellow smugglers had over others. And now that the plant is legal, he supports states like Massachusetts that are looking for ways to pay social equity to legacy operators. Foy was the rare member of his crew brave enough to venture to Miami and Jamaica, forging connections authentically with locals and gaining their trust with ease.

While on an early trip to Jamaica to load up, Foy and co-pilot Ray Brunson became hypnotized by the waves. They recognized the poetry in Ernest Hemingway’s description of the Caribbean sea as a metaphor for the struggle between American prosperity and Caribbean poverty. With every successful trip, Foy and the gang got closer to the former. And Foy still holds other legacy operators in high regards, knowing first hand the risks they took.

20. Confidence is key

Barry’s surviving running mates are still in awe of the confidence he had back then, and today.

He learned that nice guys finish last in the smuggling business, and often muscled himself into any deal he wanted in on. And he didn’t just take a cut, he wanted the lion’s share. “If you got 1000 pounds, Barry’s getting 600 you’re getting 400,” said one smuggler in Jackpot. Barry wasn’t a malicious leader. He was tall and athletic, with curly hair and an ego and swagger that were hard to argue with. “He was destined to be huge,” wrote Jason Ryan in Jackpot. “There was nothing else Barry could do.”

21. Don’t be afraid to go backwards

“I’m one of the few guys that ever taken pot back to Jamaica,” Barry said, remembering an early trip that was compromised by a shaky boat. Instead of risking jail or capsizing, They stopped on a nearby island and turned around.

The legal cannabis industry requires similar patience, as does the documentary production. With weed prices up and down, Foy and the Gentlemen Smugglers are focused on giving customers a memorable experience that can be scaled as more states legalize. But to claim their stake of the industry, they must first relive their past escapades in a way that captivates viewers who weren’t even born during Operation Jackpot.

22. Balance the tide

The Gentlemen’s approach includes products that simplify the experience for the East Coast’s less seasoned smokers. Their staple offerings include a “High Tide” sativa-leaning flower for daytime use along with a “Low Tide” indica-leaning cultivar intended for nighttime use. Many of the customers are Foy’s age, uninterested in high-THC counts and exotic flavors. To balance the market’s infatuation with sweet dessert strains, the Gentlemen Smugglers are giving more accessible options for the OGs.

23. Stay busy

As a kid, Foy always had a job. He would deliver newspapers and groceries with boundless energy, then graduated to pumping gas and ganja. Now, past 70 years of age, Foy still has the energy of a rockstar when he headlines dispensary appearances across Massachusetts.

24. Quality is key

At one point in their smuggling days, Foy and Riley had to move on from their Jamaican connection. They found better price and quality in Colombia, so they linked up with Bob “The Boss” Meyers and expanded their operation. And they didn’t stop there.

25. Go the extra mile

A trunkful of hashish from Lebanon. (Gentlemen Smugglers)
A trunk full of hashish from Lebanon. (Gentlemen Smugglers)

When the Gentlemen Smugglers wanted to add premium hashish to their supply chain, they went directly to the source. During a civil war, they travelled to Lebanon, they paid both sides to let them safely export the goods. Getting them back in America via the countless waterways of South Carolina was a cakewalk in comparison to the study abroad mission, which you can read more about in Jason Ryan’s Jackpot.

26. No coke, no guns

The Gentlemen Smugglers never felt like what they were doing was criminal, and they kept a clear conscious by following two rules: No guns and no smuggling cocaine. They knew guns invited violence. As did the white powder. So even though coke was more lucrative, it wasn’t worth toting an automatic weapon and risking war with pirates and cartels.

27. Take your time

The term green rush inspires a level of urgency in most cannabis operators. No one wants to look back in two decades and feel like they missed their chance to create generational wealth through legal weed. But The Gentlemen Smugglers are not rushing any steps of this process. This is likely their only chance to cash in on the legal industry they helped build from scratch. So they’d rather take their time and get it right than rush into things just to say they gave it a shot.

28. Give it your all

Speaking to Barry Foy, you get the impression he’s lived a life of few regrets. You wouldn’t know he served over ten years in prison unless he told you. But once he does, it makes all the sense in the world, given his unflappable demeanor and people skills. As we cruised along the shore, watching dolphins trap fish against the bank, and marveling at how easy it still might be to sneak contraband along the Edisto River, Barry captained the ship with the same calm confidence that made him the lead smuggler five decades ago.

Whether the industry recognizes it now or 100 years from now, Foy and the smugglers will live forever as godfathers of East Coast cannabis. But you don’t have to worry about giving them their flowers. Just buy some of their legal flower for yourself and tell a friend about the South Carolina boys who survived the front lines of the Drug War and lived to tell their story.

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