S4|E26: Once Smugglers | Part 1

Summary

Gone South: S4|E26 - Once Smugglers | Part 1 Release Date: April 9, 2025
Host: Jed Lipinski
Produced by: Audacy Podcasts

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Introduction

In the twenty-sixth episode of the fourth season, "Once Smugglers | Part 1," Gone South delves into the intricate world of drug smuggling in the southern United States, focusing on the lives of Dickie Lynn and Rico DeShaw. Set against the backdrop of the 1970s and 1980s Florida Keys, the episode explores how these two friends transitioned from modest beginnings to becoming key players in the burgeoning marijuana and cocaine trade.

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The Tragic Beginning

The narrative kicks off in late September 1987 with a harrowing event that sets the stage for Dickie Lynn's deeper involvement in drug trafficking.

• Dickie’s First Encounter with Tragedy:

  [02:54] Jake Brennan: "I was laying down on the Runway. It was still hot... I could hear it squawking... And then there's a huge fireball at the end of the Runway..."

Dickie, a seasoned drug trafficker, witnesses the fatal crash of a plane carrying cocaine, marking the beginning of his deeper plunge into the illicit trade.

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Early Life and Formative Years

Jed Lipinski paints a vivid picture of Dickie and Rico's upbringing in Islamorada, Florida, highlighting their strong ties to the water and the fishing industry.

• Dickie’s Youth:

  [06:11] Jake Brennan: "We were always out in the boat, always diving, always fishing... I thought I was, you know, I was rich."

Growing up on Isla Morada, Dickie's early life was steeped in fishing and community activities, fostering skills that would later prove invaluable in smuggling operations.

• Rico’s Background:

  [07:28] Rico DeShaw: "We would jump on sea turtles and ride them around... Navigating a boat at night... very, very comfortable."

Rico, Dickie's best friend, shared a similar passion for marine activities, which would later translate into their smuggling expertise.

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Catalyst for Change: The Loss of a Father

The turning point comes in 1972 when Dickie's father dies in a car accident, leading Dickie to drop out of high school and enter the workforce to support his family.

• Dickie’s Struggle:

  [08:35] Rico DeShaw: "I didn't know where to go... My father just got killed in a car wreck."

This personal tragedy propels Dickie into manual labor, leaving him dissatisfied with his earnings and seeking alternative income sources.

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Entry into Drug Smuggling

An invitation from an associate introduces Dickie to the lucrative but dangerous world of marijuana smuggling.

• First Smuggling Job:

  [10:24] Jake Brennan: "We'd get another boat on its way... every couple weeks we would do a trip."

Despite having no prior experience with drugs, the promise of substantial money lures Dickie into leading smuggling operations, transporting marijuana from secluded stash houses to Miami.

• Initial Success and Temptation:

  [12:16] Jake Brennan: "The more they'd want to do... I could say I was ruined."

The financial gains are immediate, with Dickie receiving $35,000 after his first successful run, igniting his ambition to continue and expand his operations.

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Rico DeShaw’s Involvement

Rico returns to Islamorada after his short-lived NFL career, facing financial struggles, which makes him susceptible to Dickie’s enticing offer.

• Rico’s Introduction to Smuggling:

  [19:54] Rico DeShaw: "I need some guidance here... that's the beginning of it."

Encouraged by his mother’s tales of his bootlegger grandfather and the allure of easy money, Rico joins Dickie, transitioning from a substitute teacher to a high-earning smuggler.

• Formation of Partnership:

  [20:55] Rico DeShaw: "Why don't we do it for ourselves?"

Together, Dickie and Rico establish their own smuggling network, leveraging their intimate knowledge of the Florida Keys to navigate and execute their operations efficiently.

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Operational Expansion and Tactical Innovations

As their smuggling business grows, Dickie and Rico develop sophisticated methods to evade law enforcement and maximize profits.

• Enhanced Smuggling Techniques:

  [28:05] Rico DeShaw: "Their handle was angel, because he was our Angel."

They innovate by utilizing disguised vehicles, such as school buses marked with local schools' insignia, to transport larger quantities of drugs without attracting suspicion.

• Collaboration with Law Enforcement:

  [26:40] Rico DeShaw: "Sometimes we have some stuff left over and we need somebody to handle it."

This unexpected alliance with certain law enforcement officials provides them with a unique level of protection, allowing their operations to flourish under a veil of legitimacy.

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Transition to Cocaine Smuggling

The escalating presence of the Coast Guard and heightened federal scrutiny shift the market dynamics, steering Dickie and Rico towards cocaine, which offers higher profits with less bulk.

• Shift to Cocaine:

  [31:52] Rico DeShaw: "The cocaine, you really up the odds with the money."

Cocaine’s higher value-to-weight ratio makes it an attractive alternative, despite its increased risks and the violent reputation of its primary suppliers, such as Pablo Escobar.

• Relationship with Pablo Escobar:

  [33:48] Jake Brennan: "He was great... he was a good man."

Dickie recounts his interactions with Escobar, portraying him as punctual and reliable, despite the cartel's notorious brutality.

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Innovative Smuggling Strategies

To adapt to tighter law enforcement controls, Dickie and Rico devise creative smuggling methods, such as using airplanes and strategic drop sites.

• Flying over Smuggling Operations:

  [34:01] Jed Lipinski: "He was a good man... but he had a pretty bad reputation down in Colombia."

Rico takes to the skies, piloting aircraft to transport cocaine from Colombia to remote drop sites, minimizing the risk of maritime interceptions.

• Clever Disguises and Transportation:

  [28:05] Rico DeShaw: "We had this conversation, said, well, why don't we do it for ourselves?"

Their use of legitimate aviation work as a cover story not only provides transportation but also serves as a credible alibi for their movements.

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The Illusion of Invincibility

As the duo's wealth and influence grow, so does their sense of untouchability, leading to reckless behavior and inflated egos.

• Living the High Life:

  [30:02] Jake Brennan: "It was so easy for us to do it."

Unlike their high-profile counterparts, Dickie and Rico maintain a low profile, enjoying their wealth without the ostentatious displays that often attract unwanted attention.

• Personal Indulgences:

  [35:02] Rico DeShaw: "I would land a Hughes 500D in the parking lot and pick somebody up."

Their newfound wealth allows them to indulge in luxuries, from expensive cars to private jets, further distancing themselves from their humble beginnings.

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Conclusion and Foreshadowing

As Dickie and Rico navigate the treacherous waters of drug smuggling, their operations thrive due to strategic alliances and innovative tactics. However, the increasing pressure from federal agencies and the inherent dangers of their trade hint at impending challenges.

[35:35] Jake Brennan: "That's how you get..."

The episode concludes with a sense of looming tension, setting the stage for the next installment where the consequences of their actions begin to unfold.

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Notable Quotes

• Dickie on First Realization of Consequences:

  [15:59] Jake Brennan: "I'll stop when I make a million. And you can't stop because the greed takes over."

• Rico Reflecting on Operation Growth:

  [21:17] Rico DeShaw: "We realized we were making a lot of money for a lot of other people because they were using our expertise on the water."

• Dickie on Feeling Untouchable:

  [35:18] Jake Brennan: "We had a lot of toys and did what we wanted to do... bulletproof and they can't touch me."

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Key Takeaways

• Community Roots and Skill Transfer: Dickie and Rico's deep connection to the Florida Keys and their maritime skills were pivotal in establishing a successful smuggling network.

• Adaptation and Innovation: Facing increased law enforcement scrutiny, they adeptly shifted their operations from marijuana to cocaine, utilizing aviation and strategic disguises to stay ahead.

• The Seduction of Wealth: The substantial financial rewards from drug smuggling fostered a sense of invincibility, leading to riskier endeavors and a gradual moral descent.

• Complex Relationships with Law Enforcement: Their unique relationship with certain law enforcement officials provided both protection and a potential pathway to further entanglement with authorities.

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Looking Forward

"Once Smugglers | Part 1" sets the foundation for exploring the rise and eventual challenges faced by Dickie Lynn and Rico DeShaw in the drug smuggling underworld. The next part promises to unravel the consequences of their empire-building and the inevitable clash with larger criminal entities and federal agencies.

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For More Information: If you have any information, story tips, or feedback, please reach out to the Gone South team at gonesouthpodcastmail.com. Follow us on Facebook, TikTok, and Instagram @GONE SOUTHPodcast for bonus content and updates.

Transcript

[Jed Lipinski]

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[Jake Brennan]

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[Jed Lipinski]

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[Jake Brennan]

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[Jed Lipinski]

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[Jake Brennan]

I was laying down on the Runway. It was still hot. The asphalt was still hot from the daytime. And I'm looking up at the stars. It was a beautiful night. I had a radio. I had it just sitting on the asphalt, sitting beside my head, and I could hear it squawking, you know? And I said, that's him. He's coming. And I called him on the radio, and I said, hey, how you doing? He goes, great, man. Everything went well. I said, how's little bro doing? He goes, he did? Wonderful, great. I said, okay. I said, well, we're here, buddy. Just come on home, you know?

[Jed Lipinski]

Dickie was a drug trafficker. He'd had pot and cocaine flown into this airstrip many times before, and it had always gone off without a hitch. As he waited for the plane to come in, he got a call from an associate at the far end of the Runway.

[Jake Brennan]

And he calls me up, and he said, hey, some fog just came up off the river. And I said, well, how bad is it? And he goes, it's not too bad. It's just. It's pretty thick, but it's not too bad.

[Jed Lipinski]

Dickie called the pilot on the radio to tell him about the fog. But he was an experienced flyer. He didn't seem too concerned.

[Jake Brennan]

He says, oh. He said, I got you, brother. He said, I see you. No problem. I'll see you in a minute. No more talking. See you. And so I hear him put it into a hard turn. When the plane's coming at you, you can't hear it. You know, you can hear him going away, but you can't hear him coming at you. The only thing we'd hear is, like, when he'd land. And so I'm sitting there waiting to hear the tires hit the pavement. And bo. I mean, first there was a loud crack, and then there's a huge fireball at the end of the Runway. And so we're like, oh, shit. So we drive down there, and he had hit a pine tree coming in on final. And the pine tree, basically, when he hit it, it just slammed him right down into the perimeter road. And he was thrown out of the plane because he didn't. I'm sure he didn't have a seatbelt on because he was such a hot dog. He was such a good pilot. And his brother was still strapped in the plane, but they were both dead. And we basically just spun the truck around and left you know, we figured the police would be there any minute, and so we all went. And I went to New Orleans and flew back to Colorado. And, yeah, that was basically the one that started the ball rolling on everything with me.

[Jed Lipinski]

I'm Jed Lipinski. This is gone south. As far back as he can remember, Dickey Lynn lived on the water. He grew up Isla Morada, a small string of islands in the Florida Keys just a short drive past Key Largo. His father ran a small dockside business that sold smoked fish to customers in restaurants. By the time Dickey was 12, he was catching most of the fish they sold.

[Jake Brennan]

You know, we were always out in the boat, always diving, always fishing. Spearfishing was my big thing back then. People would come, and I was about 12 years old at the time, and people would come and they would be like, well, is there anybody we can hire to take us fishing? And they would, oh, go get Dickie. So I would take them and take them down the creek. And of course, I had my spots. I'd take them to the spots, and back then there was plenty of fish. They would catch a bunch of snapper and give me $20. And I thought I was, you know, I was rich.

[Jed Lipinski]

Dickey's best friend was a guy named Rico DeShaw. Ricko shared Dickey's passion for life on the water.

[Rico DeShaw]

I remember when I was small, I had a little boat and we couldn't afford a motor, but I just had a stick. I would push it and I could go out on my little skiff. You know, out there's an island called Dove Key, right out from where our house was. You never saw another boat ever. We spent so much time on the water, we would go shrimping at night and we would do these things. I mean, we did things that people were like, you know, don't quite believe. We would jump on sea turtles and ride them around, you know, go catch lobsters at night because they crawl around at night. We would do all these things at night to where we were very, very comfortable. Navigating a boat at night, which is not an easy thing to do without any kind of navigational equipment.

[Jed Lipinski]

Today, Islamorada's coast is packed with luxury resorts and $10 million homes. The traffic on US Highway 1, the narrow two lane road stretching from mainland Florida to Key west, often grinds to a halt, bottlenecked by tourists and construction. But back in the 60s and 70s, Islamorada was a sleepy, working class fishing village lined with seafood shacks, bait shops and roadside motels. Miami, an hour and a Half to the north seemed like a foreign country. In high school, Ricko and Dickie both played for the football team. They both owned hot rods and spent the summers catching tropical fish for the local aquarium. It was a blissful place to grow up. But in 1972, as they were entering their senior year, tragedy struck.

[Jake Brennan]

And my father was coming home from Miami and he was on the stretch, and the 18 mile stretch used to be very dangerous because it was two lane. You had a lot of people coming from the Keys that were drinking and, you know, so somebody crossed the line and head on with my father and killed him.

[Jed Lipinski]

Later that day, Ricko's father called to say that Dickie was hanging out in their driveway.

[Rico DeShaw]

I said, well, what's wrong? He said, I don't know, something's wrong. I came home, I was somewhere and I came, walked up to him and he had this very unusual look on his face. And I said, dickie, what's wrong? He says, my father just got killed in a car wreck. And he says, I didn't know where to go.

[Jed Lipinski]

In the wake of his father's death, Dickey dropped out of high school and started working construction to help support his mom. Ricko, meanwhile, went off to the University of Miami, where he'd gotten a full scholarship to play football. A few years drifted by, Dickey found himself pouring concrete and pounding nails all day, making $4 an hour. One afternoon, he got an unexpected visit from a friend who we'll call Mike.

[Jake Brennan]

He said, hey, my dad wants you to work with us. And so I knew his father was into. He had his hand in a lot of different things. He was, there's a game called bolita, and it's like a. It's a Cuban lottery. And he would run bolita from Miami to Key West. And he also was involved in cockfighting. So I said, well, what's your father want me for? And he goes, well, he knows, you know, the back country pretty well. And he says, we've got some boats we'd like to bring in. And I said, well, boats for what? You know. And he was like, well, they got pot on them.

[Jed Lipinski]

Dickey had never smoked pot before, let alone sold or smuggled it.

[Jake Brennan]

And I'm, oh, no, I don't think so. I'm not, you know, I'm not. I'm not going to do that. And he's well, you know, before you say no, it's. It's a lot of money. You're going to make a lot of money. And I'm like, well, how much? And he goes, well, I don't know, maybe 10, 15,000. I don't know, he says, but you're going to make more money and you're making work in construction. And he said, all you got to do is lead the boat in.

[Jed Lipinski]

In the early 70s, pot smuggling was fast becoming a booming business in South Florida. Smugglers were ferrying in thousands of pounds of pot from Jamaica and Colombia on speedboats and shrimp trawlers of all the islands in the Keys. Key west, which had been a hub for rum running during prohibition, was the center of operations. But the DEA and US Customs had gradually ramped up their presence there, seizing shipments and tightening control of its busy port and airstrips. In 1975, the feds launched a major sting operation targeting Key west drug traffickers known as Operation Conk, a word that describes both the large sea snail with the spiral shell and a native born Key west resident. The operation took down Key West's fire chief and the city attorney, among many others. High profile busts like that forced smugglers to look for quieter, less patrolled waters. Islamorada, with its hidden inlets and low key marinas, was a perfect spot. And Dickie, who knew those inlets better than anyone, was the perfect guide. After thinking it over for a few days, he decided to give it a try. He called Mike and said, I'm in.

[Jake Brennan]

I had a boat that I had worked all summer long redoing it, and I take my boat and I'd go out in the backcountry and I'd meet this big 52 foot, 55 foot Monroe Hull, had pots stacked all the way up over it with tarps over it. And I would lead it all the way into this house we had. It was a safe house and we, we would offload it and stash it in this house, and we had the caretaker paid off.

[Jed Lipinski]

Once the pot was safely stashed in the house, a group of guys would show up in motorhomes. Dickey would help them load the pot, bale by bale into the vehicles, at which point they'd head to Miami and Dickey's job was done.

[Jake Brennan]

So I started doing that. And then after we did that first load, Mike came to me and he gave me a brown paper bag and it had $35,000 in it. And I was like, wow, you know, I guess you could say I was ruined.

[Jed Lipinski]

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[Courtney Harrell]

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[Jed Lipinski]

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[Courtney Harrell]

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[Jake Brennan]

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[Jed Lipinski]

When Dicky Lynn decided to start smuggling marijuana, he didn't immediately tell wife she was working as a waitress and he wasn't sure how she'd react. He stuffed the first $35,000 he'd earned into a Ziploc bag and hid it inside a wall in his apartment. But the trips continued.

[Jake Brennan]

The more we'd do, the more they'd want to do. You know, it was like every time you'd have a successful trip, the next thing it was like we got another boat on its way. And so every couple weeks we would do a trip.

[Jed Lipinski]

At a certain point, Dickie couldn't hide it anymore. He decided to come clean.

[Jake Brennan]

And so after I got probably $150,000 saved up, I unbundled it all. I put it all on the bed and put the comforter over it. And when she came home from work, I threw her on the bed and, you know, pulled the comforter back, and she's like, oh, my God. She started crying, what have you done? You know? And I was like, well, I'm smuggling pot. And you know, oh, you gotta stop. And I said, well, I'll stop when I make 250. Okay, you'll stop when you make 250? And I said, yeah. And then, okay, you'll stop when you make 500. Okay, you'll stop when you make a million. And you can't stop because the greed takes over. And it's easy. It was so easy.

[Jed Lipinski]

Despite his new source of income, Dickey continued to work construction and live a modest lifestyle. Everyone in tight knit Islamorada knew he was smuggling marijuana, he said, but it wasn't that big a deal. For one, everybody around him smoked pot, and increasingly other locals were starting to get in on the action. As the smuggling trade grew, so did the number of interdictions off the coast of the Keys. When smugglers realized the Coast Guard was closing in, they'd often dump their cargo overboard, leaving bales of marijuana bobbing in the surface. The site became so common, it earned a nickname, Square grouper. At the time, customs and Coast Guard officers used encrypted marine radios to communicate. Anyone onshore with a police scanner or a well tuned CB radio could easily listen in and learn. For example, if a vessel full of pot had just been intercepted, word traveled fast. As soon as fishermen in Islamorada caught wind of a drop, they'd race to the spot, hoping to catch some square grouper of their own.

[Jake Brennan]

Oh, yeah, they would go out. It'd be like Indianapolis 500 going through the bridges. Guys would be going wide open through the bridges trying to get out there first. And sometimes the police were out there, sometimes they were picking them up. But a lot of times, if the Coast Guard would pick them up and a friend of theirs would pull up beside him in the boat and they'd throw some to him.

[Jed Lipinski]

It was around this time that Dickie's pal Rico de Shah returned to Islamorada in his junior and senior year of college. Ricco had started as a tight end for the Miami Hurricanes. He was signed by the Tampa Bay Buccaneers. But a back injury curtailed his NFL career after only a year.

[Rico DeShaw]

And so I came back to my home and I was the assistant football coach here, and I was teaching. I was a substitute teacher. You know, my contract was tied up in what they call arbitration for my injury. So I was kind of broke and I was working as much as I could, but I was living downstairs at my parents house.

[Jed Lipinski]

Like Dickey, Ricko had never smoked pot or associated with drugs at all. But Dickey knew his friend was struggling. He asked his associate to make Ricko an offer.

[Rico DeShaw]

A guy came to my house who I knew and asked me if I'd go out to the end of our channel and guide a boat that was coming in. It was a commercial boat at night. I said to this individual, why doesn't the person come down in the daytime? Why do I have to go out and meet this guy and bring him in the channel? This individual came back and said, well, the boat's full of marijuana. And I said, I'm not going to do that. And he put $25,000 rolled up in $5,000 bundles in a paper bag on my pillow. He said, you just have to go out in your skiff, put a light in your. In the behind your boat, what's called a splash. Well, he's going to follow you in and then you have to lead him back out. And I said, I don't have to meet anybody. I don't have to touch anything. And he goes, no. And he said, if you do it, there's $25,000 more for you.

[Jed Lipinski]

After the man left, Ricko took the brick of cash into the kitchen where his mom was making breakfast. When she saw the money, she shrieked.

[Rico DeShaw]

She said, you've robbed a bank. And I said, no. And I told her the whole story. And I said, I need some guidance here. I'm kind of confused. And then she got to tell me about my grandfather that I didn't know. And he was a bootlegger. And I'm listening to her and she says, they're gonna legalize this anyway. She says, if I was you, I'd make a little bit of money and go on with your life. And she said, do you need any help. And that kind of was the beginning of it.

[Jed Lipinski]

Rico soon became a key member of the smuggling operation Dickey was a part of. He went from making $9,000 a year as a substitute teacher to a quarter million a year as a part time drug smuggler. But the men at the top of the operation were making many times that. Eventually, Ricko and Dickey decided to go out on their own.

[Rico DeShaw]

We realized we were making a lot of money for a lot of other people because they were using our expertise on the water and our skills to locate and find these boats. You know, you try to find a shrimp boat out in the middle of the ocean in the middle of the night, you know, it's not that easy a thing to do sometimes, but we became pretty good at it. And finally we had this conversation, said, well, why don't we do it for ourselves?

[Jed Lipinski]

The two friends approached one of the higher ups who controlled the loads coming in from Columbia. He respected their skills on the water and agreed to go into business with them. Ricko and Dickey quickly developed their own system, leading the boats in unloading them in a local stash house and transporting the product in vans, motorhomes, and the occasional dump truck to a network of farms in Homestead, Florida, a rural area 30 miles south of Miami. At that point, another group took over.

[Rico DeShaw]

And that's where we distribute it to the United States. So Dickie and I, our role, what we got paid for was basically transportation from the shrimper to Homestead. After that, our job was over.

[Jed Lipinski]

As their operation expanded, so did their need for protection. Once, while moving a load into a stash house in the middle of the night, an alarm went off in the house next door. Ricko and his crew dashed inside just before a cop showed up. The whole thing spooked him.

[Rico DeShaw]

I had a friend, and he was a sergeant in the county, and I went to him and I said, I've been doing this, I'm gonna be very honest with you, and I need some help. And he said, how much help you need? I said, I don't want anybody coming up on us in the middle of the night in a police car. He goes, I got it. Next thing you know, Marine patrol comes to us and wants to, hey, you know, we went in on this. So now we had not only onshore police officers, but on the water. And then we had a guy in the coast guard say, yeah, I went in on this. So now we had coast guard commander, the head of marine patrol, and a sergeant in Monroe County. So we were like, this is a blast.

[Jed Lipinski]

Ricko and Dickey's ties to local law enforcement all but ensured their operation ran smoothly in the Keys. But it wasn't long before they caught the attention of a much bigger player, someone with political connections who would take their operation to the next level.

[Jake Brennan]

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[Jed Lipinski]

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[Jake Brennan]

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[Jed Lipinski]

At the same time that Ricko and Dickey were refining their drug smuggling operation, Ricko was pursuing a lifelong goal learning how to fly airplanes. Rico's dad was an airline captain, and Ricko had always planned to follow in his footsteps. But his back injury from the NFL had prevented him from enrolling in the Air Force. So he used the money he earned smuggling pot to pay for flight school.

[Rico DeShaw]

Studied really hard, did all the schools, and I obtained my airline transport pilot rating, which is the highest rating that you could possibly get.

[Jed Lipinski]

When he wasn't unloading shrimping trawlers full of marijuana at 3am Ricca was flying charter planes for companies like Hopajet and Associated Air. Being a pilot provided a convenient cover story, but it also benefited their drug business. By the late 70s, it was getting more and more risky to send loads of marijuana from Colombia to the Keys by boat. So Ricko began flying it over instead, packing a twin engine Cessna with 1500 pounds of pot and dropping it at a designated site in the Everglades. One day, Ricko was at home when he got a call from his mother. A customs agent had just rented the house next door. She said and he wanted to talk to Ricko.

[Rico DeShaw]

And I went, came home and, you know, I walked over and I said, hi, how you doing? He said, hi, how are you? And he said, sit down. I go, okay. So we're sitting there talking, and he was the head of customs for the southeast part of the United States. And he starts in with a conversation, you know, something about, I know you fly airplanes. He said, you ever have any trouble coming through customs? And I said, not really, you know. And he goes, well, he said, I can make sure that doesn't happen. I kind of said, pull your shirt up. He looked at me and said, excuse me. I said, pull your shirt up. And this is the head of customs. So he pulled his shirt up. He goes, you pull yours up. I said, I'm gonna take mine off. I said, I'm not gonna be one of your snitches. You can go to hell. I'm not going to do it. He said, I'm not asking that. I said, what do you want from me? He says, well, sometimes we have some stuff left over and we need somebody to handle it.

[Jed Lipinski]

Three days later, Ricko's pager went off. It was the agent. Customs had just made a massive marijuana bust on a small uninhabited island called Horseshoe Cay. He said he wanted Ricko's help bringing some of it to shore.

[Rico DeShaw]

We've already busted it. You're not stealing anything. They're going to take it to the dump and burn it. He said, there's about 10 or 15 bales there that we want for ourselves. I said, we? He goes, yeah.

[Jed Lipinski]

So Ricko took his boat out to Horseshoe Cay.

[Rico DeShaw]

And I remember it very well. It was about 15 bales stacked up there. It's the first time I've ever been on an island where I saw a rattlesnake, because I remember it and it kind of freaked me out, you know, But I was, you know, so I bloated the bales on the boat. I took him back in. He gave me a 2 meter radio to talk on and the frequency and I was off where I was supposed to unload. And I clicked the radio and I said, I'm here. And he goes, okay. He saw the van back up. I pull up, offload the bales. They go inside a federal U.S. customs van. And so I told Dickie about it. And I said, dickie, you're not going to believe this.

[Jed Lipinski]

Everyone Ricko and Dickey knew in the drug business had what's known as a handle, a nickname they used when communicating over the radio. Dickey's was Green Turtle. Ricko's was Sky King. As their relationship with a U.S. customs agent developed, they gave him his own handle.

[Rico DeShaw]

His handle was angel, because he was our Angel.

[Jed Lipinski]

By the late 70s, the heat was turning up in South Florida. Smugglers were getting hit from all sides. Local cops, Marine patrol, Coast Guard, even federal task forces. But Dickey and Ricco had protection at every level, including the feds. While other crews were getting busted, they kept flying under the radar.

[Rico DeShaw]

I got a call from angel one time, and he said, listen, don't put anything on the road. They're busting everything that comes into Florida City. And I'm like, they were busing campers. They were busing dump trucks, they were busing vans. You know, they had roadblocks set up. Meanwhile, the Colombians are screaming at me, you need to get this up here right now. So Dickie and I were about £30,000 in a house, and we were eating breakfast. I know it sounds funny. A school bus went by. I said, dickey, where can we buy a school bus? He looked at me and he goes, what? Where can we get a school bus? He just looked at me and he goes, I don't know. So we wound up going to an auction and buying two yellow school buses. And we took pictures of the one at the high school. We had them painted Monroe County Schools. And what we did is we took a torch and we left the back seats up. You could see above the windows, but we cut the bottom seats out. You could put £11,000 in a school bus, and that's how we transported it. We did that very successfully and never had an issue with it. They just waved the school buses through. We had a Latin guy that worked for us, and we put a wig and a dress on him, and away he went.

[Jed Lipinski]

A wig and a dress?

[Rico DeShaw]

Yes, sir.

[Jed Lipinski]

Was it convincing?

[Rico DeShaw]

Well, they never busted us, you know.

[Jed Lipinski]

As the 1980s approached, Dickie and Ricko began to feel untouchable.

[Jake Brennan]

You know, everybody always says to me, well, tell me about getting chased or tell me about this or that. And I'm like, I don't have those stories, you know, because it was so easy for us to do it.

[Jed Lipinski]

The two working class kids from Islamorada were now raking in millions of dollars a year. But while many of their confederates in Miami flaunted their wealth with Lamborghinis, bodyguards, and oceanfront mansions, Dickey and Rico kept a relatively low profile.

[Jake Brennan]

As you make more money, you want to have a fancier car, you want to have a nicer boat. Or you want to build a nicer house. Although most of us down here really didn't. We weren't too extravagant as far as as houses and cars and stuff. We just, you know, we helped a lot of people down here as far as spreading love and leaving big tips when we'd eat and stuff like that.

[Jed Lipinski]

That said, they were still in their 20s and they weren't shy about enjoying the money.

[Rico DeShaw]

I mean, I would just call him up and he'd say, where are we going? I says, meet me outside. And he goes, what are we doing? This big Learjet comes in and lands. We hop on the Learjet. He says, where are we going? I said, aspen, Colorado. It was a fantasy.

[Jed Lipinski]

What'd you do in Aspen?

[Rico DeShaw]

We went skiing. We didn't have. We had no clue what we were doing. We bought really expensive equipment and rented all these skis and went at the bar and went up on this big thing and we took a couple ski lessons, said, here we are. We had one hell of a good time.

[Jed Lipinski]

But the golden era of pot smuggling was coming to an end. The Coast Guard had expanded its presence dramatically throughout the Caribbean, setting up floating checkpoints and choking off old smuggling routes. Bringing in £30,000 of marijuana on a shrimp boat was no longer practical. The market began tilting toward cocaine. A single kilo fetched 10 times more than a pound of pot and took up a fraction of the space. Ricko remembers the moment he first saw cocaine mixed into one of their marijuana shipments.

[Rico DeShaw]

There was some duffel bags full of stuff that I didn't recognize. I'm like, what's that? I didn't know nothing about cocaine. Zero. Well, that's, you know, it might be.

[Jed Lipinski]

The new product for Dickey and Ricko. As for so many other drug smugglers of the era, the allure of cocaine was obvious.

[Rico DeShaw]

The marijuana was a very laid back, no big deal kind of thing. The cocaine, you really up the odds with the money. For instance, you buy a kilo of cocaine in Colombia for $5,000, you can sell it in the United States for $40,000. So 10 kilos of cocaine just made, what, $350,000?

[Jed Lipinski]

Ricko was earning a legitimate income as a charter pilot. He was also flying loads of pot from the base of the Andean mountains in Colombia to a drop site in the Everglades. Seeing the profits cocaine brought in, Ricko began switching up the cargo. But it wasn't a job for the faint of heart.

[Rico DeShaw]

So we got a hold of the right people, and I'm in this souped up beautiful Airplane here. I go down to Columbia and I'm going. I mean, if you've ever been to Columbia, but it's, you know, you're all by yourself. You're in the middle of nowhere. Once you get down there, you're fuel critical. If you make a mistake, you're probably going to die. If the weather's bad, you're probably going to die. If you come back here and, you know, if you don't do it right, your world of options is very few, and it usually winds up ugly. But I would say it made me a better pilot.

[Jed Lipinski]

According to Dickey, they developed a working relationship with Pablo Escobar, the head of Colombia's Medellin cartel, which at its peak in the 1980s, controlled as much as 80% of the global cocaine trade. The cartel would later be held responsible for thousands of deaths in Colombia. But Dickey, who spoke with Escobar a few times through a translator, had only nice things to say about him.

[Jake Brennan]

He was great. He was always on time. Everything was great with that guy Escobar, yeah, but he, you know, he had a pretty bad reputation down in Colombia, but he was a good man.

[Jed Lipinski]

Ricko didn't feel comfortable flying cocaine into the United States, so he flew it instead to the Abaco Islands, a remote chain in the northern Bahamas. Dickie would meet him there in a 41 foot cigarette boat with a pair of 700 horsepower motors on the back. He'd then transport the load back to his hometown of Islamorada, where his crew offloaded it onto smaller boats and brought it ashore, at which point their job was done.

[Jake Brennan]

I was offloading. I was just, you know, we were bringing it from point A to point B and I was offloading it. It wasn't my merchandise. I never sold any of it. It was just I was handing it off.

[Jed Lipinski]

Dickey and Ricco may have only been the offloaders, the drug trade's equivalent of UPS drivers, but they were still a critical part of the supply chain. The profits from cocaine dwarfed their marijuana proceeds. Dickey bought a new house with an Olympic sized swimming pool. Ricko bought a 66 Corvette, a twin engine Panther Navajo with leather interior, and a pair of jet helicopters.

[Rico DeShaw]

And I'd say to somebody, I'll pick you up out in the parking lot. I'd land a Hughes 500D in the parking lot and pick somebody up and fire up the helicopter and go where I was going to go. It was neat.

[Jed Lipinski]

Dickey, for his part, had begun to feel invincible.

[Jake Brennan]

We had a lot of toys and did what we wanted to do. You know what I tell people that when you get like I had gotten, you get to be where you think you're bulletproof. You know, you're just 10 foot tall and bulletproof and they can't touch me. And that's how you get For Dickey.

[Jed Lipinski]

And Ricko, the good times felt like they'd last forever, but they were about to come to an end. That's next time on Gone South. If you have information, story tips or feedback you'd like to share with the Gone south team, please email [e-mail] that's gonesouthpodcastmail.com and for bonus content, you can follow us on Facebook, TikTok and Instagram @GONE SOUTHPodcast. You can also sign up for our newsletter on substack. Gone south with Jed Lipinski Gone south is an Odyssey original podcast. It's created, written and narrated by me, Jed Lipinski. Our executive producers are Jenna Weiss Berman, Maddy Sprung Kaiser, Tom Lipinski, Lloyd Lockridge, and me. Our story editors are Tom Lipinski, Maddy Sprunkheiser and Joel Lovell. Gone south is edited by Chris Basel and Perry Crowell. It's mixed and mastered by Chris Basil. Production support from Ian Mont and Sean Cherry. Special thanks to J.D. crowley, Leah Rees, Dennis, Maura Curran, Josephina Francis, Kurt Courtney and Hilary Schuff.

[Soraya]

Some people play it safe, but that's never been my style. I'm Soraya and this is Rule breakers, the podcast where we celebrate the rebels, the misfits, and the ones who make their own way. Every week I sit down with athletes, entertainers and industry disruptors who don't just push the boundaries now, they shatter them. We talk about the wildest risks they've taken, the lessons they've learned, and the moments that made them who they are. No filters, no bs, just real talk of people who are refuse to follow the script. And we don't just talk about breaking the rules now we prove it. Think dog shot collars, bug trivia, blindfold tattoos and text roulette. The stakes are high and the chaos is real. So if you've ever been told to stay in your lane, this show is for you. Follow and listen to Rule breakers with Saraya, an Odyssey podcast available now for free on the Odyssey app and wherever you get your podcasts.