“And what exactly would be involved as a director of student athletics?” Doucheborn asked.
“Student director of athletics,” I corrected. “Ensuring that the health and safety requirements of my fellow students are upheld and that they are adequately hydrated at all times.”
“Right . . . so . . . a water boy?”
“It might be considered that at lesser establishments, but I really would prefer the title of student director of athletics.”
Both sighed. I could see Doucheborn attempting the calculations in his head. He wanted me out of his face as efficiently as possible. Then he took the bait.
“Fine. Whatever. Get out of here.”
I thanked them both formally, closed my case, and exited.
And so I was appointed as Brewster Academy’s first SDA (student director of athletics). Which was good, as I had five hundred business cards signaling this fact. Even for me, it was a pretty ballsy coup. As well as now being excused from all forms of physical activity, I knew that the job came with a very special perk. Doucheborn and Subaru Sue had made an error that would come to haunt them and cement my reputation as the biggest asshole that the school had ever encountered.
Boarding school proved to be the ideal environment for me. It provided the blueprint for everything I would go on to do in the future. With a perfectly defined structure of rules and conventions that I was able to subvert and manipulate, I quickly adapted, developing a particular range of skills. It’s why I was excited to go there in the first place. Having run out of things to fight against at home, I needed more problems and regimes to wriggle out of. I needed to increase the gradient on the treadmill.
As far as I’m aware, I was a boringly satisfied kid. Rich, spoiled, Jewish. The classic combination. That all came screeching to a halt around my tenth birthday—incredibly, the exact moment of the change was documented. There’s a picture of me sitting in the cockpit of a Boeing 727, wearing the pilot’s hat and looking like the happiest fucking kid in the world. We were off on a family vacation, and, back before you’d be arrested for saying “box cutter” on a plane, I was invited into the cockpit, where this picture was taken.
It’s an expression of relief I’m wearing in the image. Up to that point I had no idea what I wanted to do or to be. And in the community I grew up in, your role in life was designated pretty early on.
“You’ll be a lawyer. You’ll be a doctor. You’ll be in business, just like Daddy.”
All was prescribed and decided. And I felt that same pressure to conform, even though something inside me fought against it. So when I sat in the cockpit, all felt right. That’s exactly what I wanted to do. I wanted to be a pilot. It made perfect sense. The glamour of it, the control. This was back when flying still had some mystery and cachet surrounding it, before planes became flying 7-Elevens. Plus I was spending every waking hour locked in my room, playing on a flight simulator. (This was prepuberty, obviously). It was cool to be a pilot; it impressed people. Except my parents.
When I told them of my intentions, they laughed in my face.
“A pilot? You can’t be a pilot. We don’t know any pilots. There aren’t any Jewish pilots.”
Who does that to a kid? Just humor me, for fuck’s sake. But that was the problem. My loving parents don’t have my sense of humor. It felt horrible, a massive disappointment. I felt ashamed, like someone had just wandered in and caught me jerking off. It was the same sensation.
I was never the same after that. My relationship with my parents degenerated. They’d changed me, they saw my vulnerability, and they could never empathize with me. I realized they were wrong, and that’s pretty devastating for a kid. Even if I couldn’t verbalize it, I knew that whatever I would be, it would be the exact opposite of what they wanted. If I couldn’t be a pilot, then I’d be the best passenger the aeronautical industry had ever encountered. The rest of my life would be an extended revenge against their hopes and beliefs.
There were flashes of this before I reached Brewster Academy. I can remember being in sixth grade, soon after the cockpit incident. The rest of my class was engrossed in math problems. At that early age, I’d already learned to sit next to the Asian girls, as they knew all the answers. After I’d wasted pretty much the whole class writing punch lines, I realized I needed to attempt some work. I was leaning across and squinting so hard to see the answers of the Korean chick next to me, it looked as if I were making fun of her in a Hello Kitty sort of way. And I found this unbelievably funny. I just started laughing, and I couldn’t stop. First, because I mistakenly looked like an enormous racist, and second, because I was the only person in the class, barring the teacher (and that wasn’t a given), who would get the joke. They were fully immersed in their pointless activity while I was having fun. Joke’s on Jew.
Coming hard on the heels of my pilot phase, it was a further revelation. Their conformity amused me. Why the fuck were they sweating over equations when they could be yukking it up? It made no sense to me.
The following summer I was sent away to camp. It wasn’t officially a Jew-kid camp, but it certainly had those leanings. It was the “right” camp, the one considered correct to attend, which was a complete affront to me. Why the fuck would I want to go where everyone else was going? I had to deal with those dicks during the rest of the year; why would I want to sit around a campfire with them?
I had no interest in going, and once I was there, all I wanted to do was swiftly get kicked out and never invited back. The cool kids at the camp all played tennis; they represented the “alpha males.” In an unspoken fashion, this was how the hierarchy was established, by the accuracy of your first serve. I couldn’t play tennis. I hated tennis. To make my feelings clear, I decided to piss on the tennis court. Everyone saw me—it was during a match. It was probably the most subversive, blasphemous thing I could have done.
Campers and counselors alike were mortified. It was like I’d rectally probed someone with the camp’s ornamental replica tomahawk. It wasn’t subtle, but it helped do the job and taught me a valuable lesson. Yes, I could have spent hours trying to come up with the perfect, complicated scheme to bring about my release, but sometimes all you need to do is piss on the tennis court.
Incredibly, this wasn’t a serious enough crime to immediately result in expulsion. It was more of a crime against their inherent beliefs than a chargeable offense. So they pinned a series of trash-can fires on me for good measure. I didn’t set any fires—I wasn’t a pyro. There were a lot of weird kids at that camp.
This mild level of delinquency and unhappiness continued until my parents were sick to death of me. They just wanted me out of the house and didn’t really care how much it cost them. It cost them roughly $35,000 a year. Attendance at Brewster Academy was considered a privilege. It had to be at that price. But my parents and I knew I was being shipped off for the sake of their sanity and their standing in our hometown. I had started to attract attention, the bad sort of attention that I enjoyed. It was the very thing they fervently strived to avoid. All I had to do was not get thrown out of the joint. I managed to achieve this. Just.
When I got there, it was quite a shock. The guidebook was as thick as the yellow pages, with rules covering everything from eating to grooming. Every aspect of your life was regimented and scheduled. You ate, slept, and were educated at distinct times and couldn’t beat off without a signed note from the nurse. I’d never been in an atmosphere as tightly controlled as this. The campus was beautiful, the kids were cruel, and the law was strictly enforced. Anything could be considered an altercation, and punishment was swift, vengeful, and often unfair. This was going to be a challenge. And behind it all was Doucheborn.
Doucheborn was the principal architect of the establishment’s regimen, and he epitomized everything I’d grow to hate in the world and would become determined to eradicate. As I explained, he was “dean of students,” but really he was the warden, and we were his inmates. He lived and died by the book. Which is why I
took every page of the book, ripped it out, and wiped my ass with it—figuratively. Now I brand any example of small-minded wretchedness and people who possess his particular brand of charmlessness as “Doucheborn.”
My first year there was entirely an operation in casing. I watched; I observed. I worked out how things ticked, where the weaknesses lay, who to target for maximum efficiency. I pored over the handbook as if it were a map leading to maximum disruption. I didn’t socialize; I wasn’t interested in forming friendships or forging bonds. I looked upon the whole experience as an exercise in how far I could push things before they fell over. It was the only way to stifle the boredom and disrupt the status quo. By the start of the next year I was ready to act. I started with my wardrobe. I transformed.
My nickname on campus soon became GQ. It wasn’t necessarily a term of endearment. I wanted to look like something you’d see spread across that month’s Esquire. I always abided by the specifications of the dress code but never indulged the spirit of it. You were required to wear a blazer, a shirt, a tie, khaki pants, sensible shoes. I wore all those things. They just happened to be the finest designer examples of them, purloined during holiday romps through Neiman Marcus.
Ferragamo, Zegna, Prada, Burberry—I dressed decades older than I was and always accessorized with Louis Vuitton. It wasn’t preppie in the least, way more Madison Avenue with sleek, debonair lines. I wore Gucci shoes, even in the depths of winter when the snow was up to your ass. But I made my mark. I was noticed. The kids made fun of me. Good. I loved that attention, the negative attention. The authorities at the school hated my new look. They knew I was up to something; they just couldn’t quite work out what it was. This was to be the model for my behavior during the next few years.
I now began to identify particular rules and devise ways to disable them. Why? Because that’s what I excelled at. I was never going to make it onto the mathletics team or be the lacrosse captain. If that was your lot in life, good for you. But those people are completely designated into those roles. Every math wiz looks the same; every high school sports star acts the same. They really want to be recognized and lauded for that shit? But that was exactly what was expected of you. Do well in these rigidly narrow areas, and we’ll give you a cheap trophy and a pat on the head. Excuse me if I don’t perform backflips.
I had other ways to be recognized. My skills lay in self-promotion. It was like I was campaigning for a platform—and that platform was me. And like all politicians, I wanted people to notice me, to be entertained. It all became about performance, what could I do to provide maximum impact with minimal effort. I learned a massive amount in that first year. Not in class, of course, but about my particular talents and how to utilize them. I was born to subvert and manipulate. For the first time in my life, I was emerging as a role model. While many still despised me, a growing element started to notice and appreciate my efforts. I was totally unique, and if you’re unique, you’ll eventually get noticed. I was becoming a star. I honed my act over the coming months.
My Jewlosophy has always been to target the one thing you excel at and be the Tiger Woods, Lance Armstrong, and Mike Tyson of your field. OK, those are great bad examples, but I want to be on the highest part of the podium. You need to be the best of breed, the proprietary eponym. In my view, if Justin Ross Lee doesn’t come up as the number one answer on Family Feud when the has-been host asks, “Who is the biggest asshole self-promoter in the world?” I have failed. So, at Brewster, I focused on what I was good at, which was bucking the system. The clothes and the fashion were just the hors d’oeuvres.
From Water Boy to Cable Guy
So the huge, glaring error that Doucheborn and Subaru Sue made, entirely instigated by me, was a by-product of my new water-boy status. They assumed I just adopted the lowly position to get out of doing gym, which was completely true. But there were more-damaging repercussions to their decision. You see, in order to distribute water to the athletes in my care, some form of transportation was required. I couldn’t be expected to carry large amounts of water on my back like a serf. So the school provided a vehicle for the movement of the juice. They gave me a golf cart. The idiots.
As soon as the golf cart was in my possession, it never left my side. I’d drive it around campus, I’d drive it to class, I’d drive it into town, and I’d drive it in the snow and ice. I’d take it off-roading. It became well known to the local Wolfeboro Police Department, who continually fielded complaints from bystanders nearly mown down by my reckless driving. I’d take dates out in it; we’d go for beer runs or pick up pizzas. If there had been a drive-in nearby, I would have attended happily. I plagued my enemies with drive-by supersoakings. Pretty much the only place it didn’t go was onto the soccer field during sporting events. I was never too interested in the “work” side of the job.
I soon became known and hated as the kid with the golf cart. They were all getting used to the fashion thing, so this new wrinkle was a helpful reminder of my presence. And once they started to get used to the golf cart, I knew I needed to develop that also. So I started to modify it.
It was a shoddy, white 1980s Yamaha G-1 golf cart with a flimsy plastic roof and unimaginative design. But as this conveyance was now a major weapon in my arsenal, it needed to reflect my personality. I adapted the roof and turned it into a convertible. Now everyone could see me coming. I’d scour the want ads and Internet for suitable accessories. Soon it was slathered in decals, upholstered in leather, and outfitted with chrome rims on the tiny wheels. And for a final definitive fuck-you, I sourced and bought an actual Mercedes symbol and added it to the front of the grill, the angle of which changed with each subsequent crash. Oh yeah, I crashed the fucking thing at least ten times. It’s a miracle no one died. Probably because it could manage a top speed of about twelve miles per hour.
I avoided getting it taken away from me or getting kicked out completely by using a few of the manipulation strategies I had developed. I’d befriended the campus security guard, Charlie, whom everyone else treated like shit. I showed him total respect, because I knew he could help me. No one appreciated that Charlie was powerful. The same way valet parkers hold all the power wherever they work. They know where the bodies are buried. They see the sins of the managers. They appreciate how everything works. I quickly learned that the guy at the top of the tree wasn’t important, but the guy who could get you what you want was. And Charlie was no different. He was happy to give me the heads up when I’d pushed things too far and the shit was about to hit the fan. He was a useful ally.
He’d provide me with keys to certain parts of the building usually off-limits to the likes of me. Information about possible raids and searches were slyly passed my way. Certain professors were secretly on my side, too (they probably enjoyed how much I tortured Doucheborn), so I’d get passing grades if necessary. Some of my work was plagiarized or outsourced. Why not? If I’d shown even the slightest scrap of individuality or personality, they’d fail me anyway. They just wanted the answers on the page and to be left the hell alone.
I was also hacking into the dean’s e-mail, which helped me find out when things were getting peppery. Which was increasingly often. The golf cart was a great tool for getting me noticed, and it didn’t break any rules. But elsewhere in academic life, I was slightly more controversial. There was shit that would have gotten me kicked out instantly if it was discovered.
I had a roommate. As some kind of cosmic joke, he was from Germany. He liked to remind me of that fact as often as he could, usually in relation to the actions of his people against mine during the war. Grim, I know, but this was typical boarding-school humor. He was an obnoxious prick, not in the artful way I was, but just in a dickish, teenage-boy way. He enjoyed lighting individual pubic hairs on fire in front of me so he could revel in the smell of burning hair. I once sprayed Lysol on the flame just as he was about to ignite one, and he fireballed like Michael Jackson on the set of a Pepsi commercial. Needless to say, he wasn’t impressed. In f
act, he beat the shit out of me, so I decided our time together must come to an end.
I’d already recognized the influence of the medical unit and how their manipulation was a powerful force. Getting a doctor’s note for any number of conditions was easy, especially mental conditions. Look at the shit I did! Everyone was already calling me crazy; it wasn’t hard to get it documented. These mental issues progressed until I developed a powerful case of sleepwalking—or at least that’s what I told the campus nurse. I’d wake up in all sorts of crazy positions, sometimes with my hands around my roommate’s throat. I mean, we could have risked it and hoped it just went away, but I would have hated for something terrible to happen to him. With a sigh, they agreed, and he was shipped off down the hall, and I was allowed a dorm room to myself. The only boarder to enjoy this luxury. Once I had the place to myself, I started to get really inventive with my indiscretions.
Now, I will fully admit, I was fairly delusional at this time. I was flying. I was dressed like Patrick Bateman, driving beautiful girls around the campus in my pimped-out golf cart and now had my own room to take them back to. I soon developed this full New York–penthouse fantasy and started to remodel my dorm room to resemble something Trump would be proud to reside in. I brought in my own furniture and fittings. I had a Clapper to turn the electrical devices on and off. There was a refrigerator, neon signs, and air-conditioning. Way more shit than any of the dorm parents had.
I had my own food brought in. I never ate in the cafeteria; I needed time alone in my room to devise the next ludicrous scheme. So I got very friendly with the local Chinese restaurant in Wolfeboro, which would deliver to me, sometimes several times a day, in all weathers. The owner would slap snow chains on his Honda Odyssey and head out to Brewster to deliver my lo mein. I was putting his fucking kids through college. When I finally left school, I had MSG withdrawal sickness for a week. It was a pretty sweet setup but was missing a vital component.
Don't You Know Who I Think I Am?: Confessions of a First-Class Asshole Page 3