Growing Up Gloucester

By Rachel Baker | Boston Magazine |

Stuff was different before. It used to be that on summer Fridays, Kaila Simpson would push the limits of the "No Loitering" sign in the McDonald’s parking lot near Gloucester High. Or she’d catch a ride, head down Main Street and past the pier to the Dunkin’ Donuts at the Stop & Shop where her cousin works and where Kaila can score discounted Milky Way hot chocolates, the most delicious drink in the whole world. Kaila lives for summer. She sunbathes with friends at Good Harbor Beach and watches the sunset from the old cannons at Stage Fort Park. At night she and her friends will sometimes go hang out in Rockport at Steel Derrick Quarry, which is deep enough into the woods that the cops can’t break up whatever boozing or fighting is going on.

But today was no ordinary summer day. Kaila, who had just turned 17, was set up at her round, oak-looking kitchen table. And she was even more distracted than usual by her pink Razr phone. Each time it bumped to the tune of Usher’s "His Mistakes," Kaila would slide off her chair and scamper across the living room in search of clearer reception, leaving a trail of Paris Hilton perfume in her wake. At the window, Kaila raised her normal voice a full octave to offer a drawn-out "Hellooooo," filtering the happy sound through a wide grin.

This time, it was NBC on the line. They wanted Kaila, along with as many of her pregnant and teenage-mom friends as she could help them find, to appear on the Today show. Chin down, head glued by the phone to her right shoulder, grin still intact, Kaila stroked her messy blond side ponytail as the producer hit her with the full pitch: They’d fly her down to New York, put her up in a fancy hotel, do her hair and makeup. And, on national television, Kaila would wow millions of people with her story. Sounded like a sweet deal. But Kaila had something else in the works. Letting the producer down gently, she told her no thanks.

The better offer Kaila was sitting on was from The Tyra Banks Show. Kaila, you see, feels a bond with the diva supermodel host. She knows they both can be goofy and tough and sexy and real, and therefore had promised the Tyra show her exclusive.

The calls rang in all afternoon. Some from other TV producers and newspaper reporters, others from relatives and friends of the family who’d seen Kaila in that morning’s Herald. That little article would be only the beginning of her stardom, she assured those who called, in a voice that wavered with the kind of excitement normally reserved for discussing the Jonas Brothers, whose pictures she’s taped up in her bedroom. That night she would be on Channel 7. And soon, of course: "I’m going to be on Tyra!"

The Herald had gotten its story when reporters spotted Kaila and a couple of her friends with babies in tow strolling a stretch of waterfront sidewalk known as the Boulevard. It was from these reporters that they first heard there was some sort of pregnancy pact among the girls of Gloucester High—which they, being girls of Gloucester High, found totally bizarre. Things got more intense when they got closer to McDonald’s, where a Channel 7 news team had camped out. "Like they were sitting there waiting for people with carriages to walk by," Kaila remembers. "They just whipped out their cameras and started rolling."
And that’s when Kaila did what she usually does, and took charge. In the clip that ran on Channel 7, she struts across the screen pushing a stroller. She is asked what parents can do to solve this pregnancy "epidemic." Her hand clenching a cigarette and swatting the sun out of her eyes, she replies, "Get into their kids’ lives. Half the parents around here have no clue what’s going on with their kids."

All the attention was somewhat intoxicating. Also strange—though this strangeness only made it more alluring—since, as Channel 7 had failed to mention, Kaila herself was not a teen mother or mother-to-be: The baby she’d been pushing was her one-year-old niece. Her real role in the whole drama was as her pregnant friends’ spokeswoman. She had always been the popular girl within her crowd, the kind of kid who sets the nightly social agenda and orchestrates the matchmaking between her friends and the older boys. Why shouldn’t she also be a quasi-agent when the press came calling? Her friends had enough to deal with. This was how she could help. Plus, the way she saw it, she could share the limelight without actually being saddled with a kid of her own. "I know how they are and how they think and everything," Kaila says. "I basically say what they’re feeling about things because I know them so well."
So yeah, stuff was different. But it was going to be cool.

  • C

    As a graduate of Gloucester Public Schools and a former resident, this article presents a schewed and biased representation of life in the city. It seems to imply that everyone who went to high school there doesn't expect to go anywhere and there aren't any opportunities. Sure, in any town you will have kids in high school who end up dropping out and not finishing school, or getting pregnant in high school; but to characterize that as the majority of the school body is unfounded and a gross generalization. I graduated from Gloucester HS in 2001, and the majority of my class went on to college for their undergrad degrees and now lead successful careers. I also know many people who are now in graduate or law school, including myself. As such, I am appalled at the total lack of analysis that has gone into this article, relying on a small pool of individuals to mischaracterize an entire community. How about broadening your pool of interviewees and getting the "real" story – how many

  • courtney

    I am a graduate of gloucester high school and this article is a complete misrepresentation of this town. So many of my friends who graduated from GHS have go on and gone to very good colleges, grad schools and have become doctors and lawyers, teachers and other great professions. This article makes this town sound like a dump hole where people do not go any where in life and where all our dad's are fisherman. I went on to graduate from a great college in Washington DC with a father who works in boston as one of this countries best environmental advisors. Gloucester is a beautiful town with some of the best beaches in New England….an amazing movie was filmed here with an amazing story…a great high school where students have gotten a great education that has teachers who I as well as many others will never forget. So lets get the real story straight about this town…Count how many have become successful in their life from GHS…do you know the number?