Philadelphia Chess Master Greg Shahade Ends Jamie Ding's 31-Game Jeopardy! Streak

Key facts

• Greg Shahade defeated Jamie Ding on Jeopardy! on Monday night.
• Ding had won 31 consecutive games and nearly $900,000 in winnings.
• Shahade won by $13,990.
• Shahade is an International Master in chess, one level below Grandmaster.
• His sister Jen Shahade is a professional poker player and former U.S. Women's Chess Champion.
• Shahade found all three Daily Doubles and bet aggressively, citing an 83% success rate on practice questions.
• The taping took place in January 2025; Shahade took the online test in August 2024.

A Stunning Upset on the Set

On Monday night, Greg Shahade, a 41-year-old chess International Master from Philadelphia's Rittenhouse Square, ended Jamie Ding's 31-game winning streak on Jeopardy!. The victory was decisive: Shahade outscored Ding by $13,990, a margin that rendered the Final Jeopardy round a formality. Ding, who had accumulated nearly $900,000 over his run, was finally toppled. Shahade watched the episode at his sister's home in Philadelphia, surrounded by family and friends. His nephew, distracted by the Flyers game playing on another screen, barely noticed the historic moment. For Shahade, the win was the culmination of a journey that began just a few years ago when he first took the online Jeopardy! test.

From Chess Board to Trivia Stage

Shahade's path to Jeopardy! was methodical. He took the online test several times before being invited for a second test in August 2024. After passing that, he underwent an interview to assess his on-screen presence. In January 2025, he was invited to tape the show. On the day of taping, names were drawn randomly to determine the order; Shahade was selected for the first game of the day. Despite his nerves, Shahade excelled at the buzzer during the practice round. He credits his success to extensive preparation: playing practice games online and studying old episodes. But he also acknowledges the role of luck. 'There's an alternate universe where I show up and get totally crushed,' he said.

Aggressive Betting and a Nail-Biting Daily Double

Shahade's betting strategy was central to his victory. He found all three Daily Doubles and bet aggressively on each, including a crucial all-in wager on a clue about Oscar Wilde. 'I knew I was going to go all in,' Shahade said. 'In my training, I get the Daily Doubles right about 83 percent of the time, which is a very high number.' One Daily Double nearly undid him. The clue asked for the name of an Oscar Wilde play; Shahade knew the play but could not recall the title. As time ran out, he mentally cycled through Wilde's works and finally blurted, 'What is Lady Windermere's Fan?' He was correct, and the bet paid off. 'I was really panicked,' he admitted.

A Chess Family's Influence

Shahade comes from a family steeped in chess. His sister, Jen Shahade, is a professional poker player, a two-time U.S. Women's Chess Champion, and author of the book Thinking Sideways: How to Think Like a Chess Player and Win at Life. His father is a four-time Pennsylvania state chess champion. Shahade himself holds the title of International Master, one step below Grandmaster. Beyond chess, Shahade is an avid CrossFit enthusiast, training at CrossFit OBA on Washington Avenue and Orangetheory in Center City. His diverse interests, he said, helped him stay calm under pressure.

The Final Jeopardy and What Comes Next

By the end of Double Jeopardy, Shahade had more than double Ding's score, effectively locking the game. All three contestants answered Final Jeopardy correctly, but the outcome was already decided. 'The whole thing was like an out of body experience,' Shahade said. 'There was so much adrenaline pushing through me.' Shahade's advice to future contestants: be aggressive, but calibrate bets to your own success rate. 'If your number is 60 percent, that would change it,' he said. 'You also have to think about what your opponents’ scores are and their strength levels.' For now, Shahade returns to his life as a chess master and CrossFit enthusiast, having etched his name into Jeopardy! history.

The bottom line

• Greg Shahade ended Jamie Ding's 31-game Jeopardy! streak on Monday night, winning by $13,990.
• Shahade found all three Daily Doubles and bet aggressively, citing an 83% success rate on practice questions.
• Shahade is an International Master in chess from a family of champions; his sister Jen is a former U.S. Women's Chess Champion.
• The victory was sealed by the end of Double Jeopardy; all contestants answered Final Jeopardy correctly.
• Shahade's path to the show began with an online test in August 2024; he taped in January 2025.