It is seven o’clock on a humid Los Angeles evening, and business is winding down at a suburban car showroom. I walk past a team of guys polishing Japanese hybrids with bright white rags, past the twenty-five-cent gumball machines and into the air-conditioned office. An attorney has arranged this meeting with one of America’s most mysterious men — who has reportedly had surgery to change his identity — at his place of work.

His name is Alfred Dellentash. When I first punched his name into Google, six months ago, the results were simply baffling. First, there is an archived People magazine article from 1978, titled: ‘TOURING ROCK STARS GO TO AL DELLENTASH WHEN THEY REALLY WANT TO GET HIGH.’ The headline is a clever joke, you see, because the story is about his multi-million-dollar private jet-leasing business, which he built in his twenties: “Among the acts that have chartered Dellentash’s three Convairs, two helicopters and a Boeing 707 are the Rolling Stones, KISS and the Grateful Dead.”

The next hit told me Dellentash was moonlighting as a wingman for two of history’s most deadly criminal organizations, flying Pablo Escobar’s drugs from Colombia to the Gambino crime family in New York. His mile-high empire was a front for the most rock ’n’ roll drug smuggling ring in history. Ironically, Dellentash was secretly getting the whole of America high — hiding in plain sight as a chartered plane provider, and later, a music manager for 1980s acts including Meat Loaf and the Bay City Rollers.

I requested to speak to Dellentash through Jack Dampf, the Baton Rouge attorney who represented him during his 1984 trial in which Dellentash was charged with criminal conspiracy to distribute drugs. As soon as I mentioned the name “Dellentash,” Dampf broke into laughter and told me: “Boy, this is one hell of a story.”

Online speculators have tried to link Dellentash’s name to the famous D.B. Cooper hijacking in 1971 (he was too young and short to have been Cooper), the C.I.A.’s covert operations in South America, and even the 9/11 terror attacks in New York — tinfoil-hat theorists discovered that Dellentash’s father was once a contractor on the World Trade Center. But the truth is not out there.

Here in the car showroom, he is known to colleagues as “Dell.” While I wait, one of them, Susan, tells me her favorite Dell story: She was dealing with an angry customer who was rejected for poor credit. In a rage the thug rose to strike her, but Dellentash came from nowhere and subdued him with an expert arm twist.

And suddenly he is ready to see me.

Today, Alfred Dellentash, sixty-six, is mustachioed and bespectacled, wearing a colorful Hawaiian shirt. If there has been any surgery, I cannot see it. The expensive Italian shoes are the only glimpse of his past, when he infuriated the fusty airline industry by staffing his jet planes with Playboy models. According to feverish reports online, back then he was the equivalent of Richard Branson and Tony “Scarface” Montana.

In an office full of salesman trophies, I politely request his first extended interview since being released from his twenty-five-year jail sentence, of which he served just a fifth. I offer the chance to tell how it really happened, for the first time. But Dellentash explains that his head is compartmentalized — he keeps his past locked in a shadowy corner of his mind. This showroom, he says with a wave of his hand, was the choice he made long ago: to leave his past behind and stop running, to enter civilian life and try to win back the only woman who could keep up with him at full flight. He turns down my request.

Weeks later I am surprised when my telephone rings, and a thick New York accent asks:

“Where do you want to start?”

* * *

Dellentash grew up in the suburbs of New York and sang in a church choir. (Photos courtesy of Alfred Dellentash Jr.)
Dellentash grew up in the suburbs of New York and sang in a church choir. (Photos courtesy of Alfred Dellentash Jr.)

Alfred Dellentash Jr. was born on August 19, 1948, in New Rochelle, New York. His father was an Italian-American building contractor with high-rise goals, and his pianist mother was the head of the local Republican Party. Alfred sang in the church choir but regularly stole the “Body of Christ” wine. He spent his evenings painting model B52 and B17 bombers at home and wanted to be a rock star or a jet pilot, depending on what day you asked.

Dellentash became a frequent truant and a straight-D student by his own admission, preferring hustling in local pool halls, “moving swag” and loan-sharking. He played in local bars with his band instead of studying. At age sixteen, Dellentash obtained his pilot’s license. “I spent every dollar I had buying flying time,” he says. “I thought about becoming an airline pilot, but I figured I only wanted to fly where I wanted to go.” He flunked high school but excelled at aviation school. While his peers raced fast cars, he soared high above them in planes, flying loop-de-loops.

One afternoon while in Florida he borrowed a twin-engine plane to take a girl on a date, landing the aircraft on a strip of sand just in time for the sunset. “It was completely illegal,” he says, “but she was very impressed.” This was “Mad Men”-era America, where the pursuit of material possessions and individual happiness reigned free.

“My father arranged for me to work for a construction firm, where I joined the union and sat on a crane doing nothing. I just felt trapped in his world,” says Dellentash. “My life was all mapped out for me.” In 1971, Dellentash married his high school girlfriend, and they had two children. Any dreams of becoming a pilot or rock star faded like jet plane contrails in the sky as he settled down in a Montvale, New Jersey, house he couldn’t afford. “It tore me apart,” he says. “I had babies at home to look after and that became the priority.”

But domestic life could not ground him for long, and he yearned to escape the daily grind and lift off once again. In 1973, Dellentash spotted an irresistibly priced aircraft for sale in a copy of “Airplane Trader.” “I just wanted to feel that freedom when my plane left the runway, when I could go anywhere I wanted,” he recalls. Dellentash flew to Oklahoma to complete the sale, but learned that the vendor, known as “Flamin’ Eddie,” had been found dead in his bathtub. The plane was a wreck, and in desperation, Dellentash tried to cancel his check. His bank suggested that he take a loan against the title of the plane instead. Remarkably, he left the bank with a check for $300,000 — for a plane worth next to nothing. “I realized I was on to something,” he says.

A young Alfred Dellentash Jr. with his father.
A young Alfred Dellentash Jr. with his father.

Dellentash quit his construction job and set up an airplane sales and charter company at Hanger 17 in Teterboro, New Jersey. Though he used the bank’s cash to finance his spending, he was often too broke to afford gas. Dellentash recalls buying a consignment of light aircraft in Sweden that turned out to be overhead camera planes used for geometric surveys. They had trap doors on the bottom, and when asked if he wanted them sealed, Dellentash said, “No. I’ve got an idea.”

“I’ll buy as many of these damned trap-door planes as you can sell me,” said Lenny, one of Dellentash’s customers from Oklahoma. Under his cowboy hat, Lenny was a shaggy-haired triple-A athlete who chose booze and girls over the big leagues. Dellentash knew Lenny and his boys flew bales of pot from Mexico, and dropped their load into fields across the Sooner state without even landing. Everyone was doing it, Lenny said. Together, they figured the trap doors would be perfect.

A 1970s New York Times editorial titled FLYING DRUG-RUNNERS REAP BIG PROFITS described these early, aerial smugglers: “They fly low and slow and by the light of the moon, and make $50,000 a night.” The piece quotes a Customs agent, who said: “Anybody who knows how to fly can get into the business and make a lot of money in a hurry if he can get away with it.” Dellentash was intrigued.

“You know anyone who can pick up 1,500 pounds of marijuana?” Lenny asked, one afternoon.

“Where is it?” said Dellentash.


“Why not?” When opportunity knocked, he always answered.

Dellentash leased a plane for the occasion and flew a rare push-pull Cessna Skymaster 337 over Central America, with propellers on the front and back of the aircraft. It was the first time Dellentash had flown one, and it was certainly the first time the Belizeans at the airport had seen a push-pull aircraft, because one of their men walked around the back and strolled into the rear propeller, still running at full speed. “It was a mess,” says Dellentash. The propeller almost decapitated the man, who fell with blood bubbling out of his nose and mouth. Someone finished him off with a revolver, Dellentash recalls. “It was a horrifying glimpse into my future.”

Dellentash decided against the drug game, instead using his title loan scam to buy more planes with the bank’s money and lease them to rich businessmen. He found a bank in Oklahoma that wasn’t part of the FDIC and wrangled a $200,000 line of credit. This was the era of the “check float” that enabled many con artists: After a check was deposited, three days were required until the funds were debited from the payer’s account. As a result, a check writer could expect to receive approximately nine days of free money. And with that, his Cessnas became Falcons, and those Falcons became Learjets. As America entered the “Me decade” of the 1970s, one man was climbing faster than the rest, and he wasn’t looking down.

But running an airline like Dellentash’s required a 121 Air Carrier Certification from the Federal Airline Authority (FAA), which involved boring application letters and safety checks. Dellentash bypassed the requirements by calling his business a leasing company instead of an airline. He cleverly ran a separate crewing company to dodge the rules. The FAA was not impressed.

In the late 1970s, agent Charles P. Braunstein was assigned to both the New York and New Jersey FAA offices and tasked with investigating fraudulent Air Taxi certifications. “Most operators I met during that time were cordial and interesting to know,” Charles Braunstein told me in an email. “But in each case I was disappointed to find out they were involved with drugs.”

In 1977 the agent was assigned to Dellentash’s “Triple-D” Corporation. He would spend years chasing Dellentash, whose company was — in Braunstein’s words — the epitome of the fly-by-night airlines that were a danger to American passengers.

When he secured the contract to fly Abdullah bin Abdulaziz Al Saud, the third in line to the Saudi throne (and now the king), Dellentash’s aircraft received automatic diplomatic immunity, taking him above the clutches of the FAA. And the more luxurious the planes he hustled, the richer and more fabulous his clients became. Mick Jagger inquired about a private jet, and Dellentash piloted a helicopter from New Jersey to Woodstock to pick him up.

Within months, he was the personal pilot for the Stones, Emerson, Lake & Palmer, The Grateful Dead and John Denver. He financed the purchase of a Falcon jet by forging signatures on a 300-page loan agreement after a bank turned him down. The planes were a key to the lifestyle he was chasing: More planes meant more money, and more groupies and as much fun as he could handle — as long as he was home for Sunday dinner with his family, like any good Italian-American husband.

The cash and rock connections inspired Dellentash to dabble in his own music pursuits: He dreamed of becoming a music mogul like his famous passengers. He started talent-spotting in New Jersey bars, where he discovered a band called Whiplash. “I said, ‘Let me manage you, I’ll make you huge!’” Dellentash marched them to Manny’s Music and let them spend $30,000 on guitars. “I was at my happiest then,” he says. “I was living a life other kids from New Rochelle could only dream about.” His wife was also struggling to keep up with him. “I tried to involve her in my world,” he says. “She didn’t want to go to rock concerts — she wanted to be at home. I felt like I was torn between two worlds.”

Dellentash’s planes had fully stocked bars, king-sized beds, gold fixtures, thick carpeting, plants, phones, telex printers and electric typewriters, all unheard of in-flight luxuries at the time. “I got great contacts with film people, TV, rock promoters and managers,” he boasted during the People magazine interview. “I got a lot of money and a good business sense.” The article also earned him some unusual attention.

* * *

Miami International Airport, Florida — A piano-black Lincoln town car idled on the street. Leaning against it was a barrel-chested Italian-American clutching a leather purse, watching the jets land through dark-tinted glasses. He greeted Dellentash with a firm handshake and introduced himself as “Steve Teri.” He described himself on the telephone as a real estate developer, keen to talk business with the high-flying New Yorker from the pages of People.

Walking into a private room in his sprawling office, Steve said, “Listen, you’ve got the perfect setup. I need a plane to go to Pakistan.”

“Please sit down,” he added. “I need you to pick up some drugs.”

“The propeller disaster in Belize was fresh in my mind,” Dellentash says, “but everything with this guy just seemed organized. He made it all sound easy. He offered $150,000 in start-up money, so he was really talking my language.” But as Dellentash would discover, this gentleman’s name was not Steve Teri, and he was no realtor.

Dellentash decided to give the smuggling game another try and excitedly flew his Convair back to Stewart Airport in New York. But Charles Braunstein was waiting. FAA agents forced their way inside the cockpit and cited Dellentash for illegally operating an airline. With no foreign diplomats on board to protect him, Braunstein delivered a $770,000 fine and grounded the aircraft. This was the part of the job he loved — taking the keys. But Dellentash calmly asked a stewardess to fetch his briefcase, and minutes later, Braunstein watched the Convair roar into the skies again as he stood gripping a certified check for $78,000, the exact amount of the fine’s “payable.”

Despite Steve’s promises, the Pakistan job was a bust: When Dellentash arrived at the meeting point near Islamabad, armed Pakistani gangsters were engaged in shootout in a hotel lobby. Fleeing in a hail of gunfire, Dellentash escaped back to the States. Then Steve persuaded him to try a similar job in Colombia to recoup their money. Again, he promised it would be easy. He was a hard guy to turn down.

Dellentash took his old Oklahoman buddy Lenny as a co-pilot, for his experience and cool nature behind the controls. Though the pick-up in Colombia was stress-free, they didn’t take enough gas and barely made it back home. “I remember flying over the theme park in Orlando, and I could see the fairytale castle all lit up, and I was flat out of gas with a cargo hold full of drugs,” says Dellentash. “I was flying all over the place, thinking it was the end. We were gonna crash land with thousands of pounds of marijuana.” They searched for the promised buckets of fire. “I was making so much noise it was unbelievable,” he says. “I was coming in hot, but I said, ‘Fuck it, I gotta land this thing, or it’s gonna land me.’”

As the plane fell into a controlled descent, he flipped on the lights as they smashed into a farmer’s field. “Before that night I never thought a cow could have an expression,” he laughs, “but they were scared!” The aircraft skidded into the mud. Dellentash shut down the engine and waited for the sound of trucks. Steve’s gang was quickly on hand to load up the drugs. Then a watchman ordered to fire a warning shot gave the signal that cops had arrived. The trigger-happy cops returned fire.

Dellentash ducked as the unmistakable BING! BING! BONG! of rounds struck the plane. The cockpit window exploded. “They’re shooting at us!” he screamed, and they ran into the dark night.

* * *

Steve was furious. If he had been there, he said, the FBI would have busted him. He told Dellentash that his real name was Salvatore Ruggiero, the younger brother of the fearsome gangster Angelo Ruggiero, and the ringleader of New York’s Pleasant Avenue Connection drug ring, a forerunner to the legendary Pizza Connection. “I’m the most wanted man by the DEA,” he confessed. The mobster was desperate to earn his $250,000 back from the failed missions. “The problem is your guys,” Dellentash suggested. “Respectfully, I want to keep you out of it. You give me the Colombian contacts, I’ll make the pick-up and deliver it to New York. I’ll make it like Federal Express … for drugs!”

Steve, or Salvatore, invited Dellentash to a restaurant in Miami Beach. At midnight a Colombian walked in with two girls on each arm. “He was one of the best-looking guys I ever saw,” says Dellentash. “And the girls he was with? I wanted to pinch them to make sure they were real.” That man was Carlos Lehder, who revolutionized the cocaine industry and teamed up with American smuggler George Jung, making millions of dollars and winning the trust of the biggest suppliers of cocaine in Columbia: Pablo Escobar and his Medellín Cartel. Lehder gripped Dellentash’s hand and looked him in the eye.

Later, at one of Salvatore’s pork stores in Fort Lauderdale, the three men talked as their breath hung in the chilled air. “Here’s another fifty for expenses — now can you not fuck this up?” Salvatore joked as he handed Dellentash a tinfoil package of cash. Dellentash was in business with the mob.

Braunstein was waiting as he taxied down the runway at Stewart Airport in New York one day in 1980. “You’re running an illegal airline and this time we are confiscating your aircraft, Dellentash,” he said, but the pilot pushed past him towards a waiting limousine. Dellentash wound down the mirrored window and tossed him the keys. “You can keep the damned thing,” he said with a smile, as the car slid away. “I got others.”

* * *

Dellentash and I are eating at a diner in Studio City, California. Sly Stallone is holding court five tables down, but the waitresses fuss over Dellentash, mainly because he tips roughly 200%. Over eggs, Dellentash says he would rather talk about his rock music achievements. In around 1980, his rock star passengers introduced him to the famous music attorney David Sonenberg, who asked if Dellentash would like to co-manage Meat Loaf. His first client was one of the record industry’s most successful, and troublesome, talents. “I was delighted, but I felt like being in a pressure cooker,” says Dellentash. “I was living my dream, to become a big player in the music business. Meat Loaf had the talent, and he had the songs. Meat Loaf’s only problem was he looked like Meat Loaf.”

“The music biz was clearly a sideline for Al,” Meat Loaf wrote in his 2000 autobiography. “He would tell these stories about flying to Libya with a load of automatic weapons. It was enough to make me afraid of him. One day Dellentash came into the studio. He’d bought in a shoebox wrapped in tinfoil. I opened it expecting to see cookies. When I took the tinfoil off I saw it was full of hundred-dollar bills. Wrapped like in the movies, with the little seal around them… I said, ‘Whoa,’ and wrapped it again fast.”

Together, Sonenberg and Dellentash wrangled cash advances from record companies for Meat Loaf albums, tours and movies. Dellentash brought street charm and muscle to the bargaining table; Sonenberg crunched the numbers. That year, Dellentash helped the Bay City Rollers sell an album to CBS International for $250,000; he hung out with Jimmy Iovine, who would later go on to form Interscope Records and the Beats by Dre headphones empire. Meanwhile, his airplane business attracted huge clients like OPM, the crooked computer leasing business that stole $225 million from various banks and guru Shri Hans Ji Maharaj, the leader of the questionable religious sect The Divine Light. They were all attracted to Dellentash — and the vast riches he was accumulating.

Dellentash purchased a lavish headquarters on Riverside Drive in New York City and furnished it with Louis XIV furniture. The lobby was dressed entirely in gold and paneled in rich mahogany. There was even a pink room with a pink grand piano at the center. “I had a private chef, and a full-time guy just to keep the fireplaces roaring at all times and a theater room with a twenty-foot screen,” he says. “We’d host sex parties with all the best girls.” Dellentash was now dressed to kill, wearing $400 shirts and shoes made from exotic animals. He employed a former college linebacker for a bodyguard who had twenty-one-inch biceps and reveled in his nickname, “The Brick.”

Dellentash started to become tempted by the beautiful women who populated the music industry, the girls befitting of his new status as one of New York’s rising stars. One spring day in 1980, he held a casting for a Meat Loaf video called “Read ’Em and Weep.” The last girl arrived wearing killer high-heels and a tight pantsuit.

Bonnie was a waitress at the Playboy nightclub on East 59th Street, the imposing nine-story building that boasted over 38,000 square feet of adult fun. To her delight, Bonnie found the Playboy job also came with a host of perks: She launched a submarine in Groton and played baseball with the Navy Seals. When the music business required attractive girls, they knew Playboy bunnies were available.

“I immediately fell for her, the moment she walked in the door,” says Dellentash. At the casting call, Bonnie waited in the doorway with her hands on her hips. Dellentash’s full-time fire-tender, distracted by the blonde, nearly let the flames go out.

“She was drop-dead gorgeous,” says Dellentash. “But she knew it!”

Dellentash with Bonnie, twenty-two at the time.
Dellentash with Bonnie, twenty-two at the time.

“His office was ridiculous,” Bonnie tells me. “He sat behind a twenty-five-foot desk, and his chair was an airplane seat. It even had a safety buckle! I just saw this huge ego. He asked me out, but I said no way.”

Somehow Dellentash convinced her to fly on his private jet to watch another of his artists, Southside Johnny and the Asbury Jukes, play a sell-out concert at the Blossom Music Center in Cleveland, Ohio. Afterwards, he let her take the controls and they listened to Blondie records as they soared through the clouds, back to his ludicrously appointed residence overlooking Central Park. That night she slept on his sofa and was gone before he awoke. With her blue-collar upbringing and street smarts, Bonnie was more than just a match for Dellentash: She was a challenge. At the time he had the pick of almost every woman in New York, and naturally, he desired the one he couldn’t have.

“Chasing Bonnie had become a full-time job,” Dellentash recalls. But a second date turned into a third, and soon she had moved into his apartment. Dellentash was still married but says his heart already belonged to Bonnie. She was more than a lover; she was a co-pilot.

* * *

The twin islands of Little and Great Inagua are the bird-watching capital of the Bahamas. More than 80,000 pink West Indian flamingos reside there, but that’s not what drew Dellentash to the islands. The coral surrounding Inagua made it inaccessible to Cuban smugglers in speedboats, granting an opportunity to a drugs pilot.

At the pork store meeting, Carlos Lehder enthused to Dellentash about the potential for the Bahamas as a drug transshipment point. He had arrived in nearby Norman’s Cay in 1978, buying up large pieces of property, including a home for himself known as The Volcano and an airstrip. Dellentash knew he had a lot of work to do: “Do you know how hard it is to corrupt an entire island?” he laughs while recounting the story.

Dellentash decided to arrive in flamboyant style: He performed a loop-de-loop when he landed in Nassau and hired the best bungalow at the best hotel on the island, bringing Bonnie under the guise of a island vacation. “When we arrived there were pink sheets, pink pillows and the walls were decorated pink,” recalls Bonnie. “There was even pink toilet paper. He’d hired a Bahamian guitar player to play ‘Love on the Rocks’ for me, by Neil Diamond, but calypso style.”

“The worst fucking guitar player in history,” says Dellentash.

But there was business to do: He had to set up one of the most effective drug routes in history. The first few missions were a dream, he says. Dellentash and Lenny flew down to the Bahamas from Florida and refueled at Inagua. They took with them $40,000 in cash — $15,000 for the Bahamian military, $15,000 for customs and $5,000 for fuel. Soldiers would guard the plane all night from the prying eyes of the DEA or rival Cuban smugglers.

At five a.m. they took off from Inagua, and within hours they were flying over the jungles of Colombia. “You’d be looking for a guy on a tractor waving a red handkerchief,” recalls Dellentash. Out of the woods, a tractor arrived carrying 5,000 pounds of weed.

Back in Inagua, the military stood guard over the plane again as they refueled, then departed for Millville, New Jersey, where he used large hangars that served as ammunition dumps during the Second World War and replaced the padlocks with his own.

“I basically had my own airport,” says Dellentash.

That’s not to say the drug route wasn’t difficult or dangerous. Dellentash avoided the obvious routes into Miami and Jacksonville by flying into Cape Hatteras, a tempestuous strip of North Carolina coastline known to sailors and pilots as the “graveyard of the Atlantic.” There, deadly currents create countless shipwrecks, and few pilots dare to fly during storms. But these were the perfect conditions for “flying dead” through the night — with no lights or navigation, invisible to the authorities.

He remembers his cockpit illuminated with St. Elmo’s Fire, the mystical phenomenon that creates a halo of bright electricity around an aircraft. To some it was an omen of death, but to Dellentash it was just plain beautiful. Lights on the coastline twinkled out of the dark as he pulled the yoke, dropping even closer to sea level. At just a hundred feet above the water, sometimes a ghostly ship appeared through the sea mist, passing his wing by meters. He flew so low that the cold waves often sprayed the plane with seawater.

On board was 10,000 pounds of high-class marijuana wrapped in gabardine bags, with a street value of a million dollars. One night, his gas needle was flat-out dead as Kill Devil Hills loomed nearer. Named after smuggler-talk for rum, this was contraband county, and under the port side, black waters gave way to emerald green hills. At an unmanned Carolina airport he suddenly soared towards the heavens — a fake takeoff, designed to fool air traffic control to think he was domestic traffic. Often, Lenny was directly above him in an identical Cessna: “Double the load for just one radar blip,” he explains. But even with long-distance gas tanks, sometimes they only just made it home.

Under the cover of darkness, they unloaded the pot in Millville. Passenger seats were loaded into the Cessna and marijuana leaves vacuumed away. Then their truck wound its way up the New Jersey Turnpike into the city. A “smash” car followed: If cops pulled the van over, the back-up driver would deliberately crash into the cops and take off. He never needed it, Dellentash says. But it paid to be organized.

Dellentash relaxes with Bonnie in the Bahamas. At this time, he was one of Pablo Escobar's personal pilots, and a partner of the notorious crime boss Salvatore Ruggiero.
Dellentash relaxes with Bonnie in the Bahamas. At this time, he was one of Pablo Escobar’s personal pilots, and a partner of the notorious crime boss Salvatore Ruggiero.

Between 1979 and 1982, Alfred Dellentash imported millions of dollars of Pablo Escobar’s cannabis and cocaine directly into New York, riding a wave of crime that changed the very fabric of American life. His cover made him absolutely bulletproof: By day he was a rock ’n’ roll impresario in the studio with chart-topping acts, by night he was hiding seven million dollars in cash behind fake walls in his home.

When he speaks of this era, Dellentash talks fast, and continuously adds “in the interim,” as a way to cycle between the worlds orbiting his gravitational pull: planes, rock stars, drugs and Bonnie. “Keeping all the plates spinning was becoming impossible,” he says.

Bonnie and Dellentash were hitting the town every night: Studio 54, Underground, Savoy Club and the Ritz, laughing like teenagers in the back of limousines. “People were falling over themselves to let us into the clubs,” Bonnie recalls. “He was a celebrity.” Champagne flowed, flakes of pure cocaine were pushed into long rails. His fame soared.

But cracks were appearing. The Meat Loaf movie was a flop: “Dead Ringer” “barely made sense,” a reviewer wrote in The New York Times. Dellentash spread himself too thin, and while Bonnie had just a small part in the movie, she had taken over the second lead role in Dellentash’s life. That’s not to say he was always truthful: One night Bonnie walked into a restaurant and spotted him dining when he was supposed to be in the Bahamas.

“You said you were in the islands!” she yelled, throwing a drink.

“I am!” said Dellentash, soaked in a cosmopolitan. “Long Island!”

* * *

Bodies started turning up in the Bahamas. A yacht belonging to a retired couple was found drifting near Norman’s Cay. Carlos Lehder was thought to be behind it. “The Bahamians got greedy,” says Dellentash. “Inagua was no longer low-key — you had to line up behind twelve other drug planes to take off,” he says. “The bunk house where we slept looked like that canteen in ‘Star Wars’ — everyone had guns and was doing blow all night.”

President Reagan was now in power, struggling to dig America out from under a new recession. And Salvatore Ruggiero, now earning huge profits from the scheme, tried to interest Dellentash in the heroin industry by giving him a sample. Dellentash arranged for two known junkies to test its quality; both immediately overdosed and were taken to the hospital.

Then, during a party in Manhattan, a fashion model accidentally snorted that heroin, “Pulp Fiction”-style, by confusing the powder with cocaine and collapsed during sex with one of Dellentash’s gang. “I thought I had a body on my hands,” says Dellentash. “I finally bought her around by thumping her chest. I was screaming at her, ‘I ain’t going to jail because of you!’” Heroin was a curse, Dellentash says, and he vowed to avoid it at all costs. “The mob were not supposed to be involved in drugs. The Gambino family prohibited it,” he says. By the spring of 1981, the matter had driven a rift between him and Salvatore.

“We’re going into the heroin business,” enthused Salvatore.

“The problem with heroin is your brother’s involved,” said Dellentash. “And you always said getting involved with your brother is the road to the end.”

In a ferocious argument, Salvatore ordered Dellentash to gear down his music business and concentrate on importing heroin from the Golden Triangle, the infamous drug-producing region spanning Northern Thailand, Laos and Myanmar. But Dellentash was on the brink of making record-label history. He says he was working with an unknown teenager named Jon Bon Jovi, a kid he believed would become a star. Dellentash wanted out of drugs altogether. Then Salvatore threatened him: “That little blonde girl of yours,” he said, “she’s a distraction. Do we need to remove her from the situation?”

Bonnie was blissfully unaware of Dellentash’s moonlighting. She had met “Steve Teri” once and hated him. By now, Dellentash had got her out of the Playboy Club and into fashion school, but she was pressuring him to settle down. He kept on promising “tomorrow.”

“I never felt like the other woman,” Bonnie says. “I was always the number one.”

Salvatore demanded a meeting and told Dellentash to send a plane to bring him from New York to his Florida headquarters for a sit-down. The Gates Learjet 23 was a favorite of Dellentash’s because it had the call sign N100-TA, which he jokes stood for “Tits and Ass.” It took off as planned at 11:35 a.m. on May 6, 1981, from Teterboro airport, climbing to 24,000 feet at a rate of 300 knots. The pilot was informed it was a perfect day for flying, and on board he was joined by a co-pilot and just two passengers, Salvatore Ruggiero and his wife.

“Descend to maintain flight level three nine zero,” came the call from air traffic control, and the pilot duly acknowledged, stabilizing her at 39,000 feet. But one minute and thirty-two seconds later, the co-pilot hurriedly reported that the plane was going down. In the background, air traffic control overheard a warning horn. The plane was in free-fall. It made another transmission, but air traffic control could not understand it.

Dellentash's infamous Learjet, number N100TA, or "tits and ass," as it came to be known, on the tarmac at Teterboro Airport in New Jersey.
Dellentash’s infamous Learjet, number N100TA, or “tits and ass,” as it came to be known, on the tarmac at Teterboro Airport in New Jersey.

“Say again,” said air traffic control. “Say again.”

A passing fishing boat found the wreckage of the interior of a fancy jet, and told authorities of sharks eating the bodies. Dellentash was in the studio when the phone rang.

“I thought you were dead,” said Agent Charles Braunstein. Dellentash pulled down the volume lever on the mixing deck. He swung his chair away from Sonenberg and held the phone closer to his ear.

“Did you know your Learjet just crashed off Savannah, Georgia?”


“Your Learjet just crashed. Who was on board, Al?”

“Must have been a charter.”

“Who was on board?”

Dellentash paused.

“My friend Steve Teri and his wife.”

* * *

The FBI was already listening when Dellentash called Angelo Ruggiero, Salvatore’s brother, with the bad news. Agents disguised as construction workers planted listening devices in Angelo’s kitchen, dining room and even bugged the princess phone in his daughter’s bedroom.

“This is Angelo,” said the voice.

“It’s me,” said Dellentash. “The brother’s dead.”

There was a pause.

“Who killed him?”

“No one. He crashed in my plane this morning. I swear to God.”

“What did you say?”

FBI Agents later heard how difficult it was for Angelo to accept his brother’s death because the body was in “fuckin’ pieces.” Angelo said: “If Sal would have been shot in the head and they found him in the streets — that’s part of our life, I could accept that.”

“Listen, I’ve got guys on my back,” Dellentash told Angelo. “I got his assets, he’s been living in my house and we’re one day away from the Feds being here. I’m gonna have to tell them it was him on board. Okay? We need to clean house.”

“Where’s the heroin?” Angelo demanded.

“I don’t touch heroin.”

“Listen, whoever has this heroin,” said Angelo, “I’m gonna put a shark in my pool, and I’m gonna feed that guy to a shark like a spaghetti dinner.” Dellentash put the phone down, and went cold. Just a moment ago he had an empire, a music career and a future with Bonnie. Now, he was looking at decades in jail, or worse: death.

After all, he knew Salvatore’s heroin was stashed at his home.

* * *

The death of Salvatore Ruggiero set off a chain of events that would create an internal war within the Gambino Family and eventually lead to the crowning of John Gotti as its leader. It also drove a rift between Dellentash and Bonnie. Shortly after the crash, the FBI wrote to Bonnie to inform her that her phone had been tapped. Naturally, she demanded answers.

“I want my own life,” she told him.

On a good night as a waitress at a comedy club in the city, Bonnie was now earning $1,500. She told Dellentash he could have been just a big success without all the schemes and cons. She was an honest girl from a good family and didn’t deserve all this. They split, and, heart-broken, he fled to his winter home in Vermont to clear his head. But his phone didn’t stop ringing.

“I got serious problems, Al, I’m in a fix,” said Lenny.

“I told you I’m on vacation. Call me after Christmas, Lenny.”

“They might take my life, Al. I might not be around next year.”

Lenny said he needed money to get him out of trouble. He said he owed a connection in Louisiana some cash for a cocaine deal, and Dellentash was the only guy he could trust to help.

“How much do you need?” asked Dellentash.

“Two hundred and fifty.”

Dellentash saw an opportunity. “What if I gave you a hundred and fifty, and enough heroin to hold on to as collateral?” he said, eager to get rid of the stuff. Dellentash never liked bringing cash and drugs together in the same place, because it increased the risk for all parties involved. But he could help Lenny and himself, so he agreed to drive to a hotel in Louisiana.

Two men knocked on the door of room 12, and Dellentash let them in. One was tall, black, with prison tattoos and earrings. “The other guy was a nervous junkie,” says Dellentash. “The whole situation stunk. I was gonna get rolled, and I knew it.”

Dellentash pulled his gun, but the door crashed in and twenty guys appeared. A shotgun butt smashed into Dellentash’s jaw, knocking out five teeth. The gun flew out of his hand, and his mouth poured with blood as he staggered to his feet. Another punch floored him. “I was certain they were gonna kill me right there,” he says. “Then they started screaming, ‘Police!’”

“I was relieved!” admits Dellentash. “I thought it was a take-down. I thought I was gonna get killed.” In handcuffs, Dellentash figured it all out. Lenny had been busted, he figured, and turned him in for a lighter sentence. He watched a cop take $10,000 from his stash and hand it to the two crooks. “It was a total setup,” he says.

From East Baton Rouge police station, Dellentash was taken to the local jail and locked up alone. He was charged with criminal conspiracy to distribute heroin and firearms offenses. They allowed him just one five-minute telephone call, and it was a miracle Bonnie picked up. “It’s me. I’m locked up in a dungeon — I’m in federal. Just tell everyone I’m okay.” he said. The money ran out just before he added: “I love you.”

“I thought he could beat anything,” Bonnie tells me. “The arrest made me realize I couldn’t imagine life without Al. He just… got me. He understood me. No other man did. Al didn’t need money or planes to win me. He thought he did, but he didn’t.”

Dellentash was arraigned to appear in Baton Rouge state court. The judge was an elderly Southern gentleman who ordered Dellentash to stand and make his plea.

“Not guilty,” he said, defiantly.

The judge sighed and slowly put on his spectacles.

“You’re from the north, I believe?”

“Yes, sir. New Jersey.”

“Well let me explain in terms you’ll understand. Imagine you are at a barbecue,” he said, as sniggers broke out among the clerks, “and you’re the chicken.”

* * *

Jack Dampf was a popular Baton Rouge defense attorney who had practiced law in the area for eight years. He was thirty-four and kept a busy office thanks to his captivating turn of phrase in the courtroom. He was expensive, Dellentash recalls, but worth every penny.

“I thought Dellentash was toast,” Dampf told me on the telephone. “The cops tested a sample of the heroin he was holding in their lab, and they had never seen anything quite like it. I mean, it was off-the-scale pure. They knew just by the purity of the heroin that Dellentash was involved incredibly high up the chain — or he was Mafia.”

Dampf says he was summoned to a confidential room in the U.S. attorney’s office, where he met a group of Organized Crime Strike Force officers from Chicago and New York. The officers showed him black-and-white photos of Dellentash with various celebrities. “There was Dellentash with organized crime figures, rock stars, and I think I saw one with Frank Sinatra. I was taken aback,” says Dampf.

“He is a very well-known person,” the officers explained. “He’s part of an organized crime gang.”

“And there I was thinking he was toast,” says Dampf.

That night, Bonnie held his hand in the prison visiting room, where they sat among the terrorists, arms dealers, their wives and children.

“You’ll work it out. If anyone can dodge this, you can,” she said.

Dampf pushed for a proffer, an agreement that allows a person under criminal investigation to provide information about crimes with assurances of protection against prosecution. Dampf requested total immunity for his client, because testifying about organized crime and drugs would mean signing his death warrant. And though it broke his heart, Dellentash told Bonnie, “You can date other people, you know. You can’t wait around for me. I’m gonna be gone a long time.”

Gotti’s Racketeer Influenced and Corrupt Organizations Act (RICO) trial began in August 1986, with the prosecution relying heavily on testimony by convicted felons. “I had to stand there and give my evidence, and the courtroom was packed with wiseguys, staring straight at me,” says Dellentash. Dressed in their Sunday best were John Gotti, Gene Gotti and their crew. In the gallery, Dellentash says he saw one thug mime the unloading of a pump action shotgun in his direction.

The trial was a farce. One witness committed perjury by accusing the prosecution of offering him drugs in prison in return for testimony, while other witnesses admitted that their testimony was buying them shorter sentences. After a long and rancorous trial in which the defense repeatedly traded personal slurs with the prosecutors, Gotti was acquitted in March of 1987.

Dellentash received fifteen years for conspiracy to distribute heroin and ten years for possession of felony weapons. His wife divorced him as he languished in a high-security jail where he paced an isolation cell in his underwear. Bonnie reluctantly moved on. After he was released in July 1988, having served just five years, Dellentash tried to make a new life for himself. He ran a restaurant in Rutland, Vermont, before a federal agent tipped off a journalist who wrote the front-page headline: “Mob Man in Mendon.” But all he really wanted was to get Bonnie back.

“She slammed the door on my face whenever I called,” he says. Though her heart was elsewhere, Bonnie tells me she could never forget about Dellentash: “I’d listen to the radio, and every song would remind me of Al.”

When Bonnie was rushed to the hospital with acute stomach pains in 1988, doctors thought it was life-threatening. A mutual friend told Dellentash, who ran to the hospital. “Seeing him there was magical,” Bonnie tells me. Though it was only a burst appendix, the drama reunited the couple. “You can’t help how your heart feels,” she says. Bonnie agreed to take him back, if he quit his hustling for good.

“You’ve got to have a real life now,” she told him.

“I don’t even know what a real life is,” Dellentash said.

And then one day he woke up and she had run away to California without leaving a note. Dellentash followed her.

“I booked the first ticket out of New York. One way. I had no money left and I had no idea what I was going to do,” he says.

“Luckily he brought only his good side to California,” Bonnie says. “He left the bad guy back East.”

Dellentash with Bonnie at their house in the Bahamas at the height of his drug-importation success.
Dellentash with Bonnie at their house in the Bahamas at the height of his drug-importation success.

* * *

Our last interview takes place at a busy chain restaurant in a shopping mall in Los Angeles. Bonnie is here too, and she is beautiful and fun. She tells the stories better than Dellentash. It is a Friday night, and there are cocktails — Dellentash is in a reflective mood. He finally tells the truth about his motivations for telling his story: He is in remission from stage-four cancer. But this is a now-or-never mea culpa.

He concludes that he spent his life on the run, and his pursuits all followed a common theme: Escape. There were planes, drugs and rock ’n’ roll, but they were all just means of getting higher, faster and richer than the rest. He ran from the domestic boredom of New Rochelle, becoming a modern-day Peter Pan: He refused to grow up and instead flew to mysterious islands, battled pirates, lost his Wendy.

“I stopped running when I took a job as a car salesman,” he says, “being told how to sell a car by a teenager.” Of course the phone still rang: Would he like to produce a rap record? Hire some planes for a trip to Colombia? Move some goods to the Midwest? But all this would mean losing Bonnie.

His supervisors watched with wonder as this mysterious East Coast transplant made sale after sale, quickly becoming one of the area’s best sales managers. Now he mentors young salesmen with criminal pasts. When he married Bonnie they filled a pretty suburban home with nice furniture and had two kids, now grown up. What he was running from all that time turned out to be the very thing that made him feel so complete.

“The prosecutor in the Gotti case said that it was suspicious how Salvatore died in my plane,” says Dellentash. I suggest it was a hell of a coincidence, to which he responds: “If I killed one of the Gambino guys, then testified against Gotti, do you think I’d be sitting here eating dinner with you?”

Whatever the truth is, he still prefers to sit where he can see the door.

The waitress hovers, refilling his coffee after almost every sip, it seems. He takes a bite of his omelet and says, “I’m living a second chance.”

* * *

Liked this story? Our editors did too, voting it one of our 20 best untold tales!

See the complete list of Editors’ Picks here. 

* *

Jeff Maysh, thirty-two, is an investigative journalist based in Los Angeles. His bylines include the BBC, the Guardian, Vanity Fair and the New York Post.

Naomi Elliott is an illustrator living and working in London but dreaming of New York.

*Some names have been changed at the request of the interviewees.