The Coolest Guy I Ever Met

This is another in the series of essays I wrote about five years ago about extreme people I've known. This guy asked for his name to be changed, so it has been.


It’s instructive to see which icons of cool from the Fifties and Sixties have survived with their image intact, and analyze why. James Dean, because he died young and beautiful, was instantly immortalized as the original Rebel Without A Cause. No embarrassing old age full of faux pas, lawsuits, and revelations from jilted lovers to sully his youthful purity. From a distance Dean looks good, but upon closer examination, it’s hard to find much beyond the handsome face.

Marlon Brando, unlike Dean, was a real rebel, and an actor of originality and power, who followed his own path offscreen as well. He achieved greatness early on as Stanley Kowalski, then again in “On The Waterfront” and “The Wild Ones,” and later as the Godfather. But he survived even longer to become old and corpulent, as well as an icon of family dysfunctionality. His light might shine brighter had he too died young.

Lenny Bruce is still considered cool, although dying of a heroin overdose is hardly considered cool these days. He, too, was a rebel and a noncomformist. Jack Kerouac has faded a bit; today kids aspire to be more than writer/hobos. (Writer/millionaires might be more in keeping with current fashion.)

Ken Kesey was immortalized twice – once as the author of “One Flew Over the Cuckoo’s Next”, and once as the hero of Tom Wolfe’s “The Electric Kool-Aid Acid Test.” Kesey still has a following, but he is more of a cult figure, meaning his following is small.

The Rat Pack – Sinatra, Martin, Davis et al – have been considered cool again for the past six or eight years, after a long eclipse. Perhaps the true measure of coolness lies in the number of people who try to imitate you. And millions make the trek each year to Vegas, a place Frank and Dean made glamorous.

Elvis, also officially passé by the late Sixties, has also enjoyed a recent resurgence. (Among the faithful, of whom there are many, he was never out of favor.) But he, like Brando, lived long enough to become an overweight self-parody, unable to function in the prison of his own fame.

The Beatles, the group symbolic of all that was the Sixties, now seem more icons of youthful exuberance than of cool. But when they first burst on the scene, with their long hair and high energy music, they seemed to represent a new, revolutionary kind of cool. In retrospect, Ringo seems merely lucky, a winner of the rock and roll lottery. George, a talented musician and guitar player, retreated into a mysticism which now seems merely mindless. John is still revered by many, but he was always a little too earnest; it’s hard to be cool when you’re a primal scream kind of guy. Paul was the Beatle who came closest to being cool. If not quite the musical genius that John was, Paul was the only one who seemed able to separate himself from his fame, and actually enjoy it, at times even with a twinkle in his eye.

Jim Morrison and Jimi Hendrix never lost their cool images, but if you’re too drugged out to be in full control, that’s not really cool. Both were truly great musicians, but both were also, surprisingly, crippled by shyness at various times in their lives. Morrison needed to get drunk before he could go on stage, and Hendrix was reportedly so shy in his youth that he went through junior high school hardly talking to anyone.

The closest thing the rock scene has to an enduring icon of cool is Mick Jagger. If his image as rock’s bad boy/street fightin’ man turned out to be a pose, well, that’s okay because being cool means not taking yourself that seriously. He ended up as a jet setter (when that phrase was in vogue), as one of the Beautiful People (when that phrase was in vogue), and as a very rich man (which is always in vogue). Jagger has also been one of the all-time great womanizers. But he has always seemed more boy than man, and now he seems a little too desperate to remain Peter Pan. (He still gets the girls, though, so who can blame him?)

It’s a lot easier to be considered cool if you’re a pop culture figure rather than a politician, but JFK, the leading political icon of the era, has survived all the passage of time with his cool totally intact. All of the stories which gradually emerged after his death, some originally meant to discredit him, have only served to augment the glamorous, even slightly decadent aura which now surrounds him. He did everything with style, and under the most daunting conditions.

Of course, it’s easy to be cool when you’re famous. What does it take to be cool when you’re not? We all had people we looked up to in high school or college, people we considered cool. But what was it exactly that made them that way? “Cool” is a certainly word that allows for a lot of wiggle room, but there are several qualities which must be included in any definition.

You have to be smart, or, at the very least, be able to hide your stupidity. You should be up to date on matters of taste and culture without being trendy. Ordinary SAT-type intelligence doesn't cut it; some sort of charm is required. You have to be witty, or somehow clever. Creativity is a huge plus.

It helps to be courageous. There is a certain romance, a certain intensity associated with the proximity of danger. The word "tragic" always adds to one's allure. (Evel Knievel managed to attract a fan base without anything other than that going for him.)

Calm unflappability is called for. Hysteria is the opposite of cool. Hemingway defined courage as grace under pressure. This is what made James Bond so cool.

You have to be able to keep a secret. Blabbing is the opposite of cool. You should have a good poker face when that’s called for.

Cool is also defined by what it is not:

You can't be needy. Needy people always need reassurance, and they always seem pathetic.

You can't be temperamental. Blowing one's stack is the opposite of cool. (Did you ever see the hero of a movie throw a tantrum?)

You have to be an original. No one who ever tried to imitate anyone else was cool. The people they imitated were the cool ones. Likewise, you can't pretend to be anything you’re not. You can't try to act richer than you are, or smarter, or tougher.

You can't try too hard. For coolness is like quicksilver: it's an evanescent quality which disappears the moment it's striven for. You either have it effortlessly or not at all. A lot of people pride themselves on being cool; but they’re not, for that reason.

There are two very superficial criteria which help in being perceived as cool. The first is looks. It's not fair, and it doesn't even make any sense, but if you're not attractive, people generally won't perceive you as cool. (One sure sign of "coolness" is when your poster is a big seller. No poster was more ubiquitous in the late Sixties than Che Guevara's. Most people had the vague idea that he was associated with Fidel Castro and leftist politics, but that's all they knew; they bought the poster because Che was handsome in a vive la revolucion sort of way. If Fidel had looked that good, people would simply have bought posters of him.)

The second superficial criterion is age: you can't be too old. This is no more fair than the looks criterion, but if you're old, people just don't perceive you as cool. (Witness James Dean, whom we'd long since have forgotten had he survived his twenties.) Coolness seems to go hand in hand with the insouciance of youth. Would the JFK/Camelot legend ever have been born if he had looked the way his brother Teddy looks now, and if Jackie had resembled Mamie? Would he have inspired all those young people to join the Peace Corps?

The word “cool” tends to evoke images of jazz musicians in smoky dives, or rock stars with nonchalant attitudes towards everyday responsibilities. It has slightly hipsterish connotations, and has a slightly more blue state than red state feel to it. But this needn’t be: James Bond was the ultimate icon of cool, and his instincts were obviously more red state.

Perhaps the best measure of cool is how often a person makes you think, wow, I could never have done that. Or, wow, how did he ever think of that? Or, wow, he handled that situation perfectly!

The coolest guy I ever met (though he is no longer young) is George Smith. He is a six foot one, muscular 180 pound black man. He is lean and handsome: his forehead is high and broad, his cheekbones prominent, his jaw square. He has the kind of face that people often refer to as “noble”. He speaks in a well-modulated baritone. He looks as if he could have been picked for the role of “cool guy.”

But this wasn’t always the case.

George was born in Washington D.C. in 1952, the son of two high school teachers. He showed an early academic and intellectual bent. At age fourteen he took the chemistry AT and scored 800; at age fifteen he took the physics AT and got another 800. He was even selected to appear on a quiz show while still in high school. His SATs were 722 Verbal and 774 Math.

George also ran track in high school, with no particular distinction. Part of the reason he didn't excel at athletics in secondary school was because by the time he was a senior he stood five foot six and weighed 120 pounds. If, at this point, he sounds more nerdy than cool, it’s because he was. (Even cool guys have their larval stage.)

He entered Harvard at age sixteen in September of 1969, and didn’t reach his full size until spring of his sophomore year. (As one high school acquaintance said when she ran into him in college, "You're little Georgie Smith?!")

George, having discovered his newfound attractiveness to women, was in no hurry to graduate. He took a year off from college in between his junior and senior years to work for Eastern Airlines as a flight attendant. Training base for the attendants was in San Juan, Puerto Rico. The ratio of women to men was roughly four to one, and men were mostly gay. Thus George and his two roommates anointed the base “Candyland”.

George majored in biology, and graduated with a respectable 3.2 average, below what he got in high school, but good enough to get into Georgetown Medical School, where he planned to matriculate in the fall of 1974. But that summer. George heard about a method of making money by counting cards in blackjack. He spent much of July and August in his basement practicing. (I once saw him take four decks of cards, shuffle them, place them all face down on a table, and pick them up two at a time, leaving the last two cards face down, all in sixty-three seconds. He then said within a small range what the two cards added up to. It wasn't trickery, just card-counting.)

That September, instead of going to medical school, George went off to play blackjack at the casinos instead. His first year, he made roughly $100,000, big money for a 22 year old back in 1974. George's mother had the expected reaction when "my son the doctor" suddenly morphed into "my son the card player." So, mostly to keep his mother happy, George also applied to law school that year.

The following September, George entered Harvard Law, but still spent much of his time playing blackjack; that year he made $135,000. During the next two years of law school George spent a lot of time in places like Monte Carlo and Panama City. But by 1976, the casinos had wised to the counters. Dealers now used six decks of cards, then reshuffled and started over again when they were only halfway through the six decks. This eliminated most of the counters' advantage. They also started to ban known counters from their casinos. George himself was never banned. In his words, "Racism worked in my favor. Everybody figured a black man would be too stupid to count cards."

George never graduated from law school because he never wrote two required papers. He just couldn't bring himself to finish them, because his heart wasn't in law. So he hung around Cambridge for three extra years, reading voraciously (and omnivorously), and working out, living off the remains of his blackjack earnings.

On every university campus, you’ll find post-grads who haven’t decided what to do with their lives. They are for the most part lost souls who can't seem to cut the umbilical cord attaching them to the warm friendly environs of their college. They're usually fairly bright -- they wouldn't love academia if they hadn't done well in school. But they are usually missing the gene for ambition, or toughness, or whatever it takes to face the real world beyond the campus. But George was different.

I met George in the fall of 1981, at the tail end of his sojourn in Cambridge, at the Harvard pool. I heard someone ask, “Are you John Craig?” I looked over and registered the following three impressions within the space of about a second: first, black; second, a lot of muscles; and third, very handsome. It occurred to me that if I had met this guy before, I would have remembered him, but I couldn’t place him. He introduced himself, and explained that he knew my brother and sister.

We chatted for a while, and it turned out that he knew all about competitive swimming, which surprised me, as swimming was a lily white sport at the time (it’s still mostly white). At one point he quizzed me on what some of the winning times had been at the 1964 Olympics. He seemed impressed that I remembered, so I turned the tables and tested him, certain he would not know the answers. George answered every question accurately. (Some swimmers have a surprisingly hard time remembering their own best times, and very few people in the sport know much of its history.)

As we walked out of the building, we heard some police sirens wail, and saw some flashing lights pull up to the front of Lowell House, where some young black men had congregated. George said lightly, "Ah, some of the brethren, in need of a jailhouse lawyer. Maybe I should offer my services."

I ran into him a few more times in the next couple weeks, and we were soon friends.

In those days, George gave off the air of a charming ne'er-do-well. At age 29, he had never held a steady job (blackjack not qualifying as "steady"), was unsure what he wanted to do (he was only sure of the many things he didn't want to do), and was running out of money and time. But with lots of energy, a sense of humor, and time on his hands, he was the perfect companion.

He was certainly a new experience for me. I had never expected to meet a black guy who knew as much as I did about swimming, and who was interested in SAT and IQ scores as much as George seemed to be. At one point I said to him, “You’ve been, uh, quite a surprise to me, I mean, uh….” He finished my question for me: “You mean why aren’t I like all the rest of them niggers?” I replied, “Uh….yeah.” He just shrugged, “I don’t know, I’m still trying to figure all that stuff out myself.”

On another occasion he asked me, “Have you ever slept with a black girl?” I replied that I had, once. He then asked, “Did you do it sort of just to see what it was like, or just to be able to say you’d done it?” I said, “Yeah, pretty much.” He seemed pleased by my honesty.

Most of our time was spent trying to meet girls. At the time it seemed our main purpose in life was to meet girls and get laid. One is never going to achieve much worldly success with that as one's primary goal; but it can be a fun way to spend a year or two.

Sex had always ranked high among my priorities, but I had never thought of it as a sport until I met George. I got my first inkling of this one Friday night when he suggested we go to a party he had heard about. When I explained that I had a date with Joanne, he looked at me as if there was something very, very wrong with me, and asked, incredulously, "What do you want that for? You've already haaad that." He was mostly joking, but it was still a new point of view for me.

Often, after one of us went on a date, we would perform a postmortem, analyzing what had gone right or wrong during the evening. Occasionally we would try to pinpoint the exact moment we knew we were going to score. George would often jokingly tell me what I would have done at each stage of the date had I been a "real man."

Although George would often kid me about how I should be more assertive with women, his own approach was anything but. Unlike most womanizers, he never lied to them about himself or his intentions. Although he was always polite and usually flattering, he never pretended to be even remotely in love with them. He would basically just present himself as a scalawag, and make a sort of joke out of the entire courtship process. The message he sent was always: this is what I want (your body), we both know it, and I'm not going to try to hide it. My role is that of the rake, yours is that of the potential "victim," but as long as we're both playing these roles, we may as well both have a few laughs, whether or not you succumb. As a result, he never had ugly breakups or recriminations afterwards. He even kept in touch with a few old girlfriends.

Almost all of us have a little bit of the stalker inside us, but George was strangely free of jealousy. One time he had chased a girl for weeks, taking her out to various restaurants and spending a fair amount of money in an effort to land her. It eventually became apparent that she liked me more than him (a rare occurrence) even though I had shown no interest in her. So one evening when we were all out together he said, "I'm tired. I'm going back to bed. But you two ought to go out, go somewhere." Then he leaned over to me, and murmured, "It'd be a shame if this thing went entirely to waste."

George seemed to enjoy the chase as much as the conquest. And it was always fun to watch him on the make. George seemed to know at least a sentence in virtually every language and whenever he met a woman from the country where it was spoken, he would trot it out; they would inevitably be pleased. One of the games he used to play was to challenge a woman to a running race, but with him running backwards. (He usually won.) He gave off an air of boyish enthusiasm and exuberance, but since it was combined with a very real underlying sophistication, the approach usually worked.

All young black men have a hurdle to clear when meeting new white people: they must prove they're not dangerous. George was extremely good at putting white people at ease. (I’ve seen him do it hundreds of times.) It may be unfair that the burden of proof was always on him, but he seemed to bear it lightly. One time I was out on a date and George came along for dinner. He ended up paying, so I said to my date, "Well, I guess you're George's date for the evening." George looked at her, and asked, "Well, have you ever dated a minority before?" She replied, "No.......Oh wait a second, I dated a Chinese guy once. Does that count?" George pursed his lips, considered this for a moment, then said, "Nah.....their SATs are too high. To qualify as a bona fide liberal you have to have dated one of us sub-humans."

If George was late, he would sometimes say, "Sorry, I operate on CPT." When asked what that was, he would reply, "Colored Peoples' Time. You know, we're always fifteen minutes late for everything."

Occasionally he would tell people that his Muslim name (this was back in the day when it was more common for blacks to change their names) was "Umgawa Acholi, which translates directly from the Swahili as, 'Bold warrior with great hook shot'."

Every now and then George would break into Ebonics just for effect; but this merely emphasized that he was in fact as far from the ghetto as the white people he was talking to. Every now and then he would talk about his "boys from the ghetto," but this never fooled anybody -- and wasn't meant to. (While George was capable of self-deprecating racial asides, his political loyalties veer decidedly left.)

Blacks with George's academic pedigree have another hurdle to jump: proving they are smart, and not merely products of affirmative action. Four or five minutes of talking to George is enough to convince anyone of his brightness, if not brilliance. He can converse with anybody on whatever subject interests them, and do so in a way that keeps them involved.

He's able to do this for two reasons. The first is that his range of interests is unparalleled. He knows a number of sports: swimming, track, football, basketball, boxing, and tennis. He also knows science, history, music, politics, law, and finance. And these are subjects he knows in depth; he has a smattering of knowledge about just about everything else. (One of his parlor tricks back in those days was to challenge someone to name a piece of classical music he couldn’t hum. The only time I ever saw him stumped was when a clever girl once asked him to hum Stravinsky's tuneless "Rites of Spring.")

The second reason is he is a good listener. Calling someone that is usually a jokey way of saying that he has nothing else going for him. In fact it's a rare skill; most people just wait their turn to talk (and some don't even wait for that). George actually thinks about what the other person says, and responds in a way that shows he has listened.

If nobody else is taking the lead in a conversation, he will fill in the silence, but if somebody else wants to be the center of attention, George is content to let him. His lack of neediness is demonstrated by the fact that it was only with extended cajoling that I got him to agree to this article, and even then only with a pseudonym. (Now that's cool -- being called the coolest guy, but not even wanting credit for it.)

Another unique thing about George was that he would never reply to a question with just a phrase or word: he almost always spoke in complete sentences. Yet he somehow managed never to sound stilted.

At the time it occurred to me that he was like a character out of a Ross Thomas novel. (Thomas’s novels always featured super-slick, clever, good-looking people who were well acquainted with the seedier side of life, and were inevitably involved in schemes of dubious legality.) Card counting may not strictly be illegal, but frequenting casinos while doing something they would expel you for does have a certain aura.

One of the defining traits of the characters in the Thomas novels is that none of them ever seem to suffer from self-doubt, or indulge in neurotic worries. George certainly never seemed to fret over how he might be coming across. Most guys would be afraid to go on about how another guy swims beautifully for fear of sounding gay. George would praise my butterfly effusively, even to other people, and then have me demonstrate. Some of this was done in an effort to attract girls, but he also had me do it for his mother one time, and a buddy another time.

George himself has dabbled at a number of sports. He has the build of a natural athlete, but sometimes it seems he practices a sport just enough to appreciate how good a champion has to be. He was a creditable swimmer: after two years of practice starting at age 26, he swam a 50 yard breaststroke in 30.7. He began running again at age 28 and ran 200 meters in 23.2, quite fast considering his limited background in the sport. In his thirties he took up tennis and attained a 5.0 NTRP ranking, good enough to play on the Volvo Satellite Tour. If possible, he'll compete with someone much better than he is, just to see what it is like. He once played an out of shape (and older) Tim Gullikson in tennis, and was beaten soundly. That became one of his favorite tennis stories.

George, like most charmers, had a lot of prepackaged routines; but he was also very quick-witted. Several times during that year he came to our house to have dinner with my family; he always managed to charm everybody. One time, after he had just said something clever, my brother said, “George is really the master of the mot juste." George, who had just held out his plate and asked my mother for some more gravy, nodded his head and said, "That's right -- more juice Mrs. Craig, more juice please."

There was one Asian-American woman whom George liked at the time, Tomiko. One time he expressed frustration with his inability to read her. I replied, “You know us Orientals, we’re inscrutable.” (I’m half-Japanese.) George replied without hesitation, “Take out the 't’ and you’d have Tomiko.”

George isn’t always funny; sometimes he’s downright boring. It’s not as if being around him is like being entertained by a nonstop movie with an exciting hero. But I’ve also never seen him at a loss for words; and the other difference between him and most people is that he is, fairly frequently, capable of creating magical moments.

That fall, George was hired as a bond trader by one of the major Wall Street firms (mostly because he had been a card counter), and I went to business school in New York City.

New York City was a new experience for both of us. In 1982, there were still a lot of homeless people on the streets. One of them, obviously crazy, came up to George one time and screamed, “Bring back the Dodgers,” George cried out, “Yeah! Bring back the Brooklyn Dodgers! Jackie Robinson! Yes!” He then turned to me and said, “Where else but in New York City can you just start up an intellectual conversation with someone in the street? The give and take here is just so stimulating!”

One thing George did not like about the city was the prevalence of smoking. Although there is a rule against smoking in the subway, people would often smoke anyway, and as often as not, the smokers were black men. Whenever George would be stuck in the same car as one, he would go up to him and say, “Don’t mean to scare you brother, but the Man is in the next car.” The smoker would usually quickly
extinguish his cigarette and reply, “Thanks, brother.”

After I graduated business school, we roomed together for two years in Brooklyn. We lived at the corner of Third Street and Fifth Avenue in Park Slope. At the time, Fifth Avenue was the clearly demarcated boundary between the gentrifying (whitening) area and a much poorer (primarily Puerto Rican) area, much as 96th Street divides the Upper East Side of Manhattan. Neither of us ever felt threatened, partly because we were young men, partly because we both had protective coloration (I look Hispanic). Once after I described to someone where we lived, George added, “Yep. The neighbors are still trying to figure out whether we pushed the boundary in or out.”

We continued to chase girls, though at a less furious pace. One time George, on the way home from work, saw a girl he thought attractive. He just followed her into her subway car, pretending he was just on his way home himself, and managed to strike up a conversation, which turned into a brief affair.

Another time we went out to dinner with two European girls who didn’t speak English very well. One of them said that the reason they were having dinner with us was because we were “interesting.” George furrowed his brow, then asked, in mock seriousness, “Hmm. So looks and wealth aren’t enough for you, eh?”

By this point, though, he seemed to be spending as much time evading girls as chasing them. I would often hear him answer the phone, tell some girl he was just on his way out the door, then go back to reading the newspaper.

Eventually, in 1987, he got married, to a beautiful Harvard Law School grad with a good sense of humor.

By the late Eighties, bond traders had attracted some publicity about the amount of money they were making. (Although it has been dwarfed since, this was the “Decade of Greed,” when Tom Wolfe wrote “The Bonfire of the Vanities” and the phrase "Master of the Universe" was in vogue.) Tom Brokaw did a television special on the subject, and was interviewing some young traders at George’s firm; the subtext of the show was how sinful it was for such young people to be making so much money. Because George was well-spoken, his firm had offered him to NBC as an interviewee. When Brokaw asked him how much he made, George replied, “I make enough to feed and shelter myself, and to contribute to organizations which help feed and shelter others, and then have some left over. But I make only a small fraction of what a network anchorman makes.” To Brokaw’s (and NBC’s) credit, they didn’t edit the comment out.

Fast forward twelve years, to 1999. I hadn’t see George for some time but he called and suggested we go to Seville to watch the world track and field championships. The meet was exciting; among the other races, we got to see Michael Johnson set the world record at 400 meters. The entire week, the locals -- many of whom had seen few blacks before -- would ask George, who looked much younger than his 46 years, if he was there to compete. George would say no, and that would end the matter. But towards the end of the week, a young boy approached him and asked the same question. George replied in Spanish, "Yes, but please keep it a secret. I don't want to be besieged by autograph seekers." The boy, of course, immediately told all his friends, and George was mobbed. When they asked his name, he replied, "Michael Johnson."

On another occasion, we ate dinner in a restaurant where a giant screen behind the bar was showing Ivan Pedroso of Cuba winning the long jump that evening. Pedroso, in the half light of the evening, bore a passing resemblance to George. The other diners looked at the screen, and then to George, and back at the screen. They started murmuring to each other, and pointing at him. George stood up, did an imitation of a long jumper on the dining room floor, and raised his arms in triumph. Everybody applauded him, and several women even came up to kiss him. He shrugged as if merely accepting his due.

One evening we went to Marbella so George could go to a casino. He drove seventy miles an hour on a two lane highway with no divider (about the same speed as most of the Spanish drivers). I suggested he slow down. He laughed and said, "If we get in a head-on at fifty, we're still going to die, so what's the difference?" (From that point on, I drove.) Later in Marbella, a cab driver drove us literally sixty miles an hour down a city street. I told George to tell him to stop, and George just laughed. The danger didn't seem to bother him.

Before we went to the casino he put on a collarless buttoned shirt, a sport jacket, and patent leather shoes. I told him he looked like a typically overdressed black professional athlete; he just snorted. When we entered the casino, it was immediately apparent that I, in polo shirt and slacks, was underdressed. Americans generally dress for casinos as if they're going to a Little League game; Europeans, as if going to a fancy ball. All the women were in evening gowns, the men in sports jackets or suits. George wandered around a bit, putting down some chips at a blackjack table, a roulette table, and a craps table, but didn't sit down. He seemed to be looking for something.

Suddenly he pointed at a doorway and said, "That's where we want to go." The high stakes room seemed to be filled mostly with blackjack tables. The minimum bet was the equivalent of roughly thirty dollars in pesetas. George sat down at one of the tables and started playing. He gradually raised his bets till he was betting the table maximum of roughly four hundred dollars a hand. The entire time he made jokes in a sort of guttural Spanish; I don't know what he was saying, but it must have been funny because everyone, even the dealer, was laughing. People started to gather round to watch him. After a while George tilted the seat next to him against the table, indicating that he wanted to be dealt two hands on each round. This meant he was betting eight hundred dollars a hand. By this point a fairly large crowd had gathered around. They were obviously wondering who George was. Meanwhile, George continued his patter.

I had never seen anything like this; I couldn't have imagined losing that much on one hand of cards. After an hour or so, we walked outside to get away from the smoke. I said, "There's a reason they set scenes from both 'Thunderball' and 'Diamonds are Forever' in casinos." George just laughed and said, "Once you've hung around these places long enough, they seem like sad, pathetic places that attract a lot of degenerates. But it is sort of satisfying to draw a crowd.

We returned to Seville to watch the last couple nights of track. After the meet each evening, we'd get a bite to eat, then take a taxi back to the hotel. We ate late, partly because we were trying to stay on East Coast time, and partly because that's the Spanish custom. The Spaniards would just hang out at bistros and outdoor nightclubs until the wee hours of the morning. I commented, "I can't believe that these precious people who sit around smoking till all hours of the night are the same dynamos who conquered a third of the world back in the 1500's." George replied, "Well, that was before they had invented the disco. You know when they invented the disco, right?" When I said I didn't, he replied, "Fifteen eighty-seven." (The Spanish Armada was defeated in 1588.)

Two years later we took a trip to Las Vegas. By this point, George, by now retired from his job as a bond trader, had done extremely well for himself trading stocks on his own, multiplying his net worth several times. This was reflected in the kinds of bets he now made: up to $10,000 a hand in blackjack, and similar amounts at the craps table. Yet neither winning nor losing seemed to have much effect on him. (James Bond also bet large sums, though he always seemed to win. The true test of his coolness would have come only when he lost. One suspects that he would have been as nonchalant as George.) One time I saw George lose $20,000 on one roll of the dice at the craps table. When this happened, all the spectators and employees who had gathered around the table looked at George, to see what his reaction would be. He just made a disgusted expression, shook his head slightly, and placed another bet.

George was now officially considered a “whale” at the casinos, and was treated as such, with all the attendant attention and amenities. He didn’t act like a typical whale, though. He often dressed in a t-shirt and shorts. And though his hosts would have fawned all over him had he chosen to boast about his own exploits, he was more interested in listening to their stories about Sin City.

At this point the suspicion might arise in the reader's mind that George has a monkey on his back. (The definition of an addict is someone for whom life seems bleak and boring if he does not have any chips on the table.) But although George lives in New York, he has never been to either Mohegan Sun or Atlantic City, places he would surely have visited had the monkey taken grip. He just likes going out to Vegas every now and then. And the amounts he bets never pose any threat to his financial well-being.

The Stratosphere Hotel and Casino in Vegas features a thrill ride, the Big Shot, which starts at the top of the 921 foot high casino roof and goes up a tower to a height of 1081 feet. Riders are strapped into their seats, and experience 4G’s on the way up, then, after a sickening pause, go into freefall. George suggested a ride. I am afraid of heights, so I demurred, despite his insistence that it was fun. (He had been on it several times.)

Back in Cambridge, I had always thought of George as being very similar to me, with similar interests and tastes. It was at this point that it struck me that George and I were in one way fundamentally different: while I was a coward, he was absolutely fearless. The types of phobias that bedevil most of us: heights, public speaking, swimming in the ocean, snakes, etc., never seemed to elicit any sort of reaction from him. I once asked him, what scares you? He furrowed his brow, thought for a few seconds, and replied, "Nothing I can think of, really." I said, come on, there must be something: spiders, snakes, something? He then grinned and replied, "Aremissoft going to fifty. Now that would scare me." (He was short Aremissoft at the time.)

George is not macho. He doesn't boast, or strut. He doesn't ever try to act tough, or pose as some sort of hard case. He has never been in a fight (though he did box in the Wall Street charity matches one year). Nor does he regard fearlessness as a particularly admirable trait. He simply lacks the fear response. (Is this a crucial ingredient of "cool"? It certainly seems to help.)

One thing that does get George’s motor going is the sensation of speed. He drives a Mercedes SL55, and has driven it well in excess of 100 mph. (George drives fast, gambles, and was at one point a womanizer – just like James Bond. But these are things that any rich man can do, and coolness is not a commodity that is for sale, otherwise any fool could buy it.)

There is a term used in psychology textbooks, “organic sociopath,” which connotes someone who because of his physical and neurobiological constitution, is more likely to end up as a sociopath. These people are much harder to socialize, simply because they are organically less inclined to feel fear: they cannot be scared into behaving themselves. (I’ve actually known a couple of stone cold sociopaths, who were quite “cool” in their own way, but I was disinclined to give them the nod for this essay for all the obvious reasons.) Such people also tend to have extremely high thresholds of excitement – it takes more to get their adrenalin flowing. George, brought up by two loving parents, is definitely not a sociopath. (In over twenty years I have yet to catch him in an outright lie.) But he is probably an organic sociopath.

The way George traded stocks reflected this fearlessness. During 2001, on three separate occasions he put his entire net worth into one stock. (This didn’t mean he put his entire portfolio into one stock: since he was always fully margined, he always had close to two hundred percent of his net worth invested.) Once again, the specter of a possible gambling problem (albeit in more legitimate form) raises its head. But the defining factor of George's trading was that he always did his homework very, very thoroughly -- which is why he had the confidence to make such bets. He would not only examine a company’s books, he would get to know its CEO, its CFO, its head of research, and its marketing manager. Then he would speak to its competitors, to find out what they thought of it. He would speak to both its suppliers and its customers. And he would talk to independent analysts about it.

George wasn’t necessarily long the stocks he traded; sometimes he’d be short to the maximum extent possible. At one point in 2001 he told me to short the telecommunications company Winstar, then trading at fifteen dollars. I had shorted some tech stocks during the bubble of 1999, and had gotten burned, so was reluctant. But he kept me on the phone for half an hour, saying that there was no way this stock could survive, given its massive debt service, and that I had to short it. He had analyzed the amount of debt they had backwards and forwards, and had even sent off a fax to me and a few other friends about it, in which he described Winstar’s huge debt as a “trap door” through which it the company would inevitably fall. I eventually shorted some. George, of course, was as short as his margin requirements would allow.

When the stock hit nine dollars, Jack Grubman of Salomon Smith Barney, who was the foremost telecom analyst in the Street at that point, came out with a strong buy recommendation. I phoned George and asked him about that. George replied, “Do you have any idea what Jack Grubman’s life is like? Every single mutual fund manager on the Street wants a piece of his time. He’s constantly tied up with all sorts of internal managerial meetings at Salomon Smith Barney. He has a huge staff to supervise. There’s no possible way he can do his homework thoroughly. And all of this is not even to mention that his recommendation can’t be trusted since Salomon is Winstar’s investment banker. Do you think they would jeopardize that relationship? You should short more now. That's what I'm doing.” When the stock hit two dollars and forty cents, I asked George if it was time to cover in. He replied that he was shorting even more at that price.

Soon after, Winstar declared bankruptcy, Jack Grubman was discredited, and George got even richer.

There are four cliches that one constantly hears on Wall Street. The first is that you have to be a risk-taker. Everybody pays lip service to this idea; but almost nobody takes big risks with his own money. (Taking risk with other peoples' money is just not the same thing.) I've heard guys go on and on about how you have to be able to stomach risk to work on Wall Street, but when it came to their own money, they invested in T-bills.

The second cliche you hear a lot of is that you make money by being smart. I’ve met a lot of people who made a lot of money, but almost none of them made it by being truly intelligent. Most made it by being shameless in some fashion: by kissing their bosses' behinds, by backstabbing their coworkers, by lying to their customers, by luck, or by outright thievery. Most of these professionals had no clue which stocks (or bonds) were going up (or down), though this certainly didn't prevent them from having very vocal opinions on these matters.

The third cliche is that as soon as somebody makes a certain amount of money, he is going to get out of the business and pursue his real passions. Yet nobody ever seems to retire. It's partly because some people can't seem to save money. (A typical Wall Streeter who has made, say, half a million dollars for ten years, might have a net worth of only two or three hundred thousand dollars, thanks to wild spending habits, poor investing, and perhaps a divorce or two.) The other reason is that the amount that they deem sufficient to retire on just keeps growing. (J.P. Morgan was once asked how much money is enough for a man, and he replied, "Just a little bit more." He may have been referring to himself, but his answer applies equally well to ninety-nine percent of the people who work on the Street.)

The fourth cliche has to do with "family values." Most guys pay lip service to the idea of spending time with their families, and like to imply what wonderful fathers they are. But in fact, a large percentage of them -- usually the ones who broadcast their "family values" the loudest -- actually go out drinking most nights, and spend a good part of their weekends playing golf with their buddies.

George never uttered any of those cliches. Yet he actually risked his own money. He got rich by being right (and by seeing who was wrong, in the case of his shorts). He stopped working for someone else at a point when he had what was by Wall Street standards a respectable, but by no means princely, bank account. And he did all this while spending lots of time with his children. (George also visited his mother regularly. Before she died in August 2004, he drove from Brooklyn to D.C. to visit her once every ten days or so.)

George's hot streak has extended beyond 2001 (though he no longer bets the family homestead). He sits on several corporate boards, is on the Visiting Scholars Committee at Harvard, and the board of Shakespeare in the Park. Yet at 52, he still looks young and spry enough so that when older white ladies see him coming in their direction on a city street, they clutch their pocketbooks just a little tighter, completely unaware of the irony. (In the summer of 2004, and again in the spring of 2009, George was part of a world record-setting Masters relay in track.)

When I try to convey a sense of George to people, I don’t have time to say all the things I’ve said here. So sometimes I summarize by saying, “He’s not the handsomest guy I’ve ever known, or the smartest, or the toughest, or the richest, or the funniest, or the best all around athlete. But he’s so close to the top in every single one of those categories that I have to say he’s the hottest shit guy I’ve ever met.” (People who haven’t met him generally nod politely, people who have usually nod with more enthusiasm.) Another reaction I often get when describing this essay to another guy is resentment that I haven’t considered that other guy for the title. (Sorry, you don’t come close.)

Old age may be lurking, but George is still the coolest guy I know: when his eyes light up with that mischevious glint, the world always seems a more appealing place.


Update, July 2009: Has moved to DC. No longer quite as rich, and the sports car has been replaced by a Lexus. But just as cool as ever (just saw him this week).