This Florida Drug Smuggler Escaped 7 Life Sentences—Twice
For a long time, Richard “Dickie” Lynn didn’t think he’d ever see the mesmerizing blue waters of the Florida Keys again.
The former drug smuggler and onetime escapee from federal prison had received seven life sentences after he was convicted as part of a massive 1989 drug trafficking sting. He was released last June after serving 31 years.
I caught up with Lynn, 66, a few months after his release. Today, he sports a mop of light brown hair and a graying goatee. He’s back in his element, wearing the typical Keys uniform: performance fishing shirt, shorts, and flip-flops.
I wanted to talk to him not only because his story is a wild true crime tale involving Cuban dissidents, former U.S. Attorney General Jeff Sessions, and corrupt Customs agents. I wanted to talk to him because the prosecution, incarceration, and improbable release of Dickie Lynn shows how the drug war warped the criminal justice system, and how the country has slowly tried to fix it.
From the harsh sentences of the 1980s to the criminal justice reform movement of the 2010s, Lynn experienced it all. His life story is also the tale of four decades of the U.S. criminal justice system—its failures and flaws, and its recent turn toward redemption.
Florida Man Has Fast Boat, Drug Smuggling Business
Lynn grew up in the Florida Keys, the chain of small islands that runs past the tip of mainland Florida for 125 miles, terminating in Key West. The area has been a smuggler’s paradise for as long as there’s been contraband to smuggle. The Keys backcountry is dotted with hundreds of small, uninhabited islands and twisting mangrove channels. It’s close enough to get to Cuba or the Bahamas by boat, South America by plane, and Miami by road, making it an ideal stopover for inbound drugs.
Longtime Keys residents will tell you about taking Jon boats out as teenagers to look for “square grouper”—a joke term for the stray bales of dope that sometimes drifted into the mangroves after drug runners threw them overboard while fleeing the Coast Guard and other authorities. Locals like Lynn soon discovered there was an obscene amount of money to be made using their knowledge of the local waters to run pot.
Back then, the tools of the trade were a fast boat, steady nerves, a friend with a radio scanner to keep an eye on military and law enforcement chatter, and a roll of quarters for the pay phones.
“You know when Jimmy Buffett says, ‘Rule my world from a pay phone’?” Lynn asks, referring to a line from the song “One Particular Harbor.” “That’s what it was.”
Federal prosecutors estimated that one of the largest marijuana trafficking rings in South Florida grossed $300 million between 1977 and 1981. One pilot from the era estimated he made $750,000 to $1 million over two years just smuggling pot. The amount of money that was flowing into the local economy meant no one was complaining too much, either.
“If they weren’t smuggling with us or working on our boats, we were building houses or lending them money to start a restaurant,” Lynn says. “Mothers used to sit around and listen to scanners in case somebody was throwing something off the boat or whatever.”
Key West was so corrupt that a 1975 state and federal crackdown on the tight-knit network of local drug traffickers netted, among others, the city attorney and the fire chief, Joseph “Bum” Farto. Farto disappeared in 1976 while awaiting sentencing. He told his wife he was driving up to Miami for the day and was never seen again. The question “Where is Bum Farto?” has haunted Key West ever since.
As marijuana gave way to cocaine in the late ’70s, the potential risks and rewards of smuggling exponentially increased. Lynn and a small crew upgraded from airdrops and runs of pot from Jamaica and the Bahamas to running flights of cocaine from South America to rural Alabama, where they operated out of a remote hunting camp.
According to Apprehended: The Trials of Dickie Lynn—a 2013 book by Domingo Soto, one of the defense attorneys in Lynn’s case—the pilots would take off from South Florida, fly to Colombia, and load up the plane with duffel bags full of cocaine. The pilots would then fly to Belize and land on a road cutting through a sugar cane field, where they would hand the locals $50,000 in cash in exchange for a refuel and a bag of fried chicken. After taking off again, they’d head back across the Caribbean toward the Gulf Coast.
At about 125 miles south of the coast, the pilots would drop their altitude and cut their speed, hoping to appear on radars like one of the helicopters that shuttles back and forth from offshore oil rigs. Lynn was responsible for the ground crew in Alabama, which would meet the plane at one of the lightly used airstrips nearby, offload the coke, and get the plane back in the air as quickly as possible.
A series of mishaps set the smuggling ring’s downfall in motion. In 1986, the pilots had to abandon an entire load of drugs at a small airport in Mississippi because their intended airstrip was covered in fog. The unexpected appearance of 700 kilograms of cocaine did not go unnoticed by local and federal law enforcement. The Jackson Clarion-Ledger declared it “the largest load of cocaine ever seized in Mississippi,” though the use of “seized” was a rather generous characterization of the role of law enforcement.
A year later, one of their planes exploded while trying to land on a foggy night, killing the two pilots. Law enforcement discovered a crash site strewn with hundreds of bundles of cocaine.
Finally, in 1988, police responded to a report of unusual lights at a small airstrip in Perry County, Alabama. They arrived just as the smuggling ring’s Cessna 404 Titan finished refueling. The pilot flipped on all the lights and sped down the runway at the advancing police cruisers, playing a game of chicken. The cruisers swerved, and the plane took off into the night, while the ground crew disappeared into the surrounding forest.
The escape was short-lived. Authorities caught up with the pilots in Muscle Shoals, Alabama. Investigators had been -piecing together information on the planes and their owners for several years. Both pilots flipped in exchange for immunity, agreeing to wear wires to further implicate others in the smuggling ring.
Jeff Sessions Offers Life in Prison
In 1989, the Justice Department indicted Lynn and 21 others in a sprawling drug trafficking investigation. The indictments included four U.S. Customs agents who were on the take.
One of those agents was Charlie Jordan, the marine enforcement station chief in Key Largo and self-declared “ruler of the Florida Keys.” Jordan had gone on the lam two years earlier after he was indicted on other charges, leading to an appearance on America’s Most Wanted and a nationwide manhunt that ended with his surrender in Wyoming.
Two of the organizers of the smuggling operation were Cuban dissidents Andy and Fernando Pruna. Fernando was a counterrevolutionary who had spent 17 years in one of Fidel Castro’s prisons. Andy was among the small team of frogmen—underwater de
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