by Rich Roll
I fondly refer to New York as Disneyland for the alcoholic—a fast-paced zone of escape where nothing is out of bounds. Moving into a tiny midtown apartment with Stanford swimmer Matt Nance, who’d landed an analyst job at Morgan Stanley, I couldn’t wait.
But as work at Skadden began, my predictions of drudgery were confirmed. I’d underestimated just how mundane, tedious, dysfunctional, and unpleasant the position would be. For hours at a time, I hunched over a photocopier until my back ached. Weeks went by during which I was imprisoned in a windowless conference room filled floor to ceiling with hundreds of boxes of paper. There I organized documents in file folders by date or subject matter. If I was lucky, I’d be put in charge of “redacting” information from the documents. This heady task entailed covering up privileged information with strips of white tape from dawn through the wee hours of the night, day after endless day. But there was an assignment even more mind numbing—something called Bates stamping: a means of cataloging massive amounts of paper for purposes of litigation discovery. Today this chore is accomplished with computer scanners. But in 1989, it entailed hand-stamping consecutive numbers on each and every page of a document with an archaic prewar heavy metal hand stamp machine. Simple enough—unless you have to stamp hundreds of thousands of pages. Someone had to do it—why not a Stanford graduate?
The hours were long. Forget about making evening or weekend plans. Most of my waking existence was spent at the firm, where I traded my life for an annual salary of $22,000 and the privilege of being exploited by overstressed and sleep-deprived attorneys taking their many personal frustrations out on the underlings. On countless occasions I witnessed grown men reduced to tears or throwing tantrums in fits of exasperation. Once, an attorney even threw a heavy federal code book at my head.
I’m not trying to elicit pity—I was hardly working in a coal mine. It’s just a snapshot of big New York City law-firm life in the late 1980s—a reality far different from what is portrayed on television or pitched to unsuspecting law students, and certainly far different from the more gentlemanly practice my father had enjoyed. I wish I could say that I knew then that law school wasn’t for me, that I would seek out a more meaningful life. But that’s not really what happened. This was my first real job. And so I just assumed that my experience was normal—that this is what it meant to work in corporate America. It’s what men with educations like mine are supposed to do.
That said, I didn’t want what these attorneys had, a life that appeared to be misery placed atop piles of money. And I had no real desire for their approval. I simply didn’t care. I knew that a job well done would be rewarded with nothing beyond an increase in demand for my services.
And so when my phone rang, I just let it ring. Then I’d wait an hour or so before returning the call, knowing that by then the attorney seeking assistance surely would have found someone else to do his or her bidding. On many an occasion, I’d nurse a hangover by locking the office door, turning the lights off, and taking a nap. Other days, I’d leave the office for hours at a time, lingering over long lunches, strolling the streets of Midtown, or catching a movie, no one the wiser. If anyone asked where I was, I could just make up some story. But nobody ever asked. It was just too big a place to keep tabs on a low-level employee like me. And I took every advantage.
As my friend and office-mate Adam Glick was often fond of saying, “Dude, you are officially the worst legal assistant in Skadden history.” I can’t argue with his assessment, a perception he wasn’t alone in sharing.
But my other prediction also proved true. The banality of my professional existence was compensated for by a robust social life. I made great friends with fellow legal-assistant colleagues, falling into a tightly knit troupe of fun-loving, like-minded late-night party hoppers. We dubbed ourselves “Kings of the Low Budget Social Scene.”
A drunken wanderlust sent me deep down into the Manhattan nightlife underbelly, routing out as many downtown bars, avant-garde clubs, loft soirees, and degenerate after-parties as I could find. On one occasion I ended up in the basement of some decrepit and half-vacant downtown building watching midget bowling, otherwise known as “dwarf tossing”—a horrific and now outlawed relic of the fashionable 1990s New York party scene in which little people in padded Velcro costumes were literally hurled onto Velcro-coated walls by partygoers competing for the farthest throw. I’d read about this in Bret Easton Ellis’s book American Psycho but assumed it was literary license. Then I saw it with my own eyes.
Around this time, my roommate Matt Nance began training for the Manhattan Island Marathon Swim—a 28.5-mile circumnavigation of the entire island of Manhattan.
“You should do it with me, Rich,” Matt urged.
Swim all the way around Manhattan? Including the Harlem River? Yeah, right. Not only did it seem impossible, I had zero interest. No, I was too busy emerging from drunken stupors in strange apartments, wandering empty downtown crevasses in the dead of night, and subsisting on nothing more than booze, Gray’s Papaya hot dogs, McDonald’s, and Ray’s Pizza. Though I lacked the self-awareness to realize it at the time, I was adrift in mayhem, slowly destroying myself.
Then came the call. One day before classes began, I was informed that I’d been the last person accepted off the wait list for Cornell Law School. After a slew of rejection letters, it was my final opportunity to pursue a career in law. Given my less than stellar experience at Skadden, I’m often baffled that I chased this particular carrot. But at the time, it seemed like the right thing to do. Maybe some protective instinct had me realizing that it might save me from disappearing down the rabbit hole altogether.
Less than twenty-four dizzying hours later, I found myself transplanted to the curious rural hamlet of Ithaca, New York. Walking into a lecture hall to hear portly Professor Henderson regale a group of eager and wide-eyed “One L’s” on the less than fascinating tenets of tort law, I felt my sleep-deprived head spinning. As I scanned the room, it was beyond obvious that all the other students had spent the better part of the summer preparing for this day. While I was busy losing myself in the bizarre lower depths of Manhattan, my fellow classmates had diligently completed a robust reading list, arriving beyond prepared. The only thing I was prepared for was happy hour. Six thousand applications for only 180 spots. And I was the very last person permitted entry. The absolute bottom of the barrel. I couldn’t help but wonder if I’d just made a big mistake.
As it turned out, though, I genuinely enjoyed law school. I felt a sense of relief to be on a solid trajectory, any trajectory. I can’t say Cornell’s professors instilled in me a love for the law, but I relished the return to an academic environment and the challenges it presented.
I’ve always been sensitive to the weather, my moods taking their cue from whether the sun is shining on a given day. Call it “seasonal affective disorder” or just a lack of vitamin D, but at first the cold Ithaca weather precipitated as much depression as snowfall. Good thing I had a cure for this malaise. You guessed it. Alcohol.
At the time, I held out hope that getting out of New York City would be the perfect way to put my drunken exploits behind me. Not that I consciously admitted I had a problem. Rather, what I had was an impulse to control and enjoy my drinking.
But of course no matter where I went, I always brought myself with me, so it wasn’t long before I resumed my old ways. Things were exacerbated, in fact, by adding a car to the mix. It led to a few brushes with the law and the specter of a DUI arrest, which I narrowly dodged on more than a few occasions. And when my pastoral environs began to bore, I hightailed it back to Manhattan—the four-hour drive a small price to pay for a lost weekend soaked in booze.
Yet somehow I maintained decent grades. Nothing like straight A’s, but a solid B to B+ average. Okay, so I got a few C’s. But not many, even an occasional A thrown in from time to time to balance it all out. Not bad, I thought. Considering I was the last person admitted to my class, anything better than last place was a win as
far as I was concerned. So much for the unbridled ambition of my youth. That fire in the belly that had defined me in younger years wasn’t just dormant, it was all but extinct.
On one occasion, I swallowed a six-pack of Beck’s beer in my Volvo en route to presenting a paper on Russian constitutionalism. My class began at two o’clock in the afternoon. I might be an idiot, but I’m not stupid. I knew full well disaster was the most likely outcome. Then why? There’s no satisfactory explanation. Really no point in even asking the question. All I recall is a feeling of powerlessness to stop myself. After my fifteen-minute oration, the visiting professor from Moscow pulled me aside.
“May I have a few minutes with you after class?” he asked calmly, his thick Russian accent right out of a KGB spy movie. Alcohol coursing through my veins, I quietly drew my breath in deep and held it. Prepare for the gulag.
When the classroom emptied, I approached, braced and terrified, and he placed his hand on my shoulder. An odd smile spread across his face.
“Richard. This is a brilliant paper. A+. With your permission, I would relish the opportunity to present it to the Russian special constitutional convention in Moscow.”
Say what!? This special body of seven hundred comprised some of the world’s most savvy political leaders and legal minds, who’d been recruited to assist in redrafting of the Russian Constitution. Far from the inevitable humiliation, discipline, or even expulsion I was prepared to suffer, I was actually being rewarded. The messaging was, of course, exactly what I didn’t need: Drinking is the solution to your problem, not the culprit.
In the spring of my third and final year I received an offer to work as an associate at the law firm Littler Mendelson, a labor and employment outfit in San Francisco. Did I have a passion for labor law? Hardly. But the office was really nice and the salary decent. Good enough. And landing the job put my mind to rest about where I’d head next, allowing me to set aside any concern about grades and live out the rest of my law school days in a carefree alcohol haze.
On graduation day, I decided to commence my drinking within moments of waking up. Eight or so beers disappeared down my throat as I donned the elegant black and maroon cap and gown of the newly anointed Juris Doctor and drove to campus to greet my beaming parents and several of my friends. Welcoming the rare warm sun, I spent the early afternoon cocktailing through a variety of soirees, before heading to commencement at a beautiful outdoor amphitheater. During the procession I enhanced my already significant buzz by sneaking hits from a silver flask a friend had thoughtfully smuggled in.
As I watched my classmates summoned to the stage to receive their diplomas, it struck me just how much everyone seemed identical, part of an assembly line of newly minted lawyers issued by the Cornell factory. Despite the festive environment, warm weather, and every reason to feel nothing but gratitude, joy, and pride, I was struck by a sense of suffocating desperation. Is this all I am?
In that moment, I felt compelled to stand out in the crowd. So when my name was called, I kicked off my shoes and socks and walked to the stage to receive my diploma in front of three hundred or so students, faculty, and family—barefoot.
In my semi-stupor, I thought it was a stroke of genius. I’d shown how groovy and laid back I was. Pure California cool. What an idiot.
My friends and classmates cheered, or at least that’s how I interpreted their response at the time. But the professors on the dais were quietly unimpressed. And my parents were traumatized. When I joined them after the ceremony, I was caught completely off guard by the look of horror, embarrassment, and disappointment on their faces. The image is forever seared in my brain. What I utterly failed to grasp was that graduations are just as much for the proud parents as they are for the student—probably more so. The day was intended to memorialize a tremendous amount of sacrifice on their part. And so my mockery of the pomp and circumstance was more than injurious—it was devastating.
Over dinner that evening, they did their best to put on smiles and place the event in their rear view. But the damage was done. That night they bid me a muted good-bye, their departure laden with overtones of dismayed finality that seemed to say, You’re on your own now, big man. As I laid my head on the pillow, I wept until my stomach ached with grief, remorse, and regret.
Back in Palo Alto, where I planned to spend a quiet summer studying for the California bar exam, I shared an apartment off bustling University Avenue with Pablo Morales. Yes, the hero of my adolescence whose image adorned the walls of my bedroom was now my roommate and bar prep study partner. Still licking my wounds from graduation, I pledged to stay dry the entire summer. And I meant it. Focus on my studies, pass the bar, and begin anew. Unfortunately, I’d once again brought myself with me. And with Stanford playing host to the 1994 World Cup Soccer Tournament, and the around-the-clock revelry that came with it, staying sober became impossible. Needless to say, I failed the exam.
Though I was deeply embarrassed at having to retake the bar that February, being a young associate lawyer at Littler Mendelson was something of a solace. Unlike at Skadden, the people were nice—they respected the need for employees to have a life. And the pay was decent. I spent my days in a plush downtown office, with a spectacular view of Alcatraz and the Golden Gate Bridge, handling a very manageable caseload. Still, I just couldn’t summon much interest in labor and employment law, and I spent hours wistfully gazing through my window at the afternoon fog rolling in across the bay. Miraculously, I’d survived law school and managed to land on my feet in a pretty darn good place. I should be happy, I told myself. So why do I feel this way? What is wrong with me?
San Francisco isn’t New York. But I was back living in an urban environment. So it was time to pick up where I left off. I moved in with Gavin Holles, a banker and former LSU swimmer whom I’d once competed against in the 200-butterfly. Gavin is a great guy and made for a good roommate. And if I had to choose one word to describe him, it’s tolerant. Together we had plenty of good times enjoying the San Francisco nightlife, barhopping our way across the Marina. But when it came to me, Gavin would soon discover that he got more than he bargained for.
Here’s a typical weekday snapshot of how I rolled in 1995. Honing the skills I developed at Skadden, I’d generally perform the least amount of work possible, fulfilling only the bare minimum of expectations. On many occasions, I’d leave the office with no goal other than to aimlessly walk the streets alone. Leaving my jacket draped on my desk chair gave the appearance that I might just be down the hall, working in a quiet conference room or perhaps meeting with a client. Around five o’clock, I began staring at the clock and evaluating my environment in an effort to determine exactly how early I could duck out. En route to the Marina from the financial district, I’d generally stop by my favorite liquor store, where I’d pick up four large twenty-two-ounce Sapporo beers and one bottle of Sauvignon Blanc. For the drive home, I’d usually drink at least two of the Sapporos, hiding the empties under the seat. The remainder of my stash I concealed in my soft leather satchel. That way, if Gavin was home when I arrived, I could sneak the booty into my room without notice. In other words, I began to hide my drinking.
After drinking another Sapporo in the shower, I’d head to my bedroom. Door closed, I’d turn the television up loud to obscure the sound of my wine cork popping and proceed to finish my stash in privacy as Gavin ate dinner alone in the kitchen. With my head now fully buzzing, I could finally embrace the night and all the adventure it might hold.
I convinced myself that Gavin had no concept of just how depraved I’d become. Of course, he was well aware. In later years he confessed that he knew just about everything. He just decided to keep it to himself.
Ironically, during the two-year period in which I shared an apartment with Gavin he competed as an avid Ironman triathlete and open-water swimmer. So while I lay passed out in the next room, Gavin would generally awake before dawn to train. On the weekends, he’d leave town to compete in this race or that, often winni
ng or placing in a variety of long-distance ocean swims or other multisport events.
Gavin would cajole me: “Come on Ricky, you should do this stuff with me, I bet you’d be pretty good.” He liked to call me Ricky, a nickname I earned one night after overdoing it on Sambuca liqueur. Sambuca, rocker Richie Sambora—similar-sounding words, you get the idea. I hate that nickname. But it stuck.
During a long weekend spent with friends in a house on Lake Tahoe, I remember waking up one morning around 10 A.M., wildly hungover, to find Gavin, along with his buddy Greg Welch—an Ironman world champion—and a bunch of other triathletes hanging around the kitchen in their cycling attire.
“Wow, you guys are up early. Headed out for a ride?” I asked.
“Just finished, mate,” Greg replied in a friendly Aussie drawl, taking in my pallid appearance with a wry smile. While I was passed out, the crew had already logged a ninety-mile loop around the lake. Part of me wanted to vomit just thinking about it. But the other part felt an entirely different emotion. Shame. Why can’t I be more like that?
CHAPTER FIVE
WHITE SANDS AND RED STRIPE
Hitting Bottom in Paradise
In the spring of 1995, while I was still living with Gavin in the Marina, I fell in love with Michele, a native of Palo Alto with green eyes, long legs, and equally long, dark hair. Of course, we met in a bar. And predictably, I was drunk.