Real-Life Prep School Scandals So Crazy They Sound Like Fiction


Today marks the release of Jennifer Miller’s stellar debut novel The Year of the Gadfly , a tale of prep school scandal and secret societies starring a very precocious young lady named Iris Dupont, whose best and only friend is the chain-smoking ghost of famed broadcast journalist Edward R. Murrow. If it sounds weirdly wonderful, it is — Iris would kill us for using a cliché here, but we can’t help but call the novel compulsively readable, and it feels a little something like a cross between The Secret History and Gossip Girl, although with significantly more masturbation scenes than the former and more dusty tomes than the latter.

To celebrate her book’s release, Miller, an accomplished journalist herself (her non-fiction book Inheriting the Holy Land: An American’s Search for Hope in the Middle East came out in 2005), has obliged us by putting together a list of some of the craziest real-life prep school scandals in recent memory, so weird they almost seem like fiction themselves. Click through to read up on cheating teenagers, bad touching, and Big Brother-like surveillance, and then be sure to pick up a copy of The Year of the Gadfly for even more (fictional) prep school juiciness.

Are Your Panties in a Wad?

I’m not sure if the real scandal here is the fact that five cheerleaders at McKinney North High School called “The Fab Five” took pictures of themselves holding penis-shaped candles in the “Condoms To Go” store outside Dallas or the fact that their school district spent a whopping $40,000 investigating the incident. In defense of the school district, the lawyer said the photos were “creepy.” Apparently, the ringleader of The Fab Five is the principal’s daughter, hence her immunity for all kinds of bad behavior, like talking on her phone in the middle of class, telling a teacher to “shut up” on one occasion and, on another, demanding that the teacher “pull [her] panties out of a wad.” This makes me wonder if the teen in question knew that this was the 21st century (2007, to be precise). Or maybe the fact that this happened in Dallas attests to the fact that these girls talk like they’re still on a Laura Ingalls Wilder homestead.

The Great Coke Bust of 1984

In high school, every day at lunch, a friend of mine would take orders, collect cash, and do a burrito run. He’d figured out that a “Buy Six, Get One Free” deal at a nearby Mexican café would not only get him free lunch but earn him a profit. At the Choate Rosemary Hall Boarding School in Wallingford, CT, Matthew Robert Holmes took the burrito scheme to extreme and illegal lengths: collecting money around his dorm, hopping a plane to Venezuela during spring break, and attempting to smuggle 340 grams of cocaine into the US. Unfortunately, Holmes did not plan on US customs. In the courthouse, after pleading guilty to the charges of possessing, importing, and distributing cocaine, Holmes said, “I did not realize the seriousness, the full extent of my participation.” In the end, Holmes was lucky. He faced a $25K fine and up to 15 years in prison but got off with a five-year suspended jail sentence, five years of probation, and 5,000 hours of community service. One thing’s for sure: the kid would have been better off dealing burritos.

Restless Virgins

Here’s one way to make the New York Times Extended Best Seller list: mine your own high school for scandal. In 2007, Abigail Jones and Marissa Miley, alumnae of the Boston-area Milton Academy, published Restless Virgins, a non-fiction account of a 15-year-old girl who was caught giving oral sex to five varsity hockey players in the school locker room. The authors call the book “a compassionate, honest narrative” and not softcore porn as some critics have claimed. They say the book opens up an important discussion about teen sexual behavior but that the title “Restless Virgins” doesn’t just apply to sex. “We think that every teenager is virginal,” one of the authors told Time Magazine. “They’re virgins in life; they’re having all new experiences. And they’re restless for all of these experiences.” Maybe. But Restless Virgins sounds like a bad soap opera or a grocery store romance: all heaving bodices and Fabio hair.

The Russian Death Squad for Girls

In 2009, a student sued Miss Porter’s School in Farmington, CT, claiming that she’d been harassed by a vicious secret society. As Vanity Fair notes, Miss Porter’s alumnae include heiresses to “one brand of breakfast cereal (Kellogg’s), three meats (the Raths of Iowa and the Swifts and Armours of Chicago), and the world’s most famous dough (Pillsbury).” School loyalty is of utmost importance at Miss Porter’s, and has been upheld over the years by a secret society called the “Oprichniki.” The group is named for a 16th century Russian secret police force, formed by Tsar Ivan the Terrible to quash his enemies. The Russian iteration rode black horses to terrify dissidents and were ordered to execute anyone who opposed the regime. At Miss Porter’s, the Oprichniki includes many daughters of alumnae and is responsible for initiating and hazing new students. Some scholars trace the origins of the Oprichniki not to Ivan but to his second wife — which only proves that having women in charge of the world’s governments would not necessarily lead to a more peace-loving global environment.

The Mommy Tantrum

Who said school scandal is just for students? Last spring, a Manhattan mother sued the York Avenue Preschool, claiming the school failed to prepare her tiny tot for Ivy League admissions. She paid $19K of tuition, believing the school’s promises to teach one alphabet letter per week. Instead, her four-year-old daughter was stuck learning about shapes and colors. And this, the mother said, failed to prepare her daughter for prep school entrance exams, which in turn, ruined her chances of getting into the Ivy League college of her choice. Let this be a formal invitation to the mother in question. For $19K, I will gladly teach your daughter the alphabet and throw in shapes and colors at no extra charge.

Big Brother Gets an F

I definitely don’t want to see what a 15-year-old boy is doing in the privacy of his bedroom, so why in the world would his principal? In 2010, Blake Robbins, a sophomore at Harriton High School in Pennsylvania, was called into his principal’s office and accused of inappropriate behavior, including pill popping. The evidence? School administrators had activated spy software on Blake’s school-issued laptop and were watching him at home as well as capturing images of his video and gchat discussions with friends. His parents filed a class-action lawsuit against the Lower Marion School District, citing violations of the Fourth Amendment, The Computer Fraud Abuse Act, and the Electronic Communications Privacy Act, among others. Turns out, the school had been illegally watching students for months and even lied to students, saying webcams that turned on periodically did so because of a mechanical “glitch.” The lawsuit was settled out of court for $610K in favor of the plaintiffs. Do Lower Marion schools teach 1984? Maybe it should be required reading for all incoming teachers.

The Cheaters 101

Look! Over there! Mussolini is playing laser tag with General Franco! In 2008, students at the prestigious Harvard-Westlake school in Los Angeles conspired to steal European history and Spanish exams by distracting their teachers. Teachers became suspicious when a number of students (ostensibly the academic runts of the litter) performed exceptionally well on their tests. Six sophomores were expelled for taking part in the test heist and a dozen more students were suspended.

The Cheaters 102

The bubble (test) has burst! In 2011, 179 teachers in Atlanta schools were accused of cheating on state standardized tests — erasing their students’ wrong answers and changing them to the correct ones. Thirteen principals named in the investigation were forced out and 41 more teachers ran for the hills before the state’s report was released. The school district says it could take years to adjudicate the cases of the remaining 137 educators. In the meantime, they won’t be allowed back into classrooms. Does Atlanta have an equivalent of New York’s Rubber Room? These teachers should be forced to take the ERBs indefinitely.

Double Cheating (103 & 104)

For God sakes kids, just do your own work! In 2003, ten students at the Landon School in Bethesda Maryland cheated on the SATs. They passed around answers in their unsupervised section of the testing room and shared a smuggled-in electronic dictionary and calculator. Administrators dismissed rumors of cheating until the scores came in — some of which had skyrocketed by 200 points. (The average increase is 50). Eight of the boys were suspended and two expelled. Three years prior, at the same school, 15 students were implicated in cheating on an honors pre-calculus exam. Two were expelled and the rest suspended for a week. So many of the students implicated were lacrosse players that practice was cancelled. The coach was so pissed that he called the kid who snitched on the players a narc. Yeah, real mature.

Hot Off the Presses!

No list of school scandals would be complete without at least one act of sexual deviance. In 2002, the Massachusetts Council Again Discrimination found “credible evidence” that the former headmaster of the Berkshire School sexually harassed 20 women at the school, including students. On one occasion, he kissed the wife of a dean “full on the mouth” at a faculty party. The secondary scandal, however, was the school’s alleged attempts to suppress the incident. When the Boston Globe Magazine ran a cover story, School for Scandal, an unidentified man in a baseball cap drove around the region buying up all the papers. The school claimed it was not behind the run on papers. “Those are Stalinist Russia tactics,” a school spokesperson said. However, librarians at the Sheffield School were instructed to remove copies of the Berkshire Eagle that also covered the scandal. Shady? Yup.