UPDATED STORY  (4/28/26 at 5:40 a.m. ET)

Jamie Ding has faced off against comic book writers, a The Chase competitor, attorneys, and more, but he hasn’t been challenged by a world-renowned chess player on Jeopardy! until now. Ding finally met his match on Monday, April 27, when his historic 31-day winning streak was ended by Greg Shahade, from Philadelphia, Pennsylvania.

Shahade is a big deal in the chess world, and his relationship status may raise a few eyebrows among Jeopardy! fans. He’s openly polyamorous, and seemingly has at least two romantic partners currently.

“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,” he wrote on Instagram.

Here is everything to know about Shahade:

He’s into CrossFit

Shahade exercises his body and mind. In his bio, he wrote that he is into CrossFit, which is a strength, conditioning, and overall fitness program consisting mainly of a mix of aerobic exercises, calisthenics, and weightlifting.

In an Instagram photo, the Jeopardy! player shared a photo of himself and his partner, Rae, standing in front of a mirror at the gym. Shahade wore a CrossFit shirt. “My favorite workout partner,” he wrote.

Shahade has also competed in the CrossFit Open. His Instagram profile is filled with videos of him working out.

He’s a chess master

Shahade is not only a chess player, but he is a chess master. He founded the New York Masters and U.S. Chess League, and is a former member of the board of the U.S. Chess Federation.

According to his Wikipedia page, he started playing chess at a young age and won the All-America U-13 chess cup. He has also competed in three national chess championships, tied for first place in the 1993 National Junior High School Championship and the 1996 National High School Championship, and won the 1996 United States Junior Open.

Shahade led his high school to win four National High School Chess Championships and was the top scorer in the competition. This led him to win the Samford Fellowship in 1999, which is awarded to the top chess prospects under 25. This gave the winners $25,000 to compete in and train in top tournaments.

Shahade won the fellowship again in 2000. He was named a Grandmaster in 2001, which is the highest title a chess player can earn.

His sister may be familiar to Jeopardy! fans

Greg is not the only chess prodigy in his family. His sister, Jen, is a Woman Grandmaster and is the executive editor-in-chief of the U.S. Chess Foundation website.

Jennifer has also read clues on Jeopardy! about chess, according to The Jeopardy! Fan. She is also a three-time National Chess Champion, according to her Instagram bio.

His dad, Michael, is an FIDE Master, which means he achieved an Elo rating of 2300 or more. His mother, Sally Solomon, is not involved in chess. She is an author and professor at Drexel University

He is a Ben Chan protege

Aside from his sister presenting clues on Jeopardy!, Shahade has another connection to the game show. He has trained under Ben Chan, according to AOL. Chan is a nine-day champion with all of them being runaway games. He also placed second in the 2024 Tournament of Champions. Chan gave Shahade a shoutout and a thank you during his interview in 2024.

Shahade started doing trivia in May 2021, according to his personal blog.

His job still revolves around chess

When he is not playing chess, Shahade is still involved in the chess world. In 2007, he started making chess videos on ChessVideos.tv. He has hosted over 30 sessions of the US Chess school, where young players are invited to learn under Grandmasters.

Shahade is also the host of U.S. Chess lessons, where he invites coaches to teach for future chess prodigies. He is currently the commissioner of the Professional Rapid Online Chess League.

He loves doughnuts

Despite working out all of the time, Shahade is also a huge doughnut lover. He claims that he is a “donut expert” in his Instagram bio.

In a March 2025 video, he joked that he was more than just a doughnut expert as he ate various kinds. He said he also likes to work out and travel.

His relationship status may raise eyebrows

As mentioned above, Shahane has a partner named Rae. But he also has another partner named Lydia. According to his Instagram and Twitter bios and his own blog, Shahane is proudly polyamorous.

Shahane has posted photos with both of the women in his Instagram, sometimes together, sometimes solo. For those who don’t know, polyamorous is the practice of having multiple romantic partners at the same time, with consent and knowledge from all partners.

Jeopardy!, weekdays, check local listings, stream next day on Hulu and Peacock