The life of Derek Oatis changed forever on April 23, 1984, when he was a 17-year-old senior at the prestigious Wallingford, CT prep school, Choate Rosemary Hall. On that date, he was busted with more than a pound of Venezuelan cocaine at JFK Airport, which he intended to deliver to classmates. He and others were expelled from the school, but Oatis’ punishment of five years in prison was much harsher. He had smuggled about $300,000 worth of coke from Venezuela during his run. Now a UConn-educated lawyer with his own firm, Oatis’ story will be coming to the big screen on Friday, in the film The Preppie Connection.
Oatis, the son of a public school teacher mother and truck driving father, wasn’t like his classmates at Choate. While they arrived at the alma mater of John F. Kennedy, Ivanka Trump and Michael Douglas, in luxury cars (some of their parents came arrived in helicopters), Oatis (who attended Choates on scholarship) was dropped off in his parents’ rusted Dodge Dart. When he tried to scoop one of his female classmates, another boy pulled her from him, by offering her a skiing trip in Colorado via helicopter.
During his sophomore year, Oatis befriended another social misfit named Matthew R. Holmes. Holmes’ parents lived in Venezuela, and he would return from South America with weed to dispense among their party-hearty classmates. “He was a bit like I was: sort of awkward, insecure, not very popular,” Oatis told the NY Post. “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.”
Soon, students started asking Holmes if he could get his hands on cocaine, which was plentiful and cheap in Venezuela. He
started bringing some blow back with him from his trips. The feds say he made at least six trips of this kind. Oatis joined his friend on one of these trips in March 1984, to get some coke to use and share with others. “The first time I did it was with Matt and some folks, and I felt like hell. My heart was going a mile a minute, and I couldn’t sleep,” said Oatis. “But the next day, I wanted to do it again.” The smuggling chums grew in popularity at Choate.
In April of that year, Oatis decided to make a run on his own and use Holmes’s plug to bring back work. He spread the word and pooled $5,000 from his fellow students to cop with. Oatis flew to Caracas with his girlfriend, Cathy Cowan, and checked into a local hotel. That night, Three dealers, toting automatic weapons, came through. In about 45 seconds, a shook Oatis exchanged his cash for the drugs, with minimal conversation. Oatis and Cowan boarded a plane back to the US the next day.
As the couple walked through JFK, they were intercepted by the laws and taken to private room to be searched. He had close to a pound of coke stashed in a baby powder bottle. In an amateurish maneuver, since all of his load didn’t fit in the bottle, he had simply bagged up the rest and put the baggies in his pockets. Though the cops said that their search of Oatis was random, it was not. Oatis was reckless in his dealings and a hip teacher found out and dropped a dime on him.
Oatis was spared 15 years in the slammer, and the judge sentenced him to five years and 5,000 hours of community service. Oatis reflected, “We were a white family, and I hate to say it, but that helped in our fortunes.”
His lady was sentenced to three years of probation and 1,000 hours of community service. The 12 students who funded the fateful mission were expelled from Choate, but were able to live fruitful lives in “prestigious industries,” such as finance. One of the 12, Chris Vlasto, is now an executive producer for Good Morning America.
The Preppie Connection is due in theaters and on demand on Friday (March 18). The Post elaborates:
Thomas Mann plays Toby, an outsider at a boarding school who goes from small-time dealer to preppy Pablo Escobar, importing large quantities of cocaine from South America to satisfy the appetites of the privileged, party-hearty student body. While the character doesn’t go by Oatis’ name, Toby is heavily inspired by him, and Oatis sold the production company his life rights.
“It was strange watching the movie. It was tough,” Oatis, now 49 and a lawyer in Connecticut, tells The Post. “I winced at the depiction of my mom [as materialistic]. She takes this much harder than I do.”