Commentary Magazine

Coming of Age in Chicago

I have always doubted that Chicago ever even faintly resembled the city of Carl Sandburg's poem, but I know for certain that by the time I was born there the city of the big shoulders had developed a serious slouch. The year was 1937, the event took place on the West Side. The neighborhood of my birth is the same one described in Meyer Levin's novel, The Old Bunch. The old bunch has long since departed, and Negroes live there now. Today the place is a jungle into which, even in a car, one enters with trepidation and from which one exits with relief. Apparently it was at best never much more than a good place to flee from. Flee my family did, as part of a general Jewish migration across Chicago to the far North Side and thence, later, into the northern suburbs. This particular migration was conducted in moderately high style, topping, surely, our family's previous migrations: my grandfather's from Russia to Montreal to avoid conscription into the Czar's army; my father's from Montreal to Chicago at the age of seventeen, because if you were a smart Jewish kid in Canada even mildly on the make, you sensed that the United States was where the action—which is to say, the money—was. On our way to Chicago's North Side, I recall living briefly in a reasonably fashionable apartment hotel, then in an apartment on Sheridan Road off Lake Michigan, and then finally settling into a neighborhood called West Rogers Park. At the time, the West in West Rogers Park was no mere geographical distinction, for it denoted a full notch up on the status gauge over plain Rogers Park. It was in West Rogers Park, in a predominantly Jewish, wholly middle-class atmosphere that I grew up—without want, without fear, without, as we used to say around the neighborhood, sweat.

My friends and I were the sons of survivors, successes, in a modest sense of the word, even winners. Our fathers owned small businesses, were doctors or dentists, or shrewd, knowing lawyers. My own father began as a salesman. Too old for World War II, he stayed in Chicago during the war and made a bundle. A realist, he will tell you even now that you had to be very bad not to do well during those years. On one occasion, in less than an hour's time, a single sale brought him a $10,000 commission. He did so well, in fact, that the people he worked for couldn't stand it and attempted to cut his commissions. So not long after the war he left the firm and went into business for himself. It was shortly after this that we moved to West Rogers Park. As a child I remember that whenever I asked about our financial situation I was told that we were not wealthy but “comfortably off.”

This was typical. In all financial and social matters a conservative, my father played his cards not so much close to his chest as inside his shirt. During a stretch in the middle and late 50's, he began driving Cadillacs. He did so largely for business reasons. His customers were impressed with the outward signs of success, and if it helped business, he was ready to supply these signs. But he was always a bit uncomfortable about the ostentation of a Cadillac, and every night, returning from work, he would hide it in the garage. He had a partner in those years, a swinger who bought his clothes in New York—a dozen pair of shoes at a whack!—and who, in addition to driving a Cadillac himself, also kept a red Corvette convertible and wore a carefully manicured goatee. In later years, my father bought him out; and soon after, with obvious relief, he dropped the Cadillac and began driving an Oldsmobile.

We belonged to none of the town or country clubs open to Jews in Chicago, though the parents of a great many of my friends did. Insofar as I could see then, or can now, these clubs all operated on wholly plutocratic principles: if you had the cash, could pay your tab, were not too clearly involved with the Syndicate (though at some clubs this didn't hurt at all), and were a sufficient number of years removed from the West Side, membership was yours. The number-one subject in these clubs was money. Money, indeed, was the meaning of Chicago, what the city was all about. Unlike the East, Chicago's pretensions to an aristocracy or social elite were nonexistent. The city's long-established families, the Armours, the Swifts, the Wilsons, were, quite literally, butchers. Everywhere in the city money was the sole, the whole, measure of the man.

Often I was taken by a friend as a guest to one or another of these clubs. The Town Club, which then occupied the top floors of the Sheraton Hotel, in whose card-rooms men played gin, Hollywood-Oklahoma, for a dollar a point, games in which, without any trouble at all, on a bad night one could drop five or ten grand. The Covenant Club, where the big attraction was the food and the shvitz. Green Acres, the country club in Northbrook, in whose locker-room I can still recall four men, bald and fat and hairy-backed, swathed in towels, smoking cigars, nibbling at immense slices of blood-red watermelon, and playing gin, while elsewhere in the room Filipinos in white shirts and black trousers with a gold stripe down the sides hustled about shining members' shoes, arranging lockers, and greeting members freshly emergent from the showers with great puffy blue towels. Two other clubs—the Standard Club downtown and the country club in Lincolnwood, known as Bryn Mawr—were both then said to be controlled by German Jews and I had no connections in either.

My father would not have allowed himself to be caught dead in such clubs. I never found them anything but fascinating. Later I came to find certain virtues in my father's conservative style, but in my teen-age years it was the wheelers, the hustlers, the smart-money types, who made the strongest impression on me. The father of a friend of mine, for example, who was supposed to have bet $100,000 on a mid-week baseball game. He had to have been a very high roller to get the bookies to take on that kind of action, but in any event one drizzly Tuesday afternoon (as I have always imagined it), feeling lucky, or impatient, or bored with small victories, he called his book, placed the bet—and lost. A complicating factor was that he didn't have the money to pay off. Normally, this would entitle a man to a bullet in the head, his dead body stuffed into the trunk of an old car which, about two weeks later, would be discovered in the parking lot of some quiet neighborhood Lutheran church. However, it was in the middle of World War II and, as the story goes, the word had gone out not to make any hits on men in uniform. So my friend's father did the only sensible thing to do under the circumstances: he joined the Navy. In Navy bell-bottoms he walked into the office of the men to whom he owed the hundred grand. With a confident smile, he is supposed to have said: “I just dropped by to see if my debt to you gentlemen can't be negotiated.” Here was a man I admired.

Yet one could be a certified Chicago hustler on a much smaller scale. Big time or small, it seemed almost everyone I knew or heard about in Chicago in those days was on the make, in on the take, with the show, dedicated not to be done in, to be—to put it flat out—the screwer rather than the screwed. There were cab drivers half of whose income derived from taking passengers to hookers' apartments; lawyers who founded whole careers on whiplash and other fake injury cases; doctors and dentists for whom medicine was strictly a sideline and whose prime interest was real estate; bailiffs, driver's-license-, elevator-, restaurant-, building-, and health-inspectors who tripled and quadrupled their regular salary through handouts, bribes, and other assorted shmeers; cops who specialized in making out and signing phoney robbery insurance claims, fixed traffic tickets, collected personal and business debts in uniform, or, as happened in one noteworthy instance, actually burglarized homes.


To a certain extent this went on in other American cities. But in Chicago it went on to a very great extent, and in fact most of the people I knew took a fierce kind of pride in the city's corruption. It was the badge of our sophistication, and we wore it early. As soon as I acquired my driver's license—I was fifteen at the time—a friend taught me to insert a five-dollar bill between it and the wallet-window in which I kept it; this way when a cop stopped me for a traffic violation and asked to see my license, the bribe would be at the ready. Watching the smiling, red-faced Irish cop slip the bill out of my wallet after stopping me for running a red light was a distinct thrill. Smooth! Along with the fin, an air of perfect understanding passed between us. It was a rite of passage successfully brought off, a true Chicago Bar Mitzvah.

Not so much behind everything in Chicago but towering above it was the Syndicate. Or rather the idea of the Syndicate. Nobody really knew anything specific about it, yet nobody really doubted its existence. In Chicago the “Outfit” or the “Mob,” as people who liked to be thought very hip sometimes called the Syndicate, seemed quite different from what it has since been revealed to be in such places as New Jersey. From a distance, at any rate, it seemed no cozy Cosa Nostra, no hierarchically-arranged network of small-business-minded hoods, but a crunching corporation—smoothly and efficiently run, if still a little rough round the edges. Nor was it so exclusively Italian as it appeared to be in the East. In Chicago, Jews were heavily involved, mostly in administrative jobs, such as bookies or lawyers or fight promoters. West Rogers Park had its own Benya Kriks, men with names like Acey Feinman, Potsey Pearlstein, Hawkface Bernie Greenburg. Rumors were nagging, unverifiable, and delicious. I went with a girl in my junior year in high school, for example, whose father never worked. From the beginning of spring to the end of fall, he golfed. Winters he played gin at the Town Club. His brother, it was firmly established, had been a Capone lieutenant in the 20's. It was said that, as a legacy from those days, he, the younger brother, still collected a dollar a month on every juke box in the city of Chicago.


When I look back on it now, it all seems a bit like bad Damon Runyan, but it was very rich stuff at the time. The entire set-up was one I felt wonderfully comfortable in. Its guiding philosophy was “let Paris be gay,” and its rules were uncommonly simple: go easy; don't make waves; why fight City Hall when for less than you might think you may be able to buy it?—and at all times and in all ways take particular care to distinguish yourself from the Polacks, the marks, the rubes, and the general lot of losers. In Chicago there were finally only two classes: winners and losers.

Self-regard had a lot to do with determining which of the two classes one fell into. The Fat Man was a case in point, a loser by most standards but his own and therefore not a loser at all. “Kid,” the Fat Man once said to me, “who's got it better than me? Not many guys, that's for sure. I like my job, I eat good, I see all the movies I want, and I get it on the average of three times a week—plus once at home.” That may not have been a true champion talking, but the man has to be counted a contender.

Fred Moscowitz, the Fat Man, made collections for my friend Philley Goldman's father's finance company. I first met him when I was sixteen, and for years afterward I thought of him as the first adult to take us seriously, to treat us, at a time when such treatment was terribly important, as grown-ups.

In order to lend his father a hand and, while at it, to learn the business, Philley Goldman began working on Saturdays with the Fat Man sometime during our sophomore year in high school. Philley brought great stories back from these Saturday outings. The Fat Man was a riot of good humor, a mine of information, a superior guide through certain inner chambers of the city. He took Philley to special restaurants (cheap but good), placed small bets for him through his various bookies, accompanied him to inexpensive hookers, and put him on to others whom he himself had visited during the week and who had some specialty he thought Philley might get a kick out of. Sometimes Philley and I would follow up on these tips. (Once Philley telephoned the Fat Man to thank him for a number which proved very satisfactory. “Hi Fred,” Philley said, “just calling to thank you for that Doris number. Terrific! Really great! Everything you said she was, and more.” A gravelly voice at the other end responded: “This is Mrs. Moscowitz.”)

Philley finally arranged for me to accompany him and the Fat Man on their rounds one Saturday. It was just after seven o'clock in the morning when the Fat Man drove up to Philley's house in the company car, a powder-blue, 1950 Plymouth station wagon. He was bald, ruddy, had a warm rasp to his voice (a milder version of the late Andy Devine's), stood about 5' 10″ and weighed in at somewhere over 300 pounds. His skull apart, he seemed not to have a bone in his body. His specialized knowledge of the best cheap restaurants in Chicago had taken its toll, and one had only to see him eat once to realize that his tremendous heft was in no way connected with glandular trouble. In the driver's seat of the Plymouth he draped a bib-like rag—his shmatte, he called it—over the great hump of his stomach to prevent the rubbing of the steering wheel from wearing out his pants.

After Philley introduced us, I addressed him as Mr. Moscowitz, but he immediately told me to cut out that “Mr. Moscowitz crap” and call him Fred. So as not in any way to make me feel the outsider, he insisted we all three sit up front; and so we did, with Philley crammed in the middle and I wedged flush against the door. The Fat Man was the kind of driver who was so good you didn't particularly notice he was even at the wheel. When a car behind us honked and passed us on the left, however, he rolled down the window in time to yell at the passing driver, “Blow it out your duffelbag, farthead!” Heading toward the city's South Side for the first collections, the Fat Man provided a tour of Chicago's great whorehouses. On Lake Shore Drive he pointed out one in an expensive high-rise which, according to him, had been one of the city's glories in the 30's. “Three bucks a trick is all it was,” he said, “and they served cocktails. Lovely girls, too. Break their little hearts if you didn't dance with them a time or two beforehand.”

In the back of the Plymouth the Fat Man kept a few old sheets, a blanket, and some loose rope. These were there in case he had to repossess some item on which the payments were hopelessly behind. Mr. Goldman had gone into the finance business only a few years before, and most of his business still came from furniture stores in slum neighborhoods—“risky paper,” it was called in the trade, but not at all unusual for a small company just starting out. Philley had told me earlier that a repossession was to be avoided at all costs, the reason being that the repossessed item usually turned out to be worthless. When a man saw that he couldn't keep up payments on his television set, or refrigerator, or bedroom suite, and was therefore going to lose it along with all the money he had thus far paid in on it, he almost invariably entered his own little criticism of the system by demolishing whatever it was that was about to be taken away. (The logic of this still seems to me impeccable.) So if you were in the finance business, you threatened, you cajoled, you negotiated, you allowed for every kind of slackness, you stood ready to be called Jew-bastard (whether, I suppose, you were in fact Jewish or not)—and despite all this, in many cases in the end someone like the Fat Man would have to drag the sheets, blanket, and rope out of the back of his car and haul a television console with a smashed picture window and cigarette burns all over the cabinet down three flights of stairs. Not a very clean business, but profits were high.

The plan for the day was to begin on the South Side, making the first collections in Negro neighborhoods, then working our way back north. For the most part, the collections were fairly routine. The buildings in which we made them were almost uniformly dilapidated, with only minor variations in decay. In one the mail boxes swung loose, sprung from their hinges. In a number of others not very witty graffiti—“Henrys Mother Sucks”—adorned the walls. Stairway carpets, where they existed, were threadbare. Hallways stank of urine, vomit, cooking odors. Behind doors dogs barked, men and women argued, babies cried. An occasional apartment still had a mezuzah nailed to its door-jamb, the remnant of previous occupants in these hand-me-down buildings.

The Fat Man knocked on the doors of his accounts with meaty authority. Our first call brought a young mulatto woman to the door in her nightgown, a child at her breast. A few calls later a large black man who looked to be in his mid-thirties shoved a five-dollar bill into the Fat Man's hand and, without a word or a look at any of our faces, slammed the door. Later in the morning an elderly woman who didn't have that week's payment came on overly friendly, asking, with what she must have thought was great con, if we'd care to come in for a bite of breakfast. Some of the Fat Man's accounts had their payments when they came to the door, some went back into their apartments to get the money, some didn't have their payments but assured the Fat Man they would get some money to him the following week, and some didn't have the payment and chose to make no excuses about it. The Fat Man, meanwhile, gave pretty much what he got: he returned friendliness with friendliness, con with con, surliness with surliness. After each call he made a check mark on a 5″x 7″pink card.

Since it took a lot out of the Fat Man to climb so many stairs, that morning Philley and I handled the accounts who lived in third-floor apartments, leaving the Fat Man to wait in the car. In one apartment five Negro men were sitting around watching a baseball game on a television set for which we had come to collect a payment. The account, a flat-featured, very black man in his forties named Leroy Green, had missed his last two payments and he now informed Philley that he didn't have a payment this week either. He said so without any apparent anger or anxiety; in fact, he never really took his eyes off the ball game. Nor did the other men in the room look away from the game.

“Hell, Mr. Green,” Philley said, “that's OK. Frankly, just between the two of us, I personally don't give a damn if you ever pay another penny on that set. My problem, though, is that I've got that prick of a boss on my back. That's a mean son-of-a-bitch, man, you better believe it.”

I thought of Mr. Goldman, a tall, slightly stooped man, very gentle in manner, who had a sly sense of humor and extremely kindly eyes.

“When I get back to the office today,” Philley continued, “I know exactly what he's going to say. He's going to tell me, screw that Leroy Green. He misses one more payment, you pull the television set out of his apartment. Let him stare at the walls.”

Green seemed unmoved, a little bored even. He wanted only to get back to his friends and the game. I vaguely wondered what restrained this roomful of black men from pitching the two of us out of the window. Green finally mumbled something about trying to have next week's payment; and as we were leaving, Philley, putting on the finishing touch, remarked on the high quality of the television set's reception, comparing it favorably with his own, a last indirect reminder of what a shame it would be to have it repossessed.


We had lunch that day at a restaurant on the West Side called Little Jack's. Chopped liver, chicken soup with kreplach, rolls and rye bread and pickles and sour tomatoes. Philley and I each ordered a corned-beef sandwich, but the Fat Man told the waitress to make it two sandwiches each and better add a side of fries. For himself, he ate everything we did, only more; instead of the corned beef he had an entire flounder served with a small mountain of mixed vegetables and flanked by two baked potatoes. The house specialty at Little Jack's was cheese cake. After we had crammed down a huge wedge, the Fat Man asked, “How's about a second hunk, boys?” He was clearly disappointed when Philley and I each said no, we couldn't handle another piece. “Never know when you'll be back this way again,” he said. “Fact is, you owe it to yourself to have a second piece,” and then to keep his own books clear he ordered another for himself, which he washed down with his third bottle of soda.

After lunch the Fat Man parked the Plymouth in front of a one-storey frame house on Carroll Avenue, the only residence on a block otherwise made up of small factories. He banged on the door, which at first opened only partially, held back by a chain lock. “Why, it's the fat boy himself,” said a small yellowish woman in an apron, wrinkled and in her fifties, who stood in the doorway. “How you making it, tons of fun?”

“Just barely, Gert, just barely,” the Fat Man said.

Philley and I followed him inside, past a small foyer into a cluttered room. The room had, among other things, a lunch counter and six rather beat-up high stools. Behind the counter was a double hot-plate and a shelf stocked with seven or eight cans of Campbell soups and a few packages of breakfast cereals. A menu listing three or four sandwiches along with a meat-loaf plate was scribbled on a cracked blackboard resting on the shelf. A man in a pair of Army surplus coveralls sat at the counter drinking a cup of coffee and watching cartoons on an old television set perched on a stand high in a corner behind the counter; he probably worked at one of the factories in the neighborhood.

“Can I fix you boys something to eat?” Gert asked.

“To tell the truth, Gert,” the Fat Man said, “the boys here are a little more interested in what you got in the back.”

The man at the counter was leaving, and Gert excused herself to take his money. After paying, he said: “Say, Gert, can you take care of this for me?” He slipped a traffic ticket out of his wallet.

“Sure can, honey. No big deal.” Gert took the ticket, unfolded it, and put it in a cigar box with a number of others. “My man comes in to pick these up on Monday. Whatever it comes to, you pay me later.” She followed the man to the door and locked it behind him.

“Now,” she said, speaking to the Fat Man, “I believe you said something about these boys' interest in what's out back. How's about yourself today, fatso?”

“Shit, Gert,” the Fat Man said, “you know I make it a rule never to pay for it.” They both laughed.

In the next room two women in housedresses sat on a couch whose stuffing was coming out of the arms and back. One woman was short, on the chubby side, and light skinned. The other, who was filing her nails, was large and very dark. Neither was young or attractive. Philley left with the shorter woman, and I followed the other one into a small room off to the right. After we had settled on price and she had checked me for disease, she slipped off her housedress and eased herself onto the bed. I had just removed my windbreaker and kicked off my shoes when she said: “No need to take off that sweater or your socks, sugar.” The whole business was over with very quickly.


Prostitutes were nothing new to us. My own first venture was at fifteen, which set no records for precocity. The woman's name was Leona. She was a truly striking mulatto, what the sporting crowd in those days called a high yellow, the ex-wife of a fighter who, for a few brief moments in his life, was light-heavyweight champ of the world and who, while still not yet forty, was stabbed to death in the Sutherland Lounge on Chicago's South Side. The walls of Leona's apartment were painted black and Chinese red; the ceiling of her bedroom was mirrored. Professionally she executed a stunt called “around the world,” which, combined with her good looks, brought her in a brisk business. She drove around the South Side in a new maroon Lincoln convertible. In her bathroom a burnt spoon, a needle, and a syringe lay on a shelf above the toilet.

The lush air of corruption surrounding women like Leona was always at least as enticing as the sex, which in fact tended to be quick and, to put it mildly, perfunctory. (“Wham, bam, thank you ma'am”—an old Chicago whoremonger's expression.) In running off to hookers as early as we did we sought, certainly at least as much as any kind of sexual relief, emulation. Whom were we emulating? Not our fathers, not any one person, not even any particular group of people, but rather what we loosely though confidently took to be a Chicago style of manhood. To go to hookers, to have a bookie, to know someone with proven Syndicate connections—this was to partake of the finest Chicago had to offer.

There was also the sheer fun of it. Trips of fifty or sixty miles to the cathouses of Braidwood or Kankakee, Illinois, were for us great communal events, and we went off on them the way I suppose other high-school kids went off to a state high-school basketball tournament. Five or six of us would pile into one of our father's cars for the big drive out. On the way we would laugh, sing, tease any novice who might be along—“Whatever you do, Danny, don't let her get her legs outside of yours”—and on the way back lie a little about the action with the girls, who usually had names like Rusty, or Bobby, or Pam. The highlight of these trips came on the drive back. On a turn on the Outer Drive we passed a large neon sign—since taken down—which blinked, “Dad's Old-Fashioned Root Beer, Have You Had It Lately.” A very big laugh line, this.

It was on one of these trips that I first got to know Jeremy Levy. He was a year and a half older than I, an excellent athlete with an enviable reputation as a gambler as well as a number of unusual sexual adventures to his credit. One of the stories about Jeremy was set in Miami Beach. While down there on vacation, this story went, an uncle and three of his uncle's friends offered Jeremy a hundred dollars apiece if he would throw himself in with two lesbians who were performing for private parties in a suite at the Saxony Hotel. Jeremy collected the money. When I got to know him better, I never asked him to authenticate the story. Yet I found no reason to doubt its truth.

Jeremy's father was a millionaire. He had made his money over a very few years in the home-improvements business—a hustler's operation, borax all the way. It was a business so lucrative that many of his salesmen were making (this was in the middle 50's) a thousand or twelve hundred dollars a week. Jeremy's father, a sport, would fly back and forth between two distant cities to attend all the games of the World Series. It was not at all unusual for him to bet ten grand on a welterweight fight in, say, Philadelphia, fly out to watch it, and return to Chicago that same night. He kept odd hours, and I never saw very much of him, but you didn't have to to know that he was a man with no small talk. He was lean and tall, bald, with a thin mustache, a hooked nose, and dark, cheerless eyes. Possibly putting a knife in someone's back could bring a change of expression to his face, but not much less.

Jeremy looked more like his mother. He was small (around 5'5″), almost dainty, fair, though with dark hair, and had clean straight features inclining slightly toward the delicate. Like his mother, he was good-looking in a soft, toned-down way. With his mother's manner and looks and his father's mind and heart, Jeremy was doubly dangerous. In the murky waters of Chicago corruption, he swam effortlessly. He was the only person I've ever seen who looked absolutely at home in a whorehouse. Through his father's connections, he had tickets to everything: Bear games, Cub games, Blackhawk games, all fights, musical comedies, a box at both tracks, memberships in both a town and a country club, free rein with charge accounts at stores and restaurants. His cash was unlimited. On one particular afternoon I saw him blow $400 at Arlington Race Track and then return that night to the trotters at Maywood and win $600. He had of course his own car—a green Chevy, the current year's model, one of the first of the hard-top convertibles. Yet with all that his parents gave him, it never occurred to me to think of Jeremy as in any way spoiled, or as the son of a rich man. The reason was that I was sure that even if his parents had nothing to give him, Jeremy would still have gotten whatever he wanted. He was too intelligent, too single-minded in his desires, to be denied. In this world he was a guest, a taker, a winner born and bred, with a quiet though abiding love of putting it to his fellow man.


Jeremy's friendship with me, at least at its beginning, involved the purest calculation on his part. Not long before he had taken up with me, he began dating a girl in my year at school named Sharon Levenson. For somewhat cloudy reasons, Sharon was one of the most popular girls in the school. The reasons were cloudy because she was not particularly good-looking—she was, in fact, rather plain, too fair, without memorable features, or much of a body. Nor was she at all clever. But there was about her a certain vulnerability, a quality of fragility, that evidently made all males want to protect her. My own feeling toward her at any rate was protective, and I recall feeling not at all good about learning that she was going out with Jeremy Levy.

Yet it was in connection with Sharon that Jeremy enlisted my friendship. With all his other action, Jeremy had not expended much effort on girls, certainly not on girls of Sharon Levenson's kind, and now that he had started dating Sharon he was setting up a full-court press to win over her and her entire family. My place in this campaign was to be fixed up with Sharon's younger sister, Roberta, who, Jeremy told me, had a crush on me. Not only did he arrange a date between Roberta and me, but he saw to it that on this first date he and Sharon doubled with us. His style with Sharon that evening was husbandly, with her sister and me almost fatherly. We saw Sarah Vaughan on stage at the Chicago Theater and afterward ate at Miller's Steak House in West Rogers Park, where Jeremy signed for the bill. We dropped the girls off at about one o'clock, and then took off to a poker game already in progess on Lake Shore Drive.

A word here on our attitude toward girls. Girls for us were of two kinds, nice and not-nice, and in either instance certainly never of primary importance. The not-nice girls you tried to lay with as little fuss and as much promptitude as possible. The nice girls, as a local hustler once remarked to me, you had to be a genius to lay. Besides, our criterion for a nice girl was not merely that she be sexually almost unapproachable, but that, should she be approachable, she should be sexually awkward. I remember a friend of those years once describing in fairly intricate detail what seemed to him a scene of special horror. It went something like this: it is your wedding night, and you are about to consummate your marriage to a girl you had all along thought good and pure and sweet and innocent. You kiss, she says oh darling, then disappears under the sheets to perpetrate something Byzantine on you. There it was: one's wife ought in all decency to be neither good at nor remotely interested in sex. Sex and the kind of girls one thought of marrying were separate subjects. Grand little mobster that I was, I once joined three friends at the apartment of a hillbilly hooker on the Near North Side before taking a “nice” girl to a dance.

Jeremy thought along the same lines as the rest of us on this subject. It would be making him out a harder number than he was to say that he planned his relationship with Sharon to turn out as it did. At the outset, I think he cared a great deal about her, and cared even more about the idea of her being his girl. Perhaps his campaign to win her over succeeded beyond his own expectations, for before long he took me into his confidence by telling me that he and Sharon had begun to sleep together. I felt no envy, no jealousy at this piece of news, but I would be lying if I said it didn't somehow pain me. And apparently Jeremy himself felt at first somewhat queasy about the whole business. He told me later that he went to his uncle, his father's younger brother, to ask his advice about it. The advice he got was that if he didn't screw this broad someone else would. The queasiness disappeared.

In its place appeared a firm determination to get the most out of what he had. Jeremy now played at being the husband with even greater intensity. He was always leaving Sharon his car. During the week he would take her out to the track, to the fights, to ballgames. Weekends there were musicals, nightclubs, movies. Sundays, while his parents were at their country club, he and Sharon spent all day at his house. A very different tone entered his accounts of their sexual adventures. Where earlier he seemed to be telling me what they had done together in order to signify her love for him, now his stories were told with a fiercely cynical pride, such as one of his father's salesmen might adopt to tell how he had sold screens and awnings to a family of Eskimos. I suspect I must not have been sufficiently enthusiastic about these tales of conquest, because now Jeremy began telling them to me with a certain persistence, filling me in on more details than I cared to hear. The more he told me the more Sharon was irrevocably, irretrievably, soiled. Jeremy now regarded her with the easy contempt with which in Chicago any loser is regarded. Perhaps she had been a disappointment to him. Sweet, pure, innocent Sharon—she was Jeremy's final proof that all the world was, if not corrupt, corruptible.


Not quite final, though, for Jeremy evidently felt this particular theorem still needed notarizing and, though I did not yet know it, I had been chosen to serve as notary public. We were watching a baseball game one Saturday afternoon on television in his parents' richly finished basement, when Jeremy suggested that I stay for dinner and after that watch Sharon and him make love. It would be very simple, as he saw it, practically no chance of being caught. I would wait in a closet behind the bar in the basement; he would bring Sharon down, ostensibly to watch television, though of course to do what they always wound up doing. Once they had gotten down to business, I could slip out of the closet to station myself behind the bar, from where, in a crouching position, I could watch the whole thing.

Jeremy began emptying out the closet to make room for me. I would of course have to be very quiet, he said, pitching out galoshes, raincoats, and odd sports equipment. He had clearly been planning this escapade for some time. I was not especially shocked or disgusted by what he proposed; the voyeur in me was even slightly attracted. But I decided finally to refuse to go along because I somehow sensed that my position in that closet would be much more compromising than Sharon's beneath Jeremy on the basement couch. When I told Jeremy I had other plans for the evening that I really couldn't get out of, he was very obviously hurt.

In the fall Jeremy went away to the University of Wisconsin. He called me when he came home for Thanksgiving holidays and I saw him once during Christmas vacation, but before the year was out we had lost touch. In later years I would sometimes see him at a basketball game at Chicago Stadium or at the Amphitheater, but we no longer had much to say to each other. Every so often a friend would report that he had seen him. His father had in the meantime become involved in a scandal that held the front pages of the Chicago papers for better than a week. He was called before a number of Senate subcommittees, and at one point was sought simultaneously by both the FBI and the Syndicate. The scandal had broken Mr. Levy, and the last I heard he had lost his business and was reduced to managing an apartment building on Sheridan Road. The official line on Jeremy was that he was selling insurance. Then one day in a middle-of-the-paper story in the Chicago Sun-Times, one of those stories to which in Chicago there is invariably no follow-up, I read about a raid on a North Side bookie joint whose weekly handle was estimated at seventy-five grand. The police and for good measure the FBI were looking for the three men who ran it, one of whom was identified in the story as Jeremy Levy. About six weeks later a friend of mine, out for the day with his daughter at Lincoln Park Zoo, bumped into Jeremy, who was there with his young son. He was looking very well, my friend said, and claimed to be finally gaining a foothold in the insurance business. I find I don't spend much time worrying about his getting on in the world.

Yet I shall always be grateful to Jeremy, as I shall be to growing up in Chicago, for teaching me many valuable things and, valuably, teaching them to me early on. Because of Chicago, that is, certain kinds of knowledge came early: that men are attracted to power in all its forms and much less respectful of its uses than of its attainment; that with only the slightest encouragement men are ready to give vent to extraordinary viciousness; that, finally, there is nothing very original about sin. These conclusions, so startling to others when they stumble upon them in their maturity, are the A-B-C's of growing up in Chicago. Indeed, if one is immersed deeply enough in the life of the city they are likely to seem the whole alphabet. But if, with a bit of luck, one is able to rise a few inches above Chicago without losing sight of its lessons, then what a different look the world takes on: how special goodness seems and how exhilarating to come upon a simple act of decency!

About the Author

Joseph Epstein is a regular contributor to COMMENTARY.

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