IM Greg Shahade Wins Jeopardy, Ends Ding’s 31-Game Streak

Millions of viewers of Jeopardy!—one of America’s most popular TV shows—saw a dramatic shakeup on Monday when IM Greg Shahade dethroned one of its most dominant contestants ever.

Jamie Ding had become a popular personality during his remarkable 31-game winning streak, racking up $880,000 in winnings and climbing into the top-five most successful contestants in the show’s history. Fans expected that streak to continue.

Instead, an international master from Philadelphia brought it to an end. In his introduction, Greg explained what has made him go viral on YouTube.

“I had a few videos that have over five million views, which is the good one,” he said. “The bad news is that it’s me losing in chess to nine-year-old children.”

JEOPARDY!: Interview segment (4/27/26) #Jeopardy! 📺🟦💰 pic.twitter.com/4Hew7RWwHG

— Jay (@Jay_3085) April 28, 2026

47-year-old Shahade, best known in the chess world as the founder of the league that later became Chess.com’s PRO Chess League, delivered an impressive performance. He finished with $33,000, having found all the Daily Doubles and answered each correctly to build a decisive lead. By Final Jeopardy, Shahade had more than doubled Ding’s score, sealing a runaway victory.

On the last clue of Double Jeopardy, Ding answered “palm leaf” instead of the correct “palm tree” for a question about Dubai’s man-made archipelago, dropping him to $16,000 against Shahade’s $32,600.

JEOPARDY!: Greg Shahade’s Back-to-Back DAILY DOUBLES $7,600 & $7,000 wagers (Game 1) (4/27/26) #Jeopardy! 📺🟦💰 pic.twitter.com/f0zaQLSvCz

— Jay (@Jay_3085) April 28, 2026

The Final Jeopardy clue was:

Of South Africa’s 12 official languages, these two are alphabetically first and last.

All three contestants answered correctly—Afrikaans and Zulu—but Shahade’s $400 wager sealed the win at $33,000, while Ding finished with $19,010. Third-placed Katrina Puckett finished on $4,990.

Afterward, Ding had high praise for his opponent. “He played excellently,” he said. “He did exactly what he needed to do. He made big wagers, and it was a pretty comprehensive victory.”

Ahead of the show, Greg joked about his opponent on his X account: “This is like showing up to a chess tournament, and your first round pairing is Magnus Carlsen.”

This is like showing up to a chess tournament, and your first round pairing is Magnus Carlsen.
—Greg Shahade

This is like showing up to a chess tournament and your first round pairing is Magnus Carlsen 😬

Please wish me retro good luck and I hope you have the chance to watch Jeopardy tonight!

Also no spoilers until late in the evening so everyone can watch first 😊 pic.twitter.com/VJZ9rbsCu2

— Greg Shahade (@GregShahade) April 27, 2026

While Shahade is widely known for his chess career, as a player, founder, and president of the non-profit U.S. Chess School, he has also excelled in trivia.

His sister, two-time U.S. Women’s Champion WGM Jennifer Shahade, explained in a Substack post that Greg approached trivia much like he did chess, poker, and coaching—with serious and structured training. She noted how he used repetition, building tens of thousands of flashcards across subjects from geology to pop culture, in order to sharpen his memory. Greg himself detailed the process in a 2023 post on his own Substack.

Jeopardy! is one of America’s most iconic TV shows, on the air for more than 60 years, with its modern version debuting in 1984. Hosted by legendary champion Ken Jennings, it regularly draws over eight million viewers per episode and continues to produce generations of trivia stars.

The Shahade family is no stranger to the program, with Greg writing on social media:

Jeopardy! was my mother’s favorite show; she never missed an episode. When she was alive, I wasn’t into trivia at all, so it feels really cool to have this late-blooming connection with her. Please pray for categories about my expertise: chess and donuts.

Jennifer herself was also featured on the show in 2023—presenting clues. 

Jennifer was quick to congratulate her brother. 

He did it!!! pic.twitter.com/XqeP8RIAGd

— Jennifer Shahade (@JenShahade) April 28, 2026

As the new reigning champion, Shahade continues his Jeopardy! run in Tuesday’s episode, where he will face off against Alice, a student from California, and Chris, a high-school teacher from New Jersey.