With George Thorogood’s “Bad to the Bone” blaring from the cockpit tape deck, Richard Pitt maneuvered the Cessna 404 onto the paved runway in the small southern Mexican border town.
He’d done this many times before, navigating mountain passes and perilous jungle runways, all the while on the lookout for police, guerrillas and bandits wanting to steal his cargo. This load, however, was the most he’s ever carried at 600 kilos of cocaine valued at more than $27 million.
It was the heyday of drug smuggling in the 1980s, and Pitt was right in the middle of it.
How did a kid from Thermopolis, Wyoming, and a Vietnam veteran, who had worked his tail off to become a commercial airline pilot end up smuggling for Pablo Escobar?
Well, that’s the part of his story Pitt is still working out for himself as he looks back on his life all these years later.
Some memories are more dramatic than most, Pitt told Cowboy State Daily, in his first-ever media interview. And in a life lived on the edge, that’s saying something.
Even before Pitt put the plane down on the runway in Palenque, Mexico, that day in 1982, he’d already had a bad feeling.
This was accelerated when he tapped the brakes and heard a popping sound that sounded a lot like a brake line. With his heart racing, Pitt fluttered the remaining brake while pulling back on the right rudder, eventually stopping at the edge of the runway as he stared down at the 12-foot drop he’d almost plummeted into.
As his hired ground crew drove up to meet him, he knew something was off. He’d soon learn that his instincts were dead on when he saw two pickups filled with Mexican military there to greet them.
“They got us,” he said. “There was no way out of it.”
Biggest Bust In Mexican History
Loads this size were unheard of at that time.
Pitt knew he was taking a great risk hauling so much cocaine, but his Colombian sources had thousands of kilos sitting off the north coast of Colombia that needed to be moved. They called Pitt, and he’s not a guy who declines an offer.
“I never refused anyone in need of help,” he wrote in his memoir-in-progress, shared with Cowboy State Daily. “I should have that day, or at least thought it through more thoroughly.”
Soldiers dressed in oversized jungle fatigues with rifles slung over their shoulders took Pitt, his two passengers and two ground crew members into custody. Dirty bags were slung over their heads as hoods as they were carted off to a Mexican army garrison, where guards took turns beating and torturing them.
Even today, Pitt has vivid flashbacks to the beatings, including being put on a block of ice where they electro-shocked his genitals.
They wanted to know the source of the cocaine, but Pitt and crew didn’t give up names, instead concocting a story and taking the punches.
Making Headlines Back Home
The Mexican authorities regardless hailed it a victory, declaring it the largest cocaine bust in history as they paraded the badly bruised Americans in front of the press while sensationalizing details, including adding a shootout that never happened and declaring them members of some unnamed mafia of which none were affiliated.
The Associated Press quoted the Mexican army’s statement, describing the “narco-traffickers” firing “high-powered weapons against the Mexican army, who repelled the attack.”
None of that was true, Pitt said. They were unarmed and surrendered peacefully.
Nonetheless, the headlines were also picked up by media outlets back home, where Pitt’s mom, Nora, happened to be sitting on a couch in her daughter’s home in Washington in front of the television.
“Is that Richard?” she asked her daughter, Mary Dell.
Nora had just been to Florida to visit Pitt, his wife and young granddaughter and had been impressed by his fancy yacht and movie studio. She figured one of his movies must have made it big.
Mary Dell squinted at the screen in disbelief.
“Mom, I don’t think that has anything to do with Richard’s movie business,” she said.
This was Nora’s first inkling that her son was more than just a commercial airline pilot and movie producer.
Pitt was told this story when he returned to the states less than three months after escaping the Mexican prison. He and two other men had gotten the guards and other inmates stinking drunk on whiskey, then scaled the wall and fled about 100 miles on foot through a snake-infested jungle.
He’d keep that story to himself as he attempted to steel up the nerve to face his mother. Even today all these years later, Pitt remembers how terrified he’d been to walk into his sister’s house that day.
“It was the scariest thing I’ve ever done in my life,” he told Cowboy State Daily. “Worse than any torture.”
Pitt’s mom proceeded to glare at her son, telling him that he was probably the dumbest person she’d ever met in her life for attempting to take on the Mexican military in a shootout.
Didn’t he realize that would just have made them madder, she told him.
That it hadn’t occurred seemed beyond the point as she continued to chastise him.
Then she told Pitt that maybe he ought to step back and think about what he was doing with his life.
Spy Novel On Steroids
Today on the other side of 70, Pitt has spent a lot of years thinking about his life.
Most of those years were in federal prison in Pennsylvania where he spent 28 years. He’s been out for five years and now lives a quiet life in Denver near his daughter, where he continues trying to repair their badly damaged relationship.
He no longer flies planes but instead has a commercial driver’s license and works intermittently as a truck driver.
He also does a lot of writing.
In prison, he wrote a three-part spy trilogy starring protagonist Yancy Lightfoot that’s based on his own exploits. Now, he’s at work on a memoir, after a prompting from his daughter who had asked him on a prison visit why he had missed out on all those years of her life and his grandchildren.
It’s safe to say that Pitt has no shortage of material.
In fact, his own life reads like a spy novel on steroids, where it’s impossible not to periodically stop him and ask him to repeat himself.
There’s a reason that his close friends call him “the most interesting person they know.”
In fact, while in prison, a former FAA inspector and self-published writer stole Pitt’s story and wrote a book under Pitt’s name, even using Pitt’s photo on the front cover. A fellow inmate told him about it, at which point Pitt’s lawyer sent the plagiarist a cease-and-desist letter to shut it down.
Even Pitt seems caught off guard by his stories from time to time, which he shared over a course of several phone calls.
“To think I’m just a dumb guy from Podunk, Wyoming,” he said.
First Flight Over Greybull
Pitt grew up in Thermopolis, a town he still reveres and even wrote a guidebook about when he was in prison.
Born to alcoholic and drug-addicted parents, Pitt said he spent the first four months of his life being left in a car while his parents were in the bar drinking. When he came down with pneumonia at age 4 months, his birth dad’s brother, Milo, and his wife, Nora, stepped in to adopt him.
In his memoir, Pitt writes about being grateful that his parents gave him up.
“This is where luck stepped into my life and hit a home run,” he said.
His adoptive parents worked and ranched, and he grew up herding cattle and doing other ranch chores like many Wyoming kids. He writes longingly about all the lessons learned from his father out on the range, 40 miles from home.
From a young age, Pitt knew he wanted to be a pilot and didn’t consider doing anything else.
It all started with his first flight over the tiny town of Greybull, which he said he still remembers clearly to this day. It had been a generous gift from Mary Dell for his sixth birthday.
From that moment he was hooked, Pitt said.
It wasn’t the views from 1,000 feet up above that captured Pitt’s imagination, but rather the mechanics of flight itself and what the pilot was doing to keep them suspended in air.
He was so mesmerized by the gauges and nobs that the pilot had to remind Pitt to look down out of the window.
Years later in prison, Pitt would tease Mary Dell that she’d provided him with the gateway drug to smuggling.
“I think she wanted to beat me senseless, Pitt said. “But truthfully, there’s nothing I could have done to change the direction that I was going. I was addicted to adrenaline. It was my drug above all else.”
Pipeline Pilots
Pitt was a poor kid with a penchant for a rich man’s hobby and occupation. He had to work his way up from the bottom.
At 11, he landed a job snagging golf balls at the new driving range next to the airport where he longingly watched planes come and go. One day, he walked over and asked pilot, Mel Chrysler, if he needed any help washing his plane.
“He must have seen my enthusiasm, because he offered me a job doing odd jobs around the airport,” he said.
In lieu of payment, Pitt asked for flying time. Eventually, he started helping other pilots with basic maintenance work, which he enjoyed, taking home airplane manuals and studying how every part fit together.
Here he also came into contact with pipeline pilots whose job it was to fly low over the buried oil pipelines running from Montana to central Wyoming to look for leaks and ruptures.
He asked if he could come along, and with his parents’ approval spent long days twisting and turning through the Bighorn Basin at 50 to 150 feet above the ground.
Brightly Colored Envelope
After high school, Pitt moved to Seattle in August 1967 to work as a flightline mechanic for Boeing. Two years later, he joined the U.S. Air Force, where he flew C-130s and other large cargo planes in Vietnam and also became an instructor.
At 27, he finally realized his dream of becoming a commercial airline pilot for United.
His good friend and mentor David Guinn was a United pilot at the time. The two had met at a skydiving club in Maryland and became good friends. When a job opened training other pilots to fly DC-8s and 727s, he encouraged Pitt to apply.
“Richard was really the person that when he picked up a book to study something, he didn't put it down until he knew everything in it, and so I encouraged him to put in an application,” Guinn told Cowboy State Daily from his home in Texas.
He suggested Pitt send it in a brightly colored manilla envelope so it would stand out among the hundreds of other applicants.
Whether that actually worked is anybody’s guess, but Pitt got the job, Guinn said. Later, Pitt also became a qualified crew member on the Boeing 727 flying passenger routes across the United States.
“He had lots of opportunities to be a good pilot, but he chose to leave the airlines,” Guinn said. “He wanted a more exciting life, I think.”
Lured To The Dark Side
Pitt would agree with that, he said, and for him it became all about chasing the next adrenaline rush. Plus, the routine commercial flights bored him when compared to his worldwide travel in the Air Force.
Initially, it was about the money.
At the time, Pitt was going through a divorce from his first wife, and he needed a down payment for a lake property he had his eye on at Lake Tapps in Washington state.
As a new pilot still on probation, his salary was about $900 a month. At the time, he was also flying for the Air Force Reserves. He ran into a crew chief he’d known from years before who was smuggling on the side.
The two had been together on a flight to Laz Paz, Bolivia, they’d stopped to refuel. Pitt saw him sneak something into one of the cargo bins but looked the other way after the guy asked him not to tell anyone.
Later, the guy showed up at his place with an envelope full of $100 bills.
On a chance encounter, he ran into the guy months later when they’d both landed and talked over coffee. Pitt told him about his impending divorce and need for down payment. One thing led to another, and the guy introduced him to some people.
On his first run, Pitt made almost the entire down payment for the house.
“If I hadn’t stopped for coffee, who knows where I’d be today,” he said.
Meeting Escobar
Mostly Pitt worked through his cartel-affiliated contacts and middleman until one day he was called in by Pablo Escobar, the notorious “King of Cocaine” and founder of the Medellin Cartel in Colombia, who monopolized the cocaine trade in the United States in the 1980s and 1990s.
Pitt had no idea why he’d be summoned but waited in line as men walked in and out of Escobar’s office assembly-line style.
When it was his turn, he sat down in the still-warm, plush green leather chair where Escobar stared at him over his desk. Men lined the back wall while others watched him from in front of the window.
Pitt shook Escobar’s hand.
He’d been called in, Escobar explained, because Pitt had embarrassed him in front of one of his employees. Escobar was referring to Pitt’s storming into his middleman Caesar’s house to demand the $40,000 he owed him from the last load of cocaine.
Escobar wanted to know why Pitt didn’t reach out to him directly.
“I’m sorry, Don Pablo,” Pitt had said, “but I didn’t have your phone number to call you down here. Or God knows, I certainly would have.”
The room broke out in laughter — except Escobar, whose right cheek barely twitched in an almost-smile. From then on, Pitt was to contact Escobar directly if he had any issues and was promised $4,000 per kilo hauled.
It was then he realized that Caesar had been skimming off the top all along and cheating him. Pitt never saw Caesar again.
Driven By Adrenaline
This is just one story of many that Pitt has about his years smuggling cocaine for the Medellin Cartel between 1977 to 1986.
As for feeling guilty about bringing copious quantities of drugs into the U.S., Pitt said that would take a few years to catch up with him. It was a different era then when smuggling and drugs were prolific, and you could spot another smuggler in Miami just by his cocky gait.
Guinn agreed that a lot of pilots gave in to the dark side. One plane he sold to a guy, he later found out, was used for smuggling. He, himself, had been offered money to smuggle drugs once.
“I said ‘no’ so fast that I almost fell down,” he said.
Pitt, however, was driven by the adrenaline.
“I was an adrenaline junkie,” he said. “It wasn’t about the money.”
In his memoir, Pitt writes about his experience “flying at midnight at 300 mph over shark-infested waters at 10 feet above the ocean, flying through thunderstorms, flying across communist countries (Cuba) and landing on runways that you wouldn’t want to walk down in the daytime, let alone land one at night because there so rough.”
He survived three plane crashes and several encounters with guerilla groups and other smugglers, including being robbed in the Caribbean and returning to steal it all back, much to the disbelief of the Colombians who prized Pitt as one of their finest pilots.
The copious amounts of money were equally insane, Pitt said.
It afforded him a yacht, a movie studio through which to launder his money, and at one point he owned 21 airplanes. It also got to be too much, he said, and it was exhausting to continually try to find ways to launder the money and break huge bills.
He got to the point where he just started giving money away to anyone who needed it, much to his wife’s chagrin.
Along with smuggling, Pitt was also a prolific skydiver who set a Guinness World Record for jumping from Angel Falls in Venezuela in 1983. For Pitt, that was another outlet for his adrenaline.
He had no interest in doing the drugs he was smuggling, he said, but rather for him it was all about the thrill and continual near-death experiences.
“I was always after the next adrenaline rush,” he said.
Extradition To Mexico
The law finally caught up with Pitt for the first time in Denver in 1985.
He was fresh from the airport and riding home in taxicab, excitedly reading a screenplay when an FBI agent knocked on his window and asked him to get out at gunpoint.
Ironically, Pitt had pretty much decided at that point that he was done with smuggling and instead wanted to focus on making legitimate films and designing stunts.
He had just crafted a stunt involving a cartwheel crash of a DC-3 that was slated to be used in the movie“Good Morning, Vietnam” with world-renowned stuntman and director Glenn Wilder.
He’d met Wilder years earlier when he hired him to direct “Masterblaster,” a 1987 action thriller about a paintball tournament turned survival exercise after a killer starts eliminating the competitors, which was produced by Pitt’s film studio, First American Entertainment.
Initially, Pitt’s three film companies in Florida and the United Kingdom were fun propositions by which to launder his money. They primarily made commercials and some motion pictures.
But he was getting serious about turning his studio into a legitimate business. Wilder died in 2017, but his widow, Amy, also a prolific stuntwoman with credits such as “True Lies” and other action-packed movies, has known Pitt for more than 40 years.
Pitt hired her as his secretary in 1984 after a chance meeting in the parking lot. This is where she met Wilder, and her life took a curve. Up until that point, she had planned to go to law school but instead became a stuntwoman.
At first, she had no idea Pitt was a drug smuggler or where his money was coming from.
“It should have been a big red flag the time he handed me a briefcase to keep under my desk with a million dollars in it,” she said with a laugh. “I was really naïve back then.”
She didn’t work for Pitt for long before he was picked up in Denver and extradited to Mexico when all of his business dealings fell apart.
She and her husband stayed in close contact with Pitt over the years, and when he was incarcerated for the second time in the U.S. after his return from Mexico, she typed up the longhand stories he sent on legal pads.
It was then she got a better understanding of what Pitt had been doing, but like his other close friends, she didn’t hold it against him. Despite his crimes, it’s his character that matters, she said.
“He’s a very fascinating and smart guy and a very talented pilot,” she said. “He wanted a more exciting life full of adventure.”
He’s also one of the kindest, most generous men she’s ever met, she said, and was a really good father when he was around.
'Hellish Hole'
Pitt was also one of the first Americans to be extradited to Mexico following the passage of a treaty in 1978that took effect in January 1980.
After being arrested and carted into the Denver jail, FBI agents visited Pitt to explain they had an extradition order for him stemming from his earlier escape from the Mexican prison. This caught Pitt off guard, he said. Had he known about it, he would have paid off officials in Mexico.
Pitt would be one of the first Americans to be extradited.
He was later told by someone affiliated with the U.S. Justice Department that the U.S. was eager to get their hands on Caro Quintero for killing DEA agent Enrique “Kiki” Camarena in Mexico, and Pitt was a pawn worthy in the political game of chess.
Two DEA agents also visited him at the Denver jail where he sat for 18 months awaiting extradition to see if he cared to share any information about his drug smuggling “friends,” to which Pitt declined.
Instead, he was shipped off to Mexico and thrown into what he called a “hellish hole that made ‘Midnight Express’ look like a luxury retreat.” He slept on a concrete slab in a rat-infested cell next to a Mexican-born hitman who had just been deported from Chicago.
Oddly, Pitt credits those initial conversations with the hitman for keeping him sane. That and his military training that taught him the essentials of staying alive.
He underwent months of psychological and physical torment and lost more than 50 pounds.
Eventually, his friends would arrive with money and items to improve his stay, including a pink toilet for his cell. If you have money, you can pretty much get anything you want, he said.
His mentor David Guinn and his wife visited Pitt every few weeks during his five-year incarceration on visits to the children’s home they helped run in southern Mexico. Pitt described his shame in having his mentor see him behind bars for what he'd done.
Guinn was impressed by Pitt’s fortitude and his ability to thrive in an otherwise terrible environment by teaching weightlifting and bodybuilding to kids and making gym equipment. He, like Pitt’s other close friends, stood by him despite his crimes.
“We can’t really judge each other,” he said. “But I love the guy. His perseverance and ability to survive is really quite astounding.”
Again, Back To Prison
After five years in Mexico, Pitt, then 46, returned to the United States in the early 1990s and began working with U.S. government intelligence agencies as part of a plea deal after he was caught transporting less than a pound of cocaine in his van in Miami, according to media reports from that time.
In exchange for a lighter sentence, Pitt helped the agencies with some major busts, including undercover work in Texas that netted a $1.3 million in cash.
Then, something went south in his work with the U.S. Customs Service, when he was accused of operating out of bounds.
Pitt is vague about what went awry with these dealings and how he and his partner were arrested and spent 28 years in prison on charges of transporting cocaine for sale and money laundering.
Pitt said that story has yet to be written and will be one day soon, but court records indicate the agents did not give him permission to break the law.
At question specifically is 486 kilograms of cocaine he and his associates had in their vehicle when they were pulled over by a state police officer in California.
The two agents he was working with said that Pitt had not informed them of his plans to transfer the cocaine from New York to Los Angeles, nor did they authorize him to engage in criminal conduct during the course of the operations and wasn’t authorized to distribute the drugs, according to court documents.
For his part, Pitt said the shipments were a necessary predicate to pulling off the reverse sting operation, but the government claimed otherwise.
Pitt said that there’s much more to this story still to be told as well as evidence in his favor that “disappeared” following his arrest.
“Everything that was involved is another book that is still being written,” Pitt said.
Instead, he pleaded guilty to the charges and served his time. He was released from prison in 2020 under compassionate release laws implemented during the coronavirus pandemic.
Flashes Of Home
Once in prison, Pitt devoted himself to studying the law and connecting with his longtime friends.
Joe Doak, who died last April, was surprised when Pitt called him 25 years ago from prison, according to Joe’s widow Linda.
Initially, Linda said they feared Pitt was looking to borrow money, she laughed, which couldn’t have been further from the truth. Pitt just wanted to talk about old times and people they’d grown up with.
After that initial phone call, Pitt and Joe talked frequently with Joe sending Pitt a subscription to the local newspaper that he shared with the other inmates who couldn’t believe such a town existed where someone’s lost dog being returned made front-page news.
“Most were not even aware of these small communities,” she said.
Along with their phone calls, Pitt would send the Doaks chapters of his books and memoir-in-progress, which they both found astounding.
All they had known about Pitt after he left Wyoming was that he’d been in the Air Force and became a pilot for United Airlines. The smuggling and subsequent prison sentence was a shock to them.
But no judgement, she said. They consider him a lifelong friend.
When Joe died, Pitt printed a eulogy to him in the paper and was there for his funeral. Pitt also dedicated his latest book, “Going Critical,” to Joe. The couple has all his books, Linda said, and has enjoyed reading about Pitt’s life.
“He lived his life to the fullest, and was able to write it all down,” she said.
Former Hot Springs Sheriff and County Commissioner John Lumley also remembers Pitt from high school and even ran his plane N-number when he came home for a high school reunion.
“I heard he was getting into some stuff, and they were looking at him,” he said.
It’s a small town and he remembered Pitt as a “thrill seeker” and good athlete. He also said Pitt is a guy who doesn’t lie.
Lumley talked to him when he got out of prison.
“I told him he served his time, but he’s got one more person to talk to and one more goal to achieve and that’s when he passes on, he’s got to answer to another for what he’s done,” Lumley said.
The Next Chapter
Pitt knows this, and said he’ll spend the rest of his life atoning for his past crimes as he tries to forge a relationship with his reluctant daughter.
“I wrecked her life, and there’s no doubt about it,” he said.
She was only 5 when he was extradited to Mexico, and he wasn’t around for most of her life.
He relistens to his favorite song, “Reluctant Daughter” by Martina McBride, with one line in particular that resonates with him: “Jesus, tell my father I wanna be his child again. Tell him what my name is in case he’s forgotten.”
He gave in to his drug — adrenaline — in lieu of taking care of his family, he said with the steely-eyed reserve of a man looking back at a life that severely swerved off course.
There’s also the wreckage of the drugs he brought back into the country that paved the way to the crack epidemic to follow. He’s lost close friends to drugs, including Paul Newman’s son Scott, who died of an overdose in 1978.
“I have to live with that,” he said.
Does he have regrets? Heck yeah, Pitt said, but now he plans to spend the rest of his life attempting to prioritize what he says truly matters: family, faith and love that take precedence over his fleeting pleasures.
There’s a reason he’s still here, still breathing and able to tell his story. And he doesn’t plan to squander it.
Jen Kocher can be reached at jen@cowboystatedaily.com.
