The Jimmy Winkfield Stakes



A racetrack in obsolescence.


Photo: Ilya Lipkin

Every year on the third Monday of January, the Aqueduct Racetrack, in South Ozone Park, Queens, runs a six-furlong race in honor of Jimmy Winkfield. The choice of date, Martin Luther King Day, is not accidental. Of Winkfield’s many accomplishments, which include winning the Russian Oaks an incredible five times for Czar Nicholas II, he is best known as the last black jockey to run a winner in the Kentucky Derby, in 1902.

To be black in the world of horse racing was no easy thing in the early part of the twentieth century. Winkfield, born in Kentucky, had enjoyed a storied career in Russia and France, but when he returned to America he was forced to enter a reception held in his honor through the hotel’s service entrance, with the bellhops and the kitchen staff.

Because of the raw January weather, attendance at the Jimmy Winkfield Stakes is usually rather sparse compared to the bigger events at the height of the racing season. This year, my older brother Ilya and I saw the race completely on a whim—we thought it might be fun to trek out to the Aqueduct like we used to when we were younger. Back then, if the weather was fine, our father would drive us to the track out in Ozone Park, a favorite destination for the unattached men in the neighborhood. Edik from the dry cleaners down the street was a fixture there, as was Pavel, the bartender at the Pennant Sports Bar on Northern, and Parsons, whose brother was an orderly at the elder-care facility where our grandfather died. To me, gaining admission to that world of working men was no less exciting than the races themselves. I watched with great interest as they quaffed beer and studied the odds on the board and cursed when they invariably lost their money. Being a bit older, Ilya had a better sense of what was actually going on. He nagged Pavel until the bartender showed him how to decipher the near-hieroglyphic racing form. The one time my father let him place a bet, we won eighty dollars. It proved to be a red-letter day, because that same afternoon, I fed a carrot to Cigar, the Hall of Fame thoroughbred, just before the first big win of his career. (The Aqueduct now runs a race in his honor as well.)

In the years since, we knew from the Post, Internet gambling had decimated the Aqueduct’s attendance numbers, and, fed up with the corruption and mismanagement of the New York Racing Association, politicians of both parties had promised to close it down. Still, I was chagrined to find the track’s once bustling lobby, which had always been the most thrilling place, completely empty except for a few gamblers who had arrived early to claim their carrels. Twenty years ago, Champs, the track bar, would have already been packed—my father always complained about having to wait thirty minutes for a glass of Old Milwaukee. Now the stools at the imitation brass rail stood patronless. Everywhere we went, we encountered an eerie silence. The nattering of the girls at the betting window and the swish of the janitor’s cloth as it passed over a plaster jockey were completely swallowed by the cavernous ceiling and cement walls. No effort had been made to update the decor or to effect even the most minor of repairs. The only thing that had not been there during our last visit was a red-and-blue sign painted onto the concrete that read UPDATE YOUR STATUS. Ilya waited with his camera until a gnarled man with a bulbous red nose passed underneath it before snapping a photo.

What little remained of the grandeur we recalled was most in evidence outside, on the building’s track side. There, a dozen or so spectators were watching one of the grooms walk a horse through the sandy loam, his flanks covered with a heavy tartan blanket against the cold. The sheer scale of the structure behind us, with its rows and rows of seats soaring up to a huge winged roof, lent dignity not only to the horses lining up for the first race but to the score or so of late-arriving men who began to trickle into the stands once the call to post rang out over the PA. It was hard not to be struck by the variety of faces filling up the seats. There were a few blue-eyed, straw-haired men who came, judging from their accents, from the drizzly lowlands of Northern Europe. Next to Ilya, a five-man delegation from the mountains of Peru was arguing heatedly over the odds printed in the racing form. Up by the rail, two Asian men in baggy denim and worn-out flannel passed a pair of binoculars back and forth. Anywhere except the Aqueduct these men would have cut a sorry figure; here, away from the judging of eyes of wives and children and police officers and family-court judges, they could at last lay claim to a measure of respect. Not only were they valued customers, they were experts, and with a bit of luck, they could be rich as well—a little rich, at any rate, if only for the afternoon.

* * *

The first race, six furlongs along the inner dirt track, was brief and unassuming. Starting near a copse of leafless trees at the far end of the track, the riders pulled toward the rail as they came around the bend, fanning back out as they came down the stretch. The silence in the stands was broken by a chorus of shouts—“Four! Four, five!”—directed at the high-definition monitor tracking the horses’ progress. When the dust had settled—figuratively speaking, since a light drizzle had turned the loam to muck—a dark brown colt called Green Gratto had taken first place, knocking the 3-1 favorite, Team Lazarus, out of the money. Some of the less fortunate gamblers elected to abuse themselves by watching Green Gratto and his owner have their picture taken by the boxes of chrysanthemums in the winner’s circle. Most of the crowd, however, quickly shook off the disappointment and filed back into the building to see the simulcast race at Sam Houston Park, leaving behind a small flurry of torn betting slips for the gulls to pick through. The scrawniest and most desperate of these animals tried to choke down loose bits of losing tickets. They began to take on the glum aspect of the men that had discarded them.

Inside, Ilya and I were joined by our long-time friend Chris Cumming. Like us, Chris had found himself drawn to the track over the years; in junior high, he and his father often went not only to the Aqueduct but also to Saratoga, up I-95. As a graduate student at UCLA, Chris observed the start and end of each semester by driving out to Santa Anita Park—with its expansive view of the San Gabriel Mountains, widely considered the most beautiful racetrack in the world. Chris made no pretense of being an expert when it came to horses, but I respected his opinion implicitly, so I asked him, once we had picked out two seats right by the finish line for the second race, whether it was possible to make real money at the track.

There were two prevailing opinions, he said. The first was that the races at every track—Aqueduct, Sam Houston, Santa Anita, Saratoga, whichever—were massively rigged. It was an outlook born of ressentiment, but it was confirmed by the testimony of dozens of jockeys, trainers, and organized criminals. (In the book Wiseguy, for example, the infamous gangster Henry Hill brags that he and his associates rigged so many races at the Aqueduct that the NYRA was forced to discontinue the Superfecta bet they had been using to maximize their profits.) The best that one could hope for then was that one’s interests did not run counter to the interests of whoever it was that controlled the outcome of each race—a pretty bleak hope, on the whole.

On the other hand, from what Chris had heard at Santa Anita, it was just as widely held that horses were nothing more than dice with legs, and that for all the information offered in the racing form—the horse’s parentage; his win rates on dirt, on grass, on turf; his jockey’s career record—there was no way, short of actually being able to see into the future, to predict any of the races. Each track offered the services of one or more handicappers, but they were no different from the hucksters he encountered on his beat as a financial reporter: the hedge funds that take a two-thousand-dollar commission and a twenty-percent performance fee for their worthless “management,” or the brokerages that win and lose fortunes throwing darts at the stock page of the Times.

Just then, Sol the Freud, the 5-2 favorite, charged passed us into first place, exactly as the handicapper predicted. Chris had bet him, it turned out; he shrugged and went to collect his pay out.


Photo: Ilya Lipkin

By two o’clock, the morning drizzle had thickened into a proper rain, so the three of us sought shelter in the Equestris Restaurant, the dining room for “high rollers” on the racetrack’s third floor. The moment we stepped inside, Ilya lit up. The restaurant’s elaborately folded cloth napkins, its potted fronds, and, above all, the artless reproduction of Géricault’s Riderless Races painted on the far wall could not have better suited his unfailing eye for the pathetic and the garish. While Chris and I split a turkey sandwich I had brought from home, Ilya criss-crossed the room, photographing everything from the scalloped ceiling to sea-foam green carpet—pausing, before each shot, to flash us a toothsome grin. Later, I read that, despite its chintzy trappings, the Equestris Restaurant was actually the largest restaurant in New York City when it opened in 1983 and that the gala was attended by quite a few celebrities, among them Warren Beatty, Andy Warhol, and even a twenty-four-year-old Michael Jackson, fresh from the success of Thriller. Glum as the dining room was now, thirty years had not dimmed that aura of exclusivity. Though the racetrack had no security guards to keep the rain-soaked gamblers out—indeed, judging by the omnipresence of malt liquor and the thick smell of marijuana indoors as well as out, the Aqueduct was rivaled only by the beach at Coney Island for lack of police presence—none of them ever ventured up into the restaurant. Besides us, the only other patrons were a white family from Long Island, quietly dividing a platter of lasagna served to them by a tuxedoed waiter with all the deference due a visiting head of state.

We watched the next races on the television installed at our table, a small white set nearly identical, I noticed, to the twelve-inch Mitsubishi Ilya and I had had in our bedroom growing up. It was amazing, Ilya said, just how boring horse racing was if you weren’t betting. The horses were practically indistinguishable; the commentary impossible to follow. And the snowy, soundless picture felt like a dispatch from purgatory, where, as punishment for a life of haste and inattention, some poor souls were doomed to ride and ride without ever getting anywhere.

Chris took a more sanguine view. Monotony, he said, was in the nature of every sport. One game always followed the next, season after season, year after year. No sooner had you won the Stanley Cup or the World Series than you were back where you started, 0-0. That was why he never understood fans who cried when their team lost or mailed death threats to a rival goalie. Nothing was permanent, neither victory nor defeat. The least you could say for the racetrack was that it was the one place in the world where a win was never celebrated and a loss was always suffered quietly. For all that, Chris conceded, it might make sense to leave a little early, as it was getting close to rush hour.

On our way out, we noticed that the crowd in the stands had nearly tripled while we were in the restaurant. The rain had let up, a few shafts of sunlight had broken through the low-hanging clouds, and nearly all sixty seats on the ground floor were taken. The crowd, it turned out, had gathered in anticipation of the final race of the day, the Jimmy Winkfield Stakes, though no one seemed to recognize it as such—they only called it “the race” or “the big one.” (“Who do you like for the big one?”) Our curiosity stoked, Chris and Ilya went to stake out seats, while I made my way over to the rail to stretch my legs. There, three squat men in FDNY caps carefully observed the warm-up of a fierce black colt on the inside dirt track. This was Charleymillionaire, and from their excited chatter, I gleaned that he was the favorite, and that the Jimmy Winkfield Stakes were expected to be the first big win in what was to be a distinguished career. It was not hard to see why the men were so impressed with him. Each step Charleymillionaire took made the ropy muscles bulge beneath his glossy coat. His tail swished back and forth furiously. Somewhere behind his eyes, it seemed like there must have dwelled an ancient memory of running unsaddled across a Spanish plain. When his jockey tugged at his reins, he gave an angry snort before complying.

I was just about to return to my seat, wondering how the other horses stood a chance against such a determined animal, when I caught notice of a chestnut gelding called Hot Heir Skier. A little smaller in stature than Charleymillionaire, he was doing a few light sprints right by the rail, taking no notice of the crowds or of the stands. (Between sprints, the other horses’ heads inevitably drifted toward the spectators.) He lifted one hoof and placed it down, and then another, and another, as serenely as the horses I had once seen on a drive to Vermont, with nothing to do but chew hay all day and watch cars zip by. His jockey hardly had to steer him—although, from time to time, he gave him a good thwack anyway. I’m the first to scoff when pet owners speak as if their dogs are human beings—and yet, as Hot Heir Skier came by the rail, swinging his head around ever so slightly, his shallow, button-like eyes were square with mine, and I looked at him, and he looked at me, and I was sure he was regarding me not just with animal curiosity but actually with pity—as though I were worse off than he for having no jockey to tell me where to go and how to get there.

I went to place a fifty-dollar bet on him, only to find the cashier shutting up as I reached the front of the line.

* * *

At first it seemed I had caught a lucky break. The moment the bell sounded, Charleymillionaire charged right out of the gate, leaving Hot Heir Skier boxed in at the rail by Otoy, a runty long shot. The colt’s tail whipped through the shower of dirt thrown up around him while the other horses trailed behind like guppies in the slipstream of a massive trout.

As the riders came around the bend, however, Otoy fell to the back of the bunch, giving Hot Heir Skier the room to glide out—still lifting one hoof serenely after another—in front of Oliver Zip. With the gelding hot on his heels, Charleymillionaire’s jockey began to whip him mercilessly, trying to preserve his lead. The more furiously he drove himself, he more and more he fell behind. Hot Heir Skier easily passed him in the home stretch, tossing his head with the same haughty unconcern he had showed me. Oliver Zip took second place, followed by Pax Orbis. He and Charleymillionaire finished so closely together that it took a photo review to establish that Charleymillionaire had finished out of the money. Had I successfully bet on Hot Heir Skier to win, I would have collected eight hundred dollars.

Chris and Ilya and I filed out with the rest of the crowd. Looking from face to face, all of them almost beatific in their expressionlessness, it seemed I was not the only person at the Aqueduct that day to receive an object lesson in stoicism.

Acceptance, of course, must go hand in hand with forgetfulness. Apart from a tiny notice in the racing form, no announcement had been made that the race just run was the Jimmy Winkfield Stakes—and apart from a display case in the lobby filled with dingy, fake-looking trophies, the only indication that there had even been races at the Aqueduct before that day was the Wood Memorial Wall. Here, in a lightless corner behind one of the staircases, four-by-six-inch photographs showing winners, jockeys, trainers, and owners were crowded floor to ceiling like the paintings in a French salon. Most of the gamblers at today’s race had, in all likelihood, seen some of these victories; still, not a single man stopped to pay his respects. One would think that a place so thoroughly relegated to the past might be more mindful of what has come before.

The death knell has already sounded for the Aqueduct—soon, not one, but seven casinos offering blackjack, poker, craps, and live entertainment will open all over New York State. Nostalgia comes with old age—why not look back? But to be of the past is not the same as to be in the past. A regular at the Aqueduct stands with one foot in a glum today and one in a sunny tomorrow. Today he doesn’t have two nickels to rub together; tomorrow, his horse has won by a nose, his pockets are full of money and his family has forgiven him for his failures as a husband and a father. Soon, he will be gone and the men beside him in the stands, men who can’t even recall the name of a horse that accomplished the astounding feat of winning the Triple Crown while undefeated, will hardly remember him who has done so little. It is a pleasant place, the Aqueduct. Go while it’s still standing.

Michael Lipkin is a student and writer living in New York City. His writing has appeared in n+1The Nation, and The American Reader.