Latin’s Crossing Guard

Illustration by Raymond Biesinger

HUBERT TAN was not alone. On four different days last fall, the high school senior stepped out the door of his Malden home and made his way to Boston Latin, one of the country’s best public schools. But Tan never saw Stephen Hickey, an investigator for Boston Public Schools. BPS records show that Hickey arrived each of the four mornings at 6 a.m. and parked discreetly on Tan’s street. According to Tan, he snapped surveillance pictures. When Tan got a ride, Hickey ran the car’s plate and found it was registered to a Malden address. “It was supposed to be some sort of covert operation,” Tan says today. “I had absolutely no clue.”

Although Tan didn’t know it, he was one of about 100 students Hickey investigated for residency fraud last year. Only Boston residents are allowed to attend the city’s three exam schools, and Hickey now had proof that Tan actually lived in Malden. So he got the boot, as did 17 other Boston exam school students in 2009.

To be fair, Tan’s case was unfortunate: His parents’ divorce had forced him to move out of the city before his sixth year at Boston Latin. But the school, which runs from grades 7 to 12, is so highly ranked that certain suburban parents will do almost anything to sneak their kids in. Some have even leased apartments just to establish city addresses. (Of course, it doesn’t hurt that rent is often cheaper than private school tuition.) Hickey’s job is to make sure no one trying to cheat the system gets away with it.

This year, the city is giving him a little help. Parents once had until February to prove – or fake – their Boston bona fides, but now the deadline has been pushed up to November 5. The extra three months will give Hickey the time he needs to set up his stings. As for what those consist of, well, that’s top secret. “We try to limit when he speaks to reporters,” says a BPS spokesperson. “We don’t want to tip his hand.”