Summary of "Gone South: Once Smugglers | Part 2"

Introduction

In Season 4, Episode 27 of Gone South, titled "Once Smugglers | Part 2," host Jed Lipinski continues the riveting saga of Dickey Lynn and Rico Deshaw—two childhood friends from the Florida Keys who transitioned from modest beginnings to become prominent figures in the Southern drug smuggling scene. This episode delves into their rise, the complexities of their operations, their entanglement with law enforcement, and the eventual downfall of their illicit empire.

Early Beginnings and Rise in Smuggling

Dickey Lynn and Rico Deshaw grew up as working-class friends in Islamorada, the Florida Keys, where their shared love for fishing and boating laid the foundation for their future endeavors. However, the burgeoning marijuana trafficking era in the late 1970s provided them with lucrative opportunities that they couldn't ignore.

“We came of age at the dawn of the marijuana trafficking era. We became pot smugglers instead.”
— Rico Deshaw ([02:01])

Leveraging connections with local law enforcement, the Coast Guard, and a corrupt U.S. customs agent, Dickey and Rico quickly built a profitable smuggling operation. By the late '70s, their enterprise was pulling in millions annually, expanding further with the rise of cocaine.

The First Major Bust

In 1980, Dickey faced his first significant legal challenge when a potential client shifted demands from marijuana to Quaaludes and later to cocaine.

"So we drive to Miami and set up this deal to buy this kilo cocaine and we get busted."
— Rico Deshaw ([03:38])

Caught in a DEA sting, Dickey was falsely portrayed as a kingpin of the Florida Keys' drug trade. Despite never having sold drugs before, the indictments painted him in a false light due to misleading information from an informant.

“While his co-defendants got 18 months, Dickey got 30.”
— Jed Lipinski ([04:20])

Life at Eglin Air Force Base

Dickey was sentenced to a federal prison camp at Eglin Air Force Base, also known as Camp Fed—a low-security facility with amenities like racquetball courts and sports fields. More importantly, it was a networking hub for inmates involved in the South Florida drug trade.

“It's like my sister said, it was a finishing school. I met Colombians there, I met pilots there, I met boat captains there.”
— Rico Deshaw ([05:02])

During his time at Eglin, Dickey formed crucial connections, notably with George Valdez, a key figure in the Medellin cartel. These relationships would later prove instrumental in expanding their operations post-release.

Innovative Smuggling Techniques

After serving 18 months, Dickey returned to the smuggling scene, determined to escalate their operations. One of his notable innovations was flying over Cuba to save time and fuel during drug transport from Columbia to the Bahamas.

"I would fly across Cuba in the middle of the night at 100ft... they couldn't see me."
— Dickey Lynn ([06:28])

This audacious move dramatically reduced transit time but increased the risks, especially as law enforcement strategies evolved.

Expanding Operations to Alabama

Seeking areas with minimal law enforcement presence, Dickey and Rico invested in a 300-acre hunting camp in western Alabama. This strategic move allowed them to operate under the radar, away from the constant scrutiny of South Florida authorities.

"When we bought the hunting camp, flying into Alabama seemed like a smart move because the scanners in Alabama were quiet compared to Florida."
— Rico Deshaw ([07:43])

In Demopolis, they established a more permanent base, utilizing an existing airstrip to streamline their smuggling routes.

Partnership with Fred Hartley and Tragedy Strikes

Dickey's partnership expanded when he teamed up with Fred Hartley, a talented pilot and former Marine. Together, they elevated their smuggling operations, making substantial profits.

"We had a 404 Cessna we were going to use, and we were going to actually be flying to Guatemala."
— Rico Deshaw ([33:26])

However, tragedy struck when Fred and his brother died in a plane crash while on a smuggling run. This incident deeply affected Dickey, reinforcing his belief in his invincibility and his addiction to the high-stakes smuggling life.

"It was nothing like the rush of hauling $7 million worth of cocaine through the Caribbean on a speedboat."
— Jed Lipinski ([15:35])

The Second Arrest and Legal Battles

Less than six months after Fred's death, Dickey orchestrated another smuggling operation that led to his arrest. Despite believing they had successfully evaded law enforcement, the DEA had infiltrated their operations using informants.

"They labeled me with false accusations of being a violent drug lord."
— Dickey Lynn ([32:10])

During the trial, Dickey was faced with a barrage of misleading testimonies and corrupt practices orchestrated by prosecutors. While his co-defendants were offered plea deals, Dickey refused to testify against Rico, maintaining his innocence.

“They put People on a stand... They put them on the stand anyway.”
— Dickey Lynn ([27:19])

Conviction and Sentencing

Despite the overwhelming testimony against him, Dickey was acquitted of the most severe charges but convicted on seven counts of conspiracy to import and distribute marijuana and cocaine. During sentencing, the judge employed "acquitted conduct" to enhance his sentence, resulting in seven life sentences without parole.

"They had me as an organizer and a leader of controlling this group of smugglers that I had no clue who they were."
— Dickey Lynn ([25:08])

In a poignant courtroom moment, Dickey and Rico reunited, with Dickey expressing his unwavering loyalty.

“Why didn't you testify against me? I never would, never will.”
— Dickey Lynn ([29:35])

Dickey's Imprisonment and Bold Escape

Serving his time at the federal penitentiary in Talladega, Alabama, Dickey endured initial struggles, including solitary confinement. However, his smuggling expertise facilitated a daring escape by hiding in a produce-filled truck's trap door, evading the marshals and joining the ranks of the nation's most wanted.

"They note that Dickey had ties to the Medellin drug cartel. It also noted that he was armed and dangerous and was a suspect in a contract killing of a drug associate."
— Jed Lipinski ([31:48])

Final Capture and Legacy

Ultimately, Dickey was recaptured after a failed smuggling attempt in Mississippi, where a tip led to a coordinated law enforcement ambush. His final years in prison were marked by stringent security measures, including time in the supermax ADX facility in Florence, Colorado.

In contrast, Rico continued his life as an airline captain until facing his own legal battles under the RICO statute in 1991. Accepting a plea deal, Rico avoided the severe penalties that befell Dickey.

Years later, through persistent advocacy and legal efforts led by law professor Katie Tinto, Dickey was granted compassionate release in 2020 due to his deteriorating health. Reunited with Rico in their hometown of Islamorada, their enduring friendship persisted despite the tumultuous past.

"I used to pray every night, you know, with my wife, for Dickie."
— Dickey Lynn ([36:43])

Key Insights and Reflections

Jed Lipinski uses the story of Dickey and Rico to explore broader themes surrounding crime, loyalty, and the human condition within the Southern backdrop. The episode underscores how deep-rooted friendships and personal choices can lead individuals down paths of both camaraderie and destruction.

Notable Quotes

• “We came of age at the dawn of the marijuana trafficking era. We became pot smugglers instead.”
  — Rico Deshaw ([02:01])

• “So we drive to Miami and set up this deal to buy this kilo cocaine and we get busted.”
  — Rico Deshaw ([03:38])

• “I would fly across Cuba in the middle of the night at 100ft... they couldn't see me.”
  — Dickey Lynn ([06:28])

• “They put People on a stand... They put them on the stand anyway.”
  — Dickey Lynn ([27:19])

• “Why didn't you testify against me? I never would, never will.”
  — Dickey Lynn ([29:35])

• “They note that Dickey had ties to the Medellin drug cartel. It also noted that he was armed and dangerous and was a suspect in a contract killing of a drug associate.”
  — Jed Lipinski ([31:48])

Conclusion

"Gone South: Once Smugglers | Part 2" offers a deep dive into the lives of Dickey Lynn and Rico Deshaw, showcasing the allure and peril of the Southern drug trade. Through meticulous research and compelling storytelling, Jed Lipinski sheds light on the intricate web of loyalty, betrayal, and the relentless pursuit of power that defined their journey. This episode not only narrates a true crime story but also invites listeners to ponder the complexities of human nature and the consequences of one's choices.

For those interested in exploring more gripping stories where true crime meets Southern charm, Gone South continues to deliver insightful and engaging narratives each week.