We went to Tom's at six in the morning and after detention each Sunday. We went even when the roads hadn't been plowed and when the wind chapped our faces. We went to study, to listen and to smoke. We went for his one-dollar corn muffins and flavorless coffee. We went to hibernate from the cable-knit phonies and the sea of pastel. We went whenever someone was kicked out, but even with my penchant for rule breaking, I never had to worry about that. What elitist boarding school would expel a ninth-generation legacy in the midst of a capital campaign? Maybe they held onto me those four years in a selfish attempt to weasel even more dough from my grandparents, who had, unbeknownst to me, been annually emptying my trust fund with their "philanthropic" donations to Eliot Academy. Whatever. It's not like I even wanted it, anyway. Money just fucks things up. But instead of helping AIDS victims or homeless children, my grandparents chose to squander it on new dorms for over-privileged yuppies.
I don't mean to sound so bitter. It's not like I haven't been pampered myself. On the contrary, I've led a grotesquely affluent life, too similar to my classmates' than I'd like to admit. My parents parade in the company of New York's "oldest and finest," and my mother's milieu is limited to those with Ivy League educations and lineages akin to that of Westminster Dog Show winners. In a pathetic rebellion to my overbearing mother, my father refuses to give up smoking cigars, igniting many a scotch-induced bicker in the library. Neither cares enough to notice me, and I wasn't surprised when they slipped Eliot's application under my door the morning of my thirteenth birthday.
There wasn't any point in arguing. It had been settled long before I had even been conceived - what Victor-Smith spent the "best four years" of his life anywhere other than the quaint (read: euphemism) town of Wallingford - "Wally World" - Connecticut? It was unheard of. In a sly attempt to irk my father, I would whisper the name of Eliot's rival school during mealtimes; "Hartfield" became as forbidden a word as "fuck" in our townhouse, and my father forced me to return the several sweatshirts I had ordered online with my mother's credit card. I had, at the ripe old age of fourteen, mastered the art of mischief, and it breathed life into an otherwise dull existence.
On my last morning in New York, my father lingered in the doorway of my bedroom. "You," he said as I packed my small trunk (I was convinced I'd be returning home after a few weeks), "must not be the first to stain the family legacy, Nick." With those warm fuzzy words of paternal support, he informed me that our driver, Lars, would soon be arriving to take me to Eliot - that he and my mother had pressing social obligations, but would be there for Parents' Weekend. I knew my father thought he had my best interests in mind, calling the town car to pluck me from the city and dispense with me in rural Connecticut, but it blew my mind that he couldn't comprehend the social implications of such an arrival. Not only would I be the one student without parents in tow, but I would be forever branded a pretentious asshole. Cool. Thanks, Dad.
After bidding the Victor-Smiths goodbye, I ditched Lars and hailed a cab to Penn Station where I boarded the 12:15 Amtrak to New Haven. From there I would switch lines to Wally World and begin my adventures at Eliot Academy.
It didn't take me long to realize my preconceptions about boarding school were horribly correct. There were the field hockey girls in pleated skirts from New Canaan and the "sweetlaxers" from Maryland who "rocked" Rainbow flip-flops all year round. But of all the boarding school prototypes, the worst were the hockey players. With their "sick flow" hanging in semi-mullets under their winter hockey hats, these upstanding young gentlemen made more catcalls at me than at the puck sluts. They'd never before encountered a gaunt, self-proclaimed intellectual who kept a dog-eared copy of One Flew Over the Cuckoo's Nest tucked into his back pocket. Anyone who wore a tattered leather jacket and left a trail of cigarette smoke in his wake was foreign to the prep school crown, too. I mean, they'd obviously met kids like me before, but I guess I was more visible than the other beatniks (and pseudo-beatniks) at Eliot. Must have been my stunning good looks that caught their attention.
Much to the Victor-Smiths disappointment come Parents' Weekend, I had not conformed to the "Varsity Life" mentality of the douche bag hockey boys, finding instead confirmation in a tribe of eccentric characters who'd never heard of Fairfield Country or even Jupiter Island, for that matter. We had two things in common. We hated Eliot, and we ripped cigs at Tom's. We hiked seventeen minutes (five on bike) to Tom's at 6:03 several mornings a week to avoid the Dean's omnipresence. He had cultivated the rate skill of recruiting all five (some would argue six) senses to detect any rule breaking on campus. Don't get me wrong - of course the faculty knew about Tom's (his dodgy history of mafia infamy was legendary in Wally World) - but with the exception of a few vengeful science teachers who would sometimes pop in at 6:30 to nab smokers, most faculty members feigned ignorance of our breakfast spot. If they were to shut Tom's down, we'd migrate elsewhere to silence the screeching nicotine monkeys on our backs, and we'd also make a big fucking stink about it. Tom's, you see, was our haven.
My prefect took it upon himself to take my Tom's virginity, if you will. He differed from the majority of boys on campus; he wore a multi-colored Mexican poncho and Birkenstocks, smoked American Spirits and went the entire month of September without washing his hair. It was just how he lived his life. When he insisted I join him and his buddies for breakfast one morning, I agreed to meet in front of the library steps at 6:03 am (dormitories were unlocked at six, and it took us about three minutes to walk to the library), where the group of raccoon-eyed kids always convened. When "lights-out" rolled around the night before, I realized that it was the first time a strict 10:45 bedtime hadn't really pissed me off. I lay in bed, waiting to hear the 11:00 pm train pass through Wally World on its retreat to the city. The next day I'd lose some of that third-form innocence - I was going to Tom's.
It was snowing that morning, and icicles congealed on my sopping wet hair as we hurried downtown, descending a long hill until we reached the train tracks where I had disembarked only a few months before. Tom's Coffee Shoppe was the only business on Main Street with buttery light oozing from its front windows. Nervous, I let the seniors, each clad in a gray sweatshirt with their names emblazoned in red on the left and Tom's Coffee Shoppe etched on the right breast, enter the den first. One of the boys wore a trucker hat with the same lettering and train logo.
I noticed the stench first. Everyone does. A dense perfume of grease and cigarette smoke hovered in the air, staining the ceiling with splotches of mahogany. "You'll get used to it, Nick. You might even prefer it over that shit your mom sent you... what was it? Aqua Di Gio?" Dave laughed. My cheeks still stinging, I glanced at the narrow room. The Eliot kids sat in cramped booths on the right, hollering at each other as they fixed themselves coffee from behind the adjacent counter. Sitting on stools with their backs facing the booths were the tattooed construction workers, their ashtrays brimming with crushed Marb Red's. They wore paint-splattered construction boots with denim suits, grunting quietly - if at all - amongst themselves. They had grime lodged beneath yellowed fingernails, as if the grease had saturated every facet of their being. These mangy men with crevices engraved across their faces were as emblematic of Tom's as his griddle. It seemed they had sat on those same cracked leather stools every morning of their working lives.
The walls were jacketed with three decades worth of signed photographs of Eliot students smiling with Tom. He's worn the same tennis shoes, white shorts and white T-shirt since the Shoppe opened in 1910, as the "est. 1910" on the oil-speckled menu above the counter joked. Nothing cost more than five bucks, but, as I learned that one morning, it "didn't really matter if you didn't have the exact amount." You paid when you could, tossing the bills in a pile on the counter. Dave then instructed me to scribble my order on a napkin, and we walked it back to the kitchen where Tom worked, frying the artery-clogging delicacies that became staples in my diet. We watched him as he fried; he was even older than the construction workers, speaking in terse sentences that were difficult to understand. His movements and posture reminded me of a prehistoric dinosaur, and we idolized him because he was a creature of the past - the antithesis of Eliot, a townie toiling away in the grimy working class work we so admired.
When Dave and his rat pack graduated, I decided it was time to make a few friends my own age, and so I formed a clan of younger Tom-devotees. There was Lydia, a burgeoning cokehead, Katherine Koh from Singapore and my two closest friends: Wiley and Wole Wilkinson. The twins were new sophomores from London and channeled every ounce of their creative energies into evading Eliot's disciplinary policies. Wiley spurred both Wole and me into the majority of our less-than-legal exploits. He calculated Community Safety's nighttime route around campus and vigilantly made note of the teachers who walked their dogs in the early hours of the morning. The October of our fifth-form year Wiley somehow obtained a master key (a feat rarely accomplished at Eliot), allowing for all sorts of after-curfew excursions. The three of us were regulars on Dean's Row. They always caught us breaking minor rules, and I have a feeling Dean Warden derived sick personal satisfaction as he sentenced us to weeks on end of Sunday detention. I guess it was his way of telling us we were on the "red flag" list, but with that raw teenage arrogance boiling with the fury of a caged animal, we thought we were invincible. After everything that we'd gotten away with, though - anyone would have thought the same.
