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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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."

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.

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.

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.