The Winner's Circle
Story Written in January, 2023 for NYC Midnight Fiction Contest
January, 2023
The Winner’s Circle
Bobby is desperately trying to please his father and show he can be a con man too. At the race track, he and his buddy Pete have a fool-proof plan to get Bobby that satisfaction.
Bobby never thought he had the respect of his father, one of the great Gotham con artists. The man Bobby called dad chided him for still being a junior accountant at the Daily Mail. Granted, Bobby was in his mid-twenties and nothing more than a pencil-pusher for the newspaper. He was searching for the right chance for a big score. Then he could strut in front of Papa.
“Hey Bobby, how’s it hanging?”
“Todd, what’s new in the sports department?”
Bobby hated the way Todd treated him but knew that he had to keep those thoughts to himself. Todd’s father was a senior accountant and controlled Bobby’s future.
“Can you keep a secret?”
“I guess. What kind?”
“I’ve got a live one this afternoon at the track. Fifth race. Trainer has been stiffing it the last few starts, looking for long odds today.”
Bobby was interested. His dad regularly played the ponies. This could be the moment he was waiting for. But he didn’t want Todd to sense his excitement.
“Sure, I’ve got a couple of extra dollars, maybe I can get there.”
Todd looked around the newsroom, then bent into the cubicle.
“Bet it on Macon Whoopie. Remember that name. Fifth race. But you can’t tell anyone else.”
“Thanks, Todd, my lips are sealed.”
After stopping at the bank to withdraw a substantial chunk of savings, Bobby entered the track with an air of confidence. He knew something no one else did.
“Hi Mabel,” Bobby said to his favorite teller.
“Bobby! Haven’t seen you here in a while. Your dad is upstairs in his box. He’s been killing it. Seems like he can’t miss.”
“Like father, like son Mabel,” Bobby said quietly. “Put it all on Macon Whoopie in the fifth.”
Taking his ticket from Mabel, Bobby sauntered out of the grandstand toward the rail, wanting to be at the finish line when his investment crossed first.
“Hey Bobby, wait up.”
Turning around, Bobby saw his friend, Pete, a track regular, who usually lost more than he won. He was known as Three-Finger Pete after a paper-mill accident when he was in his teens.
“You here to see your dad, he’s upstairs.”
“No. Here to catch a live one. Macon Whoopie.”
“That nag has no chance. Hope you didn’t bet a lot.”
“Only half my savings. I got a tip that the trainer has had the jockey keep him under wraps.”
“He hasn’t been under wraps. The horse is just slow. But I’ve a way for us to make it big. Real big.”
They paused as the fifth race started, and they watched Macon Whoopie run the entire race behind the field, finishing last. Bobby’s ashen face hung low for a moment, then hearing celebration, he looked up to see his father high-fiving his box mates. At the table next to him was Todd and his father, both laughing as they saw Bobby.
“As I was sayin’ kid, I’ve got an opportunity, and need you. It can be our big score.”
Bobby couldn’t stand the humiliation another day.
“Whatever it is Pete, I’m in.”
—-
That night over drinks, Pete described his plan.
The Derby was on Sunday. The heavy favorite would be Cloudy With Showers, an excellent thoroughbred. There was only one horse in the country who could beat Cloudy, and he wasn’t running. Dam Perfect was as fast a horse as there was around. However, he was resting in a nearby stable, not entered. Dam Perfect’s owner Ellery had brought the horse across the country to win the Derby. However, the day after he arrived, Ellery was discovered in the announcer’s booth, getting cozy with the track manager’s wife. The cuckolded manager made sure that none of Ellery’s horses would ever run at his track.
“Dam Perfect would mop up every horse in the Derby,” Pete confidently announced.
“How does it affect us?” Bobby wondered aloud.
Pete related that afternoon’s lunch with his second cousin, Vic, who worked as a hot walker at the stable where Dam Perfect was stationed until heading home the following week.
“Hot walkers are wise. They are visiting stables picking up all sorts of information that the rest of us don’t know. Vic said that Dam Perfect looks exactly like the slowest horse in the Derby. Like exactly. Same gray color and identical markings.”
“So, lots of horses look alike. I can’t tell them apart.”
“Do you know how horses are actually identified? They have a number tattooed on their upper lip. And Vic says Dam Perfect’s number is almost identical to a horse in the Derby called Dandy Surprise. Same digits, except Dam Perfect’s last digit is an 8 while Dandy Surprise has a 6. Vic says Dam Perfect’s tattoo is fading away and looks like a 6. Like they were twins, except one is a helluva lot faster than the other.”
Bobby picked up on Pete’s breadcrumb trail. He wanted to switch horses and have Dam Perfect run the Derby in place of Dandy Surprise, hoping the stewards would look at the lip as the horse was getting saddled and not know any difference. Neither would the betting public, meaning Dandy Surprise would go off as a long price.
"The Derby is Sunday, we'll do the swap on Saturday night. Get me around 10. "
"You sure about this Pete?"
"We’ll be meeting in the winner’s circle Bobby."
—
They arrived at Dandy Surprise’s stable. Since the only horses there were old and slow, humans were absent. The owners hoped their horses ran away or got stolen, maybe getting an insurance settlement. Getting out of the car, it dawned on Bobby that they were missing something.
"Pete, how are we getting the horses to each barn? I don't have a trailer on my car."
This bit of information caused Pete to pause. Transportation was something he hadn’t prepared for. But it wasn't going to deter the mission.
"You know how to ride a horse?"
Bobby stared Pete down.
"Okay. You can’t. We’ll both jump on him and ride. How hard can it be? Now let's get this done."
The barn was dark and had the same odor Bobby remembered from visiting stables when he was young. He could sense despondent life around him. Raspy breathing filled the cool air, these horses were hard-knockers like him.
"Third stall on the right, that's what Vic told me," Pete whispered.
It was enough noise to rustle the horses. Bobby's eyes were now adjusted to the lack of light and could see equine eyes, confused at the unusual nocturnal activity.
"Here we go. Check him out," Pete announced, using a louder voice as each flipped on a flashlight.
They were staring at a gray colt with a distinctive black stripe from between the ears to the tip of the nose. Until that moment, all horses had appeared the same to Bobby - betting opportunities. They were nothing but names and numbers in the Daily Racing Form. This was the first time Bobby was face-to-face with one. It brought him a sense of peace. Sure, Dandy Surprise had only won one race in his life, two years prior. But there was an instant connection with Bobby, a shared sense of failure.
Pete broke the silence.
"It's a couple of miles and I know the way, so how about you focus on riding while I tell you which way to go. Plus I only have a few good fingers."
Bobby surprised Pete by agreeing. It would give him time to lean forward and be closer to his new friend. Dandy Surprise would make sure Bobby had a smooth ride.
Getting Dam Perfect out of his barn would be a challenge because there was a security guard. It was decided that Vic would distract the guard. Once the horse robbers were within viewing distance of Dam Perfect's barn, Pete ordered them to halt. He took binoculars out.
"Pete, you remembered binoculars but not a trailer?"
"Shut up, be quiet. I can see Vic talking to the guard outside the barn. Looks like the guard doesn't want to leave. Oh, Vic just pulled out a joint. Good job Vic. You can't smoke near all that hay. Head down by the river."
Bobby could see two shapes moving away from the barn. It was time for action. The two quietly got to the barn and Bobby led his new friend inside. Immediately Bobby knew they were in a different world. The smell wasn't as raunchy and each horse had its own nameplate on the swinging half-door. It had the feeling of royalty, not simplicity.
Seeing Dam Perfect, Bobby couldn’t believe how alike the two horses were. Pete grabbed the reins of the champion and led him away.
“While I’m settling this one outside, put that rat in the stall. We need to get out of here quick.”
“He’s not a rat Pete. Look at him. There is something about him that makes me happy. We are like brothers from another mother.”
Bobby put Dandy Surprise in the stall, patting his flank..
“Hey buddy. I’ve got to go. Thanks for the ride.”
Dandy Surprised whinnied a bit, continuing to make eye contact with Bobby. It was like the two of them were holding a silent good bye.
“Get your ass out here. We need to escape.”
Bobby patted Dandy Surprise on the forehead.
“Maybe we’ll meet again,” was the unspoken message.
—
After the horse trade, he was too energized to get any rest. This was going to be the day he would be remembered in betting circles. The Great Switcheroo. Maybe, just maybe, his father would bring him on board so he could quit the stupid accounting job and be able to spend his days at the track, the two of them being a real father and son. Bobby had enjoyed being at the track the past few days. Being on a horse earlier in the evening was a thrill. Pete had called him a natural. And there was the bond he had forged with Dandy Surprise. Now he understood why people worked in the business despite the miserable conditions and pay, there was an existential reward.
The track was buzzing with excitement when Bobby entered. He waved hi to Mabel, who was busy taking bets. The crowd was the largest he’d ever seen and everyone was there to bet Cloudy with Showers. He and Pete agreed to make a series of smaller bets throughout the grandstand instead of one large sum, to stay under the radar. He had about an hour until post time.
“Hi Mabel, can’t believe the amount of people here.”
“It’s our big day here Bobby. Lots of money being wagered.”
“Everyone betting Cloudy with Showers in the big race?”
“So far. Still an hour to go, but looks like he’s the heavy choice.”
“Anyone mention Dandy Surprise?”
Mabel let out a chuckle. “Only you would be the person to be on that horse. He’s at 150-1 right now.”
“I know,” laughed Bobby, still not wanting to give his secret away. “But I’ll live up to my reputation and put $100 to win on him.”
“Just more for the rest of us,” said Mabel as Bobby winked at her.
For the next half hour, Bobby made the rounds, making $100 bets. He ended up at the paddock with Pete and Vic. They snuck him past security to watch as the horses were getting saddled up.
“This is the moment,” Vic whispered. “The stewards are coming around to do the lip check.”
The three of them froze while a man in a white suit went from horse to horse, lifting up each one’s lip. When they reached the horse wearing the colors of Dandy Surprise, Bobby couldn’t watch. He turned around, ready to vomit.
“I knew it.” Bobby heard Vic say. “Easy. They could care less about Dandy Surprise.”
Bobby turned and saw the stewards moving to the next competitor.
“We did it. Now let’s finish getting our bets in. About 15 minutes before they start,” Pete said.
Bobby stopped for his last bet, the rest of his savings.
“Hey Mabel, $100 more on Dandy Surprise, I sense an upset.”
“Gotcha. Funny, you must know something. A few other guys were just here and bet on Dandy Surprise. Some guy named Ellery dropped a hefty amount.”
“Wait. Ellery?”
Before he could get a response from Mabel, Bobby rushed to the track where the horses were starting to parade in the final minutes. He forced his way to the front to get a close up of Dandy Surprise. When the jockey brought the horse to the rail, Bobby looked into the horse’s eyes. Maybe Dandy Surprise and Dam Perfect looked the same to the naked eye, but no one else knew the relationship that Bobby had with the slower of the two.
“Don’t put money on me.” That’s what the horse, his friend, was telling Bobby as they stared at each other.
It was clear. The horse on the track was the real Dandy Surprise, not Dam Perfect.
Up in the boxes, Bobby saw Ellery sitting quietly, surrounded by other rich people, both smug and jovial.
Bobby felt helpless, desperately looking for Pete or Vic. The wrong horse, actually the right horse, was running the race. He considered ripping his tickets right there.
“And, they’re off,” cried the track announcer.
Immediately, Dandy Surprise went to the back. At no point during the race was he close to the front where Cloudy with Showers was battling two others. Bobby was at the rail as the horses galloped to the finish line. Dandy Surprise, the clear caboose, turned his eyes to look at him, apologizing.
In the box seats, Ellery was screaming at someone, throwing his hands up in a questioning manner. Bobby could hear him yelling, “what happened?” Nearby, Bobby’s father had his arms overhead, in victory position, ready to cash another trifecta.
“Bobby,” Vic shouted, looking as white as a ghost. “Before the race I was at the bar, doing some early celebrating and bought a few whiskey shots for the security guard from Dam Perfect’s barn. He whispered that Ellery knew the similarities in horses and had swapped them himself just before dawn.”
—
Bobby looked again at his father. He had never really wanted to be part of the organization, just to have a normal relationship. Looking to his right, he saw Dandy Surprise being walked back to the paddock. Jumping over the rail, Bobby approached the groom who was being bombarded with catcalls about how awful the horse ran.
“I’m the new walker. Owner asked me to walk him back. Said he’s got a drink for you at the bar.”
The groom was only too happy to leave Bobby with the horse. Dandy Surprise had put forth a gallant effort and Bobby stroked his mane in gratitude. Maybe the thoroughbred business was for Bobby.
“Let’s go pal. We’ll find the winner’s circle. Together.”