Serendipity

Jermaine is a fixture at the Old Hilltop. He isn’t anyone’s employee, but all the trainers respect his presence; it’s a rare morning when he isn’t at the clubhouse turn of the track at the crack of dawn, watching the early workouts with a stopwatch in hand. He jots down the racers’ times in a little black notebook, which he keeps in the inside pocket of his tattered overcoat. When he goes to make his bets, the bookies greet him by name. He keeps all conversations short and to the point. The employees at Pimlico Racecourse know better than to try and chat with Jermaine Montgomery, the bitter old man who only talks to the horses.

Other sharps gather at the rail and pore over pedigrees, keep careful notes on breezes and soundness and past performances. Jermaine does that too, but there’s more to his method. In his notebook, he scrawls the clockings, then adds the oft-overlooked details that can mean more than the numbers. Big chestnut hates figure-eight. Number four has wrong jockey. And, on a brisk morning two days before the Preakness Stakes, grey filly wants to win.

Jermaine's notebook is Pimlico’s holy grail. So when it goes missing before dawn on Preakness day, his wrath breaks the hazy peace that lingers over the racetrack before the crowds arrive. He storms through the stables, shouting.

“Whatever sonofabitch stole my notes--I’ll gut you like a fish, you dirty, cheating bastard--!”

The grooms scatter, tossing down their pitchforks and hurrying lithe Thoroughbreds into their stalls. Nobody meets Jermaine’s furious gaze. His face feels red, like the roses they put on that bay colt back in Kentucky.

After a few minutes, two grooms stop him in his path, frog-marching a kid between them--one of the track rats Jermaine has seen around the backside, a scrawny teenager with shaggy black hair that hangs over his eyes. The kid keeps his dark eyes to the ground.

The grooms dump him in front of Jermaine and hurry back to their tasks. Shakily, the kid holds up the notebook, and Jermaine snatches it away.

“They told me you’d know every winner.” The kid stares at the ground, his voice sullen, and Jermaine’s anger falters. “I need the money. I need to win.”

Jermaine doesn’t like people, but he can’t stay mad at a kid. “You’re too young to bet.”

“My older cousin gets the ticket for me. I’ve saved over three hundred dollars, just from the races.”

There’s some strange determination in the kid’s eyes, and Jermaine relents, softened--maybe he sees himself in that touch of pride. “You want some advice? Come with me.”

***

“So,” Jermaine asks gruffly as they walk, “who was your pick?”

The kid scurries after him, trailing sweatshirt sleeves several sizes too long. “I was gonna put it on Lasting Tradition.”

The colt who won the Kentucky Derby. The morning line favorite, a rangy bay with no markings, well over sixteen hands tall. Yesterday, Jermaine clocked his four-furlong breeze. His note beside the colt’s name reads, good horse.

“Won’t make any money that way,” Jermaine mutters, pulling the brim of his hat down. “Chalk players don’t get the big payouts. Gotta take a risk.”

“You never bet on the favorite?”

“Sometimes. But not when I think he’ll lose.”

The kid turns on him with round eyes. “You think he’s gonna lose?”

“Keep it down.” Jermaine scowls at the kid. “He might lose. I’m not a psychic.”

“But you think he will! How can you tell?”

Jermaine hesitates. Finally, he says, “You’ve made your money betting favorites. If you don’t wanna risk it, put your money on the colt.”

“Not if he’s gonna lose--this is all I’ve got. I can’t lose.” The kid wrings his hands together.

With a sigh, Jermaine stops and turns to face him. “You sure you should be here, kid?”

The kid looks uncomfortable for a second, out of place in that oversized sweatshirt and torn jeans and the racetrack concourse and his own skin. He doesn’t answer.

“You’re not gonna keep your money betting horses,” Jermaine says.

“I have to.”

“Get a job.”

“I can’t.” The kid won’t meet his gaze. “I need a lot of money. Thousands.”

“What could you possibly need that much for?”

The kid mumbles something, so quiet Jermaine can’t hear. He leans in, placing a rough hand on the kid’s shoulder.

“Say again? Old ears.”

“I’m a girl!” It’s a sudden confession, loud, and immediately, the kid looks mortified.

Jermaine takes a step back. “Say what?”

“I’m--I’m a girl.” Firmer, like a mantra. Say it bold, make it so.

“You don’t look like no girl.”

“That’s why I need to win, Mr. Montgomery.” There are tears in the kid’s eyes. “I wanna be a girl. Only my cousin knows--but my family isn't gonna help me. I have to get the money myself.”

Jermaine considers this in silence. He’s heard about this before, seen magazine covers with famous transgender folks on them. But this sniffling kid in front of him is no pop star, just a terrified child.

“What’s your name, kid?” he asks at last.

The kid wipes her eyes on her baggy sleeve. “Diego.”

“That’s no name for a girl. What’s your real name?”

She looks at him like she’s seeing him for the first time. It takes a second before she recovers from her surprise and stammers, “D-Daniella.”

Nodding, Jermaine straightens and sets off again. The kid stands rooted to the spot behind him; without looking back, he lifts a hand and gestures to her. “You comin’, or what?”

She takes a sharp breath, and he can hear the scraping of her sneakers against the asphalt as she follows him.

***

Daniella hesitates outside the stakes barn, and Jermaine can see why; there’s a flurry of activity in the aisle, press and eager racegoers alike crowding the green plank walls to get a look at the Preakness hopefuls stabled there. Jermaine doesn’t stop. There’s a reason he’s here now, while the throngs of strangers are occupying the space. No hobbyist will think much of an old man in a flat cap bringing a teenager up to a horse’s stall, but if the other handicappers saw, they might take notice.

Jermaine walks past the stalls of racing’s fastest colts without bothering to pause and look them over. There are some fine animals here, the products of centuries of careful Thoroughbred breeding and lifetimes spent dedicated to the art of training a racehorse. None of them take his interest. He spares a glance at Lasting Tradition--a Derby winner is a Derby winner--but keeps moving down the shed row until he reaches the one he wants.

The dappled grey filly has her elegant head snaked over the plastic barrier in front of her stall. Her ears are pricked forward with interest as the old man and the track rat approach; she’s alert, but not skittish, bold, but respectful. She’s a compact horse, not much more than fifteen hands at the withers, but there are muscles rolling beneath her sterling coat.

Daniella steps towards the stall with an outstretched hand, and the horse reaches her soft nose towards the trembling fingers. The kid seems uncertain around the animal, but she pushes past the hesitation and strokes the white stripe on the filly’s face.

“They’re gonna rule her out for her size, and for the fact that she’s a girl running against the boys." Jermaine flips open the notebook. “She’ll go off at high odds. You might just make something.”

Daniella looks at him over her shoulder as the filly nips the strings hanging from her hoodie. “You really think she’s gonna win? How can you tell?”

Jermaine cracks a smile. He’s not used to smiling; it creases his worn face, but he’s surprised to see the kid smile, too. “She’s got the fire,” he says, lowering the notebook so that Daniella can read the smudged writing. “When she gets out there, she’ll put it all down. I watched her in her workouts--filly gave it her all, every time. When you know, you know. But it’s a risk, I won’t lie to you. You chance it on a long shot, you might lose your money.”

Daniella’s gaze returns to the silver Thoroughbred, who has lost interest in the cotton strings and has turned her attention to the crowd gathered outside of the Derby winner’s stall. Her nostrils are flared. She paws at the ground, metal-shod hooves scraping away sawdust from the concrete. Daniella is contemplative as she scrutinizes the filly. Jermaine reads people like he reads horses, and he sees in both of them the look of eagles.

“What’s her name?” Daniella asks.

He consults his notes. “Serendipity.”

***

Jermaine helps Daniella’s older cousin at the betting booth, guiding her through the process. Together, they take the ticket--three-hundred-forty-three dollars, Serendipity to win, odds at sixty to one. They make their way to the concourse, push forward to the rail. It’s a big bet. If the filly wins, the payout will be twenty thousand dollars.

When the bell sounds and the horses surge from the gate, Serendipity gallops to the outside of the pack, stalking the frontrunners like a silver shadow. Up through the clubhouse turn, the jockey keeps the horse under wraps, holding back the onslaught of speed that Jermaine knows she can’t wait to unleash.

In the backstretch, the infield blocks their view, and they look to the big screens to watch the horses jostling for position. The announcer calls blistering fractions--the first quarter in twenty-three and four, the half in forty-six and one. The filly doesn’t yield. Jermaine knew she wouldn’t. She digs in and holds on.

As the horses enter the far turn, the noise from the crowd swells, and there’s a tension on Jermaine’s wrist. He looks down to see Daniella gripping his arm, viselike. All of her money is on the line, every penny that she has scrounged up, and he can see the fear in her eyes as the horses fly into the most grueling portion of the race.

As they round the turn and hit the top of the stretch, Lasting Tradition is in the lead. The plain bay's ears are turned back towards the stampede in pursuit of him, but he’s clear by two lengths as he makes for the finish.

Jermaine expects the filly’s turn of foot before he sees it. She’s still on the outside; she came through the turn three-wide, but kept going, her strides lengthening. She’s focused ahead. He can see it in her eyes again, that she sees the colt ahead and wants nothing more than to chase him down, to catch him. The jockey shakes her up, flings the reins and gives a single swing of the whip, and she starts to run down the favorite.

Daniella’s face goes slack as she processes what’s happening. Then the kid catches her breath and bounces onto the balls of her feet and shouts, her grip on the old man’s arm tight to the point of pain, but he doesn’t pull himself free--just shouts with her, voices rising above the din of the crowd.

Serendipity pulls forward until she’s eye-to-eye with the colt. To her outside, the big bay towers over her; his jockey is fierce with the crop, calling on every ounce of horsepower within his mount. For an instant, the filly seems to hesitate as she stares down her burly rival, their strides locked.

The colt is a good horse. But the grey filly wants to win. She takes the bit, drives her head down, and surges to the front.

Daniella is laughing, tears streaming down her face as Serendipity blazes under the wire, the leader by a length, the winner of the Preakness. Jermaine claps her on the shoulder with a wide grin. His face aches from smiling. He’s been picking winners for years, but it’s never felt this good.

“What’d I tell you, kid? It’s a good day for the girls.”