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How Derek Oatis went from a teenage outsider to private school drug kingpin

Jabberwocky

Frumious Bandersnatch
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Nov 3, 1999
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DEREK Oatis’ plane touched down at New York’s John F. Kennedy International Airport at 1.35pm.

The night before, the 17-year-old was sitting, scared, in a Venezuelan hotel room handing over $5000 to three men with guns in exchange for 350 grams of cocaine.

Like the other times before, he hid most of the coke in a bottle of baby powder, stuffed the rest of the baggies in his pockets and headed back to the US with his girlfriend.

The plan was to distribute the drugs to his classmates at Choate Rosemary Hall School in Connecticut — one of the most elite private schools in America. With John F. Kennedy, Ivanka Trump and Michael Douglas among its alumni, it’s the kind of school where it’s considered strange to not have your own private helicopter.

When Oatis’ flight landed at JFK, he was nabbed by two law enforcement officials. They found the cocaine in his pockets and in the baby powder — federal officials estimating its street value to be $300,000.

“My heart came up into my throat. I knew that the whole charade was over,” Oatis told 60 Minutes in 1984, a few months after he was arrested.

Thirty years later, Oatis’ story serves as the inspiration for The Preppie Connection, which hit screens in the US this month. Thomas Mann stars as Tobias Hammel, based on Oatis, and Australian actress Lucy Fry plays his girlfriend, Alexis Hayes.

“He had an incredible will and an ability to manifest things,” director Joseph Castelo told news.com.au of Oatis, who he first contacted a decade ago.

IT JUST KEPT GROWING

Oatis was unpopular and his life certainly didn’t match those of his peers. They were rich, he was not. They were from old-money families with fancy cars. His mother was a public school teacher and his step-dad a vending machine delivery man who drove a banged-up Dodge Dart.

“My mum was very motivated in trying to get me the best education possible,” Oatis told Newsweek. “She went to Southern Connecticut State University, and she’d drive by Choate and say, ‘Geez, it’d be amazing to have my child go to the same school JFK went to’.”

Excelling academically without really trying, Oatis applied to Choate and was accepted on a scholarship. He became friends with Matthew Holmes in his sophomore year, their outsider statuses drawing the boys together.

But things changed when Holmes visited his parents in Venezuela and brought some marijuana back to school. It snowballed, and soon he was smuggling small amounts of cocaine back. Suddenly, he and Oatis fitted in.

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“He was a bit like I was: sort of awkward, insecure, not very popular,” Oatis told the New York Post about Holmes “So when he started bringing back stuff and people took notice, he was probably motivated by the same motivations I had.

Fitting in, being the big man on campus.”

Holmes smuggled cocaine back to school five times before he invited Oatis to come to Venezuela with him for spring break in March 1984. Scoring 200 grams, they hid the coke in a bottle of baby powder and Oatis offered to carry it on the flight back to the US.

“I felt I owed him,” Oatis told Newsweek. “I hadn’t paid for anything. And I did — I brought it back without any incident whatsoever.”

The teenage thrill and the popularity that came with it was addictive. And so was the drug.

“The first time I did it was with Matt and some folks, and I felt like hell,” he told the New York Post. “My heart was going a mile a minute, and I couldn’t sleep. But the next day, I wanted to do it again.”

He became more popular around the dorms. He knew he was getting in deeper, but he couldn’t stop.

“There was a certain quality Derek had,” said The Preppie Connection director Joseph Castelo. “It almost felt like there was a gravitational pull on his character. He knew what he was doing was going to destroy himself but he was pulled and he couldn’t stop.

“He often described that it just kept growing and growing and he couldn’t stop it even though he knew he could stop it.”
SCARED SH*TLESS

Six weeks after scoring the 200 grams, Oatis offered to make another run to Venezuela with his girlfriend, Catherine Cowan. Offering to bring back coke for whoever wanted it, he collected $5000 from Choate students and set off, using Holmes’ connections.

In their Caracas hotel room, at about 10pm, there was a knock at the door. Three dealers with guns.

“I was scared sh*tless,” Oatis told the New York Post. “It was one dude who looked like something out of a bad movie. He had a bad accent, a long black moustache, and there was a guy on each side of him, with automatic weapons under their jackets.”

Oatis handed over the $5000 and the men pulled out 350 grams of cocaine wrapped in plastic.

During the 45 second exchange, he says he realised he’d be lucky if he escaped alive.

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CHECK THE GARBAGE

Heading back into the US, on April 23, Oatis hid some of the cocaine in an innocent bottle of baby powder and stuffed the rest of the bags into his pockets. It worked before.

During the flight, he had a window to change his mind.

“When he was on the plane, he had the opportunity to dump the cocaine and he didn’t,” Castelo said. “Like a true archetypal tragic hero, he had the opportunity to hit the reset button on the story, and he didn’t do it.”

Their flight landed at JFK and as Oatis and his girlfriend walked through the airport, they were stopped by two law enforcement officials. Hauled into a private room and searched, the officers found the baby powder.

“They sniffed it and dumped it into the garbage — there was a little baby powder at the top, so it looked like baby powder,” Oatis told Newsweek. Continuing the search, they found the baggies he’d stuffed in his pockets and asked where the rest of it was.

“I was stupid enough to say, ‘You just dumped it in the garbage’.”

He was taken to jail and faced up to 15 years in prison.

At first, the bust was chalked up to being the result of a “random inspection of passengers”, but the school administration later admitted to tipping off the authorities after a teacher reportedly informed the faculty.

“I’ve always thought of myself as a good person, but no matter what I thought, I know I’m capable of doing terrible things,” he told the court at his sentencing.

The judge sentenced him to just five years’ probation and 5000 hours of community service. Cowan received three years of probation and 1000 hours of community service. They were both expelled from Choate, along with the 12 students who gave them money for cocaine.

For some people, it would be enough to ruin their life. But for Oatis, the thrill and downfall of his senior year seems to be just a small blip in his life. Now 49, he practices criminal law in Connecticut and is a prominent animal rights activist.

“I think he has tremendous regret over what happened,” Castelo said. “I know he’s expressed that he’s sorry for the hurt he caused his mother. But he also told me it was a wild time of his life and he had a lot of fun. There was something exciting about it as well.

“But obviously you can chalk that up to youthful ignorance. He was walking on that edge.”

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Source: http://www.news.com.au/entertainmen...n/news-story/8a7c09d3b1d21a79a5637ca8082958cb
 
People don't just use drugs because they're "youthful" and "ignorant". It's largely built into our nature to seek altered states of mind.
 
LOL Choaties

If they knew more townies they wouldn't need to go much off campus to find drugs
 
That is funny i know exactly where this is... happy to say im from a much cooler and more hard area though from the "other side of the tracks"

Have you been to the campus?

I live within walking distance, so I've run/walked/driven through hundreds of times. They've got a nice track and they do let the town use some of their soccer fields for youth town soccer leagues. Maybe some other fields as well. They did let my high school use it's indoor track to train on in the winter a few years ago, so they do help out the townspeople, but there is a sort of townies vs. choaties rivalry. The campus has a pretty good hill for sledding in the winter. And if you look high school age you can walk into the Student Activity Center (SAC) and play air hockey/ping pong/foosball, etc. Though they probably have tighter security now than they did 10 years ago.

They have a public outdoor symphony orchestra that plays on campus during the summer. It's really enjoyable actually.

The "rivalry" is pretty much based on BS. The biggest annoyance seems to be that if driving by during class change Choaties don't seem to be very good at looking both ways before crossing the street, especially considering their high academic standards.
 
Have you been to the campus?

Actually I have not. When I say "the other side of the tracks" I mean like 2 towns over. The most experience i have is with the road crossings LOL Out door orchestras sound cool though, if only i didnt look as old as i am :(
 
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