Once upon a time, 33 years ago on this date, the first Head of School Day was announced. Students and teachers alike did not know what to make of the now-famed day, most likely because it was not something they were warned about. Here is the story:
Long ago in the White House on Main Street, the Headmaster of Phillips Academy sat in his fox hollow chair. He was upset, for he had missed his last three parlays by just one leg. Having enough of this misfortune, the Head of School decided to do something to brighten his mood, he decided to start a tradition to distract him from his sadness: Casino Night!!! (obviously)
Students were not allowed at this event, for obvious reasons. In fact, there was no event — the Head of School simply took an unannounced vacation to Las Vegas, along with 7.6% of the school’s endowment. That night was NOT detailed in Phillips Academy records, which is why you have never heard of it — but legend has it the ‘Beer Mile’ used to be a record displayed in Borden, dated to that very night.
The only reason we know about this day is that 18 Lowers were also (illegally) in Las Vegas, and although they did not wake up with a Tiger, a Baby, and a Dead body, they did witness the head of their high school stumble into a Vegas Motel at 2 AM on a Monday Morning with an Exeter Tattoo on his chest. They hatched a plan, seeing an opportunity to save themselves. They hacked into his computer, ignoring the strange calendar, and sent out a school-wide announcement. Head of School Day was born.
And so the students returned to Campus the following day — 200 Million Dollars richer (the headmaster actually won Roulette), and they went down in history as the first 18 Phillips Academy Graduates to be arrested for Gambling Fraud.
