'Preppie Connection' Director on Transforming '80s Boarding School Cocaine Scandal into Movie

Courtesy of IFC Films Release
'The Preppie Connection'

Joseph Castelo explains what's at stake at a crucial moment toward the end of the film, in which star Thomas Mann ('Me and Earl and the Dying Girl') is unable to turn his back on what he's done, making the same decision as his real-life counterpart.

In 1984, Choate Rosemary Hall student Derek Oatis was arrested for trying to smuggle $300,000 worth of cocaine into the U.S. The scandal was the subject of a 60 Minutes piece, and the story spread throughout the boarding-school community, where it caught the attention of Joseph Castelo. His lingering interest in the story, particularly what happened to Oatis and the other players, ultimately led him to make a movie based on the incident.

"I always wondered what happened to [Oatis] and what happened to the other people in the scandal. The story was just buried. I think it had to do with the powerful people that were involved, and the story just went away," Castelo tells The Hollywood Reporter. "I went back and I dug it up and I met with Derek and I talked with him about the story, and it was just a compelling story about identity for me, something that I really connected to from my own experiences. And I love the period; I love the backdrop; I love the alternative preppie culture in the '80s."

The Preppie Connection, which is now in select theaters and available on demand and on iTunes and Amazon, stars Thomas Mann (Me and Earl and the Dying Girl) as the Oatis-inspired Toby, a working-class scholarship student at the tony Sage Hall boarding school, who uses his access to cocaine as a way to fit in with his more privileged classmates, including the elusive Southern girl he has a crush on, Alex (11.22.63's Lucy Fry). While a number of names and locations are changed, Castelo, who directed the film and co-wrote the script with Ashley Rudden, says he "stayed along the footpath of what actually happened."

"So many things about the film are a truthful retelling and authentic about what actually happened," Castelo says. "[Oatis] was a scholarship student who was completely out of his element in this very rich and powerful boarding school. He was struggling with issues around his identity. He very much wanted to connect with this girl … and he saw that the quickest way from point A to point B for him was to get them cocaine … For me, the cocaine became a metaphor for his identity struggle and once he achieved that identity, what lengths would Derek go to to hold onto that."

Castelo also changed some of the smaller moments, like Toby's awkward moment in the chapel on his first day of school. In the "even more embarrassing" reality, Castelo explains, a radio antenna fell on Oatis' car at a football game. He also drew on elements of his own boarding-school experience in the '80s, including dorm life, the music, the clothes and the look and feel of the campus, as well as more local versions of illicit behavior.

"To me when I look at this film, that's how I remember boarding school in the '80s because I was there," Castelo says. "We had some drug-dealing incidents at our school, so I was accustomed to how this stuff happened, how it went down, the language between students, how they moved through the school and kept everything secret. There was no social media, smartphones, wifi; kids could fly under the radar and get away with so much more than they can today."

Toby's pursuit of Alex, Castelo adds, is representative of a larger quest.

"I think that getting Alex in the film is validation for his character. He wants to be accepted," Castelo says. "At a certain point he wonders whether his relationship with her is actually real, if she really does care about him. He never really knows and he never really puts his trust in her or in this group of people. He doesn't trust the situation and in a way he doesn't trust himself. He's at that age where younger people are searching for their identity. I think it's all sort of wrapped up into one thing with Alex … I think that his relationship with Alex is symbolic of the acceptance that he wants from the entire social circle."

The key moment towards the end of the film in which Toby has a choice to make involving Alex and the cocaine he's acquired also really happened, with Oatis making a similar decision.

"To me that felt like a true tragedy. The archetypal tragic hero has that moment where he or she can choose a different path and he didn't. And that's really what compelled me to his character," Castelo says.

"I don't think he trusted himself and knew himself well enough to [make a different decision]. He didn't know — at that age, you're coming into an understanding of what real love is — I don't think he really understood that. I don't think he let Alex in enough to trust her," Castelo explains of why Toby makes the decision he does. "What we were working with in that scene dramatically was Thomas Mann was working with the choice, if I [do] this, I give up everything and I give up Alex, so he really had to wrestle with his own character's confidence and struggle with identity, all wrapped up in [a] bundle of cocaine."