Risky Business

Over the next ten days we will be publishing the ten finalists from the 2023 Voorheesville Short Story Contest. The theme of this year’s contest was “A Roll of the Dice.” This, the first of our ten finalist stories, made it to the final round of judging with our guest judge, Laurin Jefferson. Today, enjoy Wiley Dawson-Bilby’s story, “Risky Business.”

Jack had always been a bit of a gambler. He liked the thrill of taking a risk and the possibility of winning big. When he was younger, he would play cards with his friends and bet on the outcome of sports games. It was harmless fun. But then he got married and had a kid. He still liked to gamble, but it became less of a hobby and more of an addiction. He would sneak away to the casino or place bets online, hoping to hit it big and give his family a better life. But the more he gambled, the deeper he dug himself into debt. His wife, Sarah, knew about his gambling, but she thought it was just a harmless habit. She didn’t know the extent of his addiction, or how much money he was losing. Jack didn’t want to worry her or burden her with his problems, so he kept it a secret. One day, Jack got a call from an old friend. The friend had a tip on a horse race that was going to take place that weekend. The odds were in their favor, and if they placed a big enough bet, they could win a lot of money. Jack hesitated at first, but the lure of a big win was too strong to resist. He agreed to meet his friend at the track and place a bet on the horse. When Jack arrived at the track, he was greeted by his friend and a few other guys he didn’t know. They were all there to place bets on the horse. Jack handed over the money he had saved up for his son’s college fund and placed a bet on the horse. The race was intense, and the horse they had bet on was in the lead for most of it. But in the final stretch, another horse came out of nowhere and took the lead. Jack watched in horror as the horse they had bet on lost by a nose. He had lost all the money he had saved for his son’s future. He tried to hide the truth from his wife, but she found out eventually. She was furious and hurt that he had gambled away their son’s college fund. Jack promised her that he would stop gambling and make things right, but he couldn’t shake the urge to take another risk and try to win back what he had lost. He started sneaking off to the casino more often, spending more and more money on bets. He told himself that he was just trying to break even, but he knew deep down that he was digging himself into a deeper hole. One night, Jack was at the casino playing craps. He had lost most of his money, but he was determined to keep playing. He placed a big bet on the next roll of the dice and watched as they tumbled across the table. He had a sinking feeling in his stomach as he saw the outcome. He had lost everything. He stumbled out of the casino, feeling defeated and hopeless. He didn’t know how he was going to explain this to his wife, or how they were going to pay their bills. He felt like a failure as a husband and father. As he was walking down the street, he saw a homeless man sitting on the curb, shaking a cup of change. Jack felt a twinge of guilt as he realized that the man probably had more money than he did at that moment. He approached the man and asked him if he wanted to play a game of craps. The man looked at him skeptically, but Jack insisted. He pulled out a pair of dice and explained the rules of the game. The homeless man shrugged and agreed to play. They played for a while, and Jack felt a glimmer of hope as he started to win. He had a lucky streak, and he was able to turn a few dollars into a hundred. As Jack and the homeless man continued to play, Jack felt a sense of excitement and possibility that he hadn’t felt in a long time. He was winning, and he was good at the game. He felt like he had a chance to make things right. But then the tide turned. The homeless man started winning, and Jack began to lose again. He felt his heart sink as he watched his stack of chips shrink down to nothing. Just when he thought it was all over, the homeless man did something unexpected. He offered to give Jack some of his winnings back. “I’ve been in your shoes before,” the homeless man said. “I know what it’s like to lose everything. But sometimes, you just need someone to give you a helping hand.” Jack was taken aback by the man’s kindness. He realized that he had been so focused on his own problems that he had forgotten about the struggles of others. He took the money from the homeless man and thanked him. As he walked away, he felt a renewed sense of hope. Maybe there was a way out of this mess after all. Over the next few weeks, Jack worked hard to make things right with his wife and son. He got a second job to help pay off their debts, and he started going to Gamblers Anonymous meetings to get help for his addiction. It wasn’t easy, but he was making progress. He had the support of his family, and he was starting to feel like himself again. One day, he received a letter in the mail. It was from the homeless man he had played craps with. Inside was a check for the exact amount that Jack had lost at the casino that night. “I never forgot what you did for me,” the letter read. “You gave me a glimmer of hope when I needed it most. I hope this check can do the same for you.” Jack was stunned. He couldn’t believe that this man, who had so little, would be willing to give so much. He was touched by the gesture and grateful for the reminder that kindness can come from unexpected places. As he looked at the check, he felt a sense of closure. He had learned a valuable lesson from his addiction, and he had come out the other side a better man. He was determined to use his experience to help others who were struggling with the same issue. Years later, as he watched his son graduate from college, he felt a sense of pride and joy that he couldn’t put into words. He had taken a gamble with his family’s future, but he had rolled the dice again and come out on top. He knew that the road had been difficult, but he also knew that he had made the right choice. He had taken a chance on himself, and he had come out the other side a better person. And for that, he would always be grateful.

About Wiley Dawson-Bilby 426 Articles

Wiley Dawson-Bilby is a junior at Clayton A. Bouton High School.