Winning Streak
Winning Streak
"All that matters on the chessboard is good moves. - Bobby Fischer "
The coffee shop buzzed with the usual chatter, clinking mugs, and jazz playing low in the background. At the far corner, under a dim lamp, sat Theo—shoulders hunched, eyes narrowed over a weathered wooden chessboard. His black hoodie hung loosely on his lean frame, and next to him sat a tall mug of black coffee, untouched and going cold. Across from him, his latest opponent—a middle-aged man in a tailored suit—stared at the board, visibly frustrated.
“Checkmate,” Theo said quietly, barely loud enough to be heard over the background noise.
The man sighed, leaned back, and offered a reluctant smile. “Well played.”
Theo gave a small nod, then began resetting the pieces in silence. His fingers moved with the speed of someone who had done this a thousand times before—because he had. Sixteen games in a row, no losses. Most were quick, brutal takedowns. Others, like this one, dragged on for over an hour. But the result was always the same.
“Next?” he asked, his voice soft, but with an edge.
He didn’t need to look up. He knew there would be someone waiting. There always was.
A teenage girl with a backpack slung over one shoulder stepped forward. “I’ll play,” she said, sliding into the seat. “Heard you’re on a streak.”
Theo gave a slight shrug and gestured for her to take white. “Your move.”
The café had become something of a local legend ever since Theo started showing up six weeks ago. No one knew much about him—just that he arrived at 2 PM every day, ordered the same coffee, and challenged anyone to a game. Winner stayed, loser walked. If he lost, he’d leave the board for a week. But he never had to. Not yet.
“You play online?” she asked, moving her queen’s pawn forward.
“Used to,” Theo replied, responding with his knight. “Stopped after I got bored.”
She snorted. “Bored? Who gets bored of online chess?”
“People who stop losing.”
Her eyebrows lifted. “So, you’ve never lost?”
“Not in a while.”
Their game unfolded quickly. She was sharp—clearly a student who played competitively. Theo recognized a few of her lines, the kind you'd learn from online tutorials or chess camps. But she was rushing. Too eager. That was always the giveaway. People played differently when they thought they had something to prove.
Fifteen minutes in, she made her mistake—overextended a bishop to pin his knight. It looked aggressive, but Theo saw the sequence three moves ahead. He baited the trap, sprung it, and picked off her center pawn. She frowned, hesitated, and then played a rook.
Too late.
“Checkmate in five,” Theo said quietly.
Her eyes darted across the board, searching. “No way.”
He waited.
Four moves later, she slumped back in her chair, sighed, and said, “Fine. Show me.”
Theo calmly played the final sequence. Her king was boxed in, nowhere to run. She stared at the board for a while, then shook her head.
“You’re like… a machine,” she said. “You don’t even celebrate. You just win.”
“I don’t play to celebrate,” Theo said. “I play to remember.”
Her expression shifted. “Remember what?”
But Theo was already resetting the board.
It hadn’t always been like this. Before the streak, before the café, before the silence, there had been life. Real life. Theo and his twin brother, Leo, had grown up playing chess together. They were inseparable—mirror images of each other on and off the board.
Leo was the better player, or so it had seemed. More aggressive, more daring. But Theo had always been steady, methodical, a slow-burning storm. In high school, they joined tournaments, competed in state championships. The finals were always a toss-up between the two. And then came the accident.
A rainy night. A speeding car. Leo, on a walk, headphones in. Gone in seconds.
Theo didn’t speak for weeks.
Chess was the only thing that made sense afterward. Not school, not friends, not therapy. Just the board, the pieces, the rhythm of the game. That’s when he started showing up at the café. A place Leo loved. A place where they’d played casual games on rainy Saturdays.
Theo didn’t play to win. He played to feel Leo on the other side of the board. Every move was a memory, every defense a conversation they never finished.
The afternoon wore on. Theo played three more games. Three more wins. The sun had dipped below the horizon, painting the sky in burnt orange. He was about to pack up when someone new walked in. Older, maybe mid-fifties, with a gray beard and a black coat. He moved with quiet confidence and carried a small roll-up chess mat under his arm.
“I heard about you,” the man said, pulling up a chair. “Mind if I sit?”
Theo nodded.
The man unrolled his mat but paused. “I prefer to use my own. Habit.”
Theo understood that. Respect.
They set up the pieces, and the game began.
The man was different. No nerves. No desperation. His openings were classic refined, like someone who had been playing since long before Theo was born. Theo leaned in, more alert now. Finally, an opponent who didn’t rush.
As the match drew on, a crowd formed. Regulars, curious onlookers, and the café staff gathered around. They could sense something unusual. Theo was sweating now, for the first time in weeks.
The man pinned Theo’s knight.
Theo castled.
The man sacrificed a rook.
Theo hesitated.
Ten more moves. The tension thickened. The café seemed to hold its breath.
Then, the man whispered, “Checkmate.”
Theo froze.
It was true. Somehow, through perfect positioning, the man had cornered him. No way out. No tricks left. Just silence.
For a long moment, Theo stared at the board. Then, slowly, he smiled. The first real smile in months.
“Who are you?” he asked.
The man leaned back, eyes kind. “Just someone who lost his brother too.”
Theo looked up sharply.
“I saw you here weeks ago,” the man continued. “I recognized that look. The way you play. Like you’re chasing something.”
Theo nodded, throat tight.
“Grief doesn’t go away,” the man said. “But it changes. Sometimes, a loss can teach you how to win differently.”
Theo stood and extended his hand.
“Thank you,” he said.
The man shook it. “You’ll be back.”
Theo looked around the café, now dim and quiet. “Yeah. But not for a streak.”
And for the first time in a long while, he walked out without needing to win.
Winning Streak was never about the wins. It was about remembering who he was when he still had someone across the board—someone worth losing to.
*** I used to be a tournament director for a USCF club. One of my predecessors liked to create stories based on the players and the results of the event. Thank you for reading!!
