Smuggling on the East Coast: Exploring the History


  • to import or export secretly contrary to the law and especially without paying duties imposed by law.

Based on the definition above, when you hear the word ‘smuggling’ – it should undoubtedly evoke scenes of danger, intrigue, history and myth. And rightfully so. Here at Gentlemen Smugglers, we’ve lived ‘the life’ and have survived to tell the real tales; we are thrilled to finally be bringing our unmatched cannabis products and our unparalleled storytelling to the Commonwealth of Massachusetts!

If you have been following along with our previous blogs, we covered the basics of our true story, talked about why we chose to launch in MA, introduced you to one of the main smugglers (Barry “Flash” Foy) and touched on the importance of tides

Let’s now dive further into smuggling lore as we talk about its infamous history on the eastern coast of the United States.


Pirates & Buried Treasure on South Carolina’s Coast

Since the GS crew has deep roots in South Carolina, it’s important to note that historically there is actually another group of smugglers who were also known to haunt the same shores: pirates. These included the infamous Blackbeard, Captain Kidd, and Anne Bonney:

“The [South Carolina] coast, laced with islands and inlets, lent itself to the purposes of pirates and others who sought concealment and secrecy. It was easy to lose pursuers among the sounds and creeks. Little River itself is short, tidal and flows north to the ocean. Off it are Dunn Sound and other tidal creeks which wind around and behind barrier islands.”

In fact, in the above-quoted article about the town of Little River (which actually makes mention of our very own Barry “Flash” Foy & Operation Jackpot) there’s even some intrigue that has to do with everyone’s favorite pirate feature: buried treasure. 

Because Little River, Georgetown, and Conway were often-used Gentlemen Smugglers drop points back in the day — who knows? Perhaps there’s a stray ‘square grouper’ of perfectly aged ‘OG’ GS green somewhere out there to be found amongst the pirate gold. 


Florida Rumrunning During Prohibition 

We would be remiss if we failed to make mention of the ‘rumrunners’ that owned the eastern coast of the U.S. during the days of Prohibition – and specifically the folks that were operating in and around Floridian shores. 

According to the Florida Maritime Museum, these smugglers employed many innovative designs in order to bring much-sought-after liquor to anxiously awaiting would-be imbibers: 

“Rumrunners devised all sorts of schemes to avoid being caught with illegal goods. They falsely labeled cases of liquor and kept them amongst legitimate shipments. They stored the bottles in tanks chained underneath their boats that could be cut loose if they were in danger of being caught. 

False bottoms were devised so that liquor could be hidden underneath legal cargo. If pursued by the Coast Guard, smugglers were known to throw their contraband overboard – either to hide the evidence or to lessen their load in trying to outrun patrols.” 

These cunning men and women, although not the first or the last of their ilk, were surely continuing an American tradition; one that involves the freedom of choice, adventure, and the ever-enticing thrill of the chase…


Gentlemen Smugglers: Continuing an American Tradition

Seemingly picking up where the pirates and rumrunners left off, our rowdy crew of Gentlemen Smugglers employed much of the same techniques in their exploits during cannabis prohibition (to skirt the attention of the long arm of the law, and to ensure the safe delivery of the ganja that was promised to their associates and the good people of the east coast, and beyond).

In an excerpt from Jason Ryan’s New York Times bestseller – Jackpot: High Times, High Seas, and the Sting That Launched the War on Drugs (featured in this 2011 NPR piece) – the art of non-violent smuggling is underscored as being decidedly not for the amateur, and certainly not for the faint-of-heart:  

“The basic business plan for smuggling pot is straightforward. For every deal, a smuggler must coordinate three parts: the purchase, transport, and distribution of marijuana. On paper the tasks seem manageable, so long as a kingpin and his employees possess an adequate amount of moxie. 

But many an amateur smuggler has made a go of bombing in a load only to become bogged down by the inevitable mishaps that occur when inexperienced sailors pack a boat to the bursting point and try to cross the Caribbean. 

When these amateurs stumbled, they called established kingpins in to help, sacrificing a healthy amount of profit to salvage the load. Fortunately for the stumblebums, South Carolina was home to plenty of savvy kingpins, including Columbia natives Barry “Flash” Foy and Les Riley.”

The Gentlemen Smugglers crew and all of their various associates were the ones to go to when it came to quality bud, and for good reason, as the above-quoted passage shows. Now they’re back to do it once again — this time to the Massachusetts legal cannabis market. 


GS Premium Cannabis Flower Products Now Available in Dispensaries Across MA!

Be sure to stay tuned for more blog content & check us out in these fine Massachusetts Dispos:

Cape Ann Cannabis

The Haven Center



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Peter Cardoz

As a passionate cannabis advocate, lifetime food enthusiast and veteran scientist, Peter brings his wealth of knowledge and love for cannabis to the Gentlemen Smugglers team. He started his research career from an early age, eventually conducting research at The Jackson Laboratory for Genomic Medicine, where he become published in Nature Communications.

In 2021, Peter started his own consulting company, Cardoz Blended Gourmet, and a launched a line of gourmet, live resin infused CBD culinary oils.

Cathy O'Hara

Meet Cathy, head of People Operations at Gentlemen Smugglers. Cathy is a former journalist turned Tech Pioneer. As the 35th employee at AirBNB, Cathy helped scale the home-sharing startup into the mega star it is today.

Cathy joins GS with a proven knowledge of recruiting, people leadership, community relationship building, customer service operations, workflow planning and project management. Plus she’s just a cool world traveler.