Philly Chess Master Talks Defeating Jamie Ding on Jeopardy!

Philadelphia chess master Greg Shahade, who defeated Jamie Ding on Jeopardy on Monday night / Photograph courtesy of ABC/Jeopardy

The Flyers lost on Monday night, yes. But Philadelphia still scored a major win, with Rittenhouse Square resident Greg Shahade ending Jamie Ding’s 31-game winning streak on Jeopardy!. Shahade didn’t just beat Ding. He beat him by $13,990. We caught up with Shahade right after the match, which he watched at the home of his sister Jen Shahade, professional poker player, chess wiz, and author of the new book Thinking Sideways: How to Think Like a Chess Player and Win at Life. (Smart family.)

Congratulations on your big win. How are you celebrating?
We had a bunch of people over, and now my nephew is excitedly watching the Flyers game, so I had to move to a quieter place.

I love that you just won Jeopardy!, defeating Jamie Ding, who had close to $900,000 in winnings, and instead of having dinner at Parc, you’re watching the Flyers game.
I didn’t say I was watching it. He is watching it.

Got it. What was your process getting onto Jeopardy!?
I got into trivia late in life, like a few years ago. I took the online Jeopardy! test a few times, and the first time they invited me to do a second test was in August 2024. I took the second test. Then they invited me to do an interview-type thing. They already know at that point that you know trivia, but they also need to know if you would make a good cast member. They want to make sure that you can speak in a reasonable manner. And they want to know what you’re into, what your interests are. And then in January, they invited me to be on the show.

And aside from trivia, what are your interests?
Well, I’m an International Master at chess, which is one level under Grandmaster. I come from a chess family. My sister won the U.S. Women’s Championship of Chess a few times, and my dad is a four-time Pennsylvania state chess champion. And I’m really into CrossFit. I go to CrossFit OBA on Washington Aveue and Orangetheory in Center City.

What’s it actually like the day of the taping?
They tape five shows in a day, and when you get there, you don’t know if you’re gonna play the first game of the day or what. I think they draw names out of a hat. It’s randomly decided. And I got drawn for the first game. You do a practice round so everybody can get used to the buzzer, and if you’re not good at the buzzer for some reason, they will tell you what you are doing wrong. I had no issues with the buzzer, but I was very, very nervous.

And when you saw the categories, was there one that made you particularly nervous?
Not really. I knew that I’d be better at some categories than others. Like, there was a fashion category. I wasn’t very good at that, but then you still have five other categories out there in each round. And even if you’re not good at a certain category, sometimes you still get the answers right anyway.

What does it take to be successful on Jeopardy!?
It’s a tough question. There’s so much that goes into it. And this game could have been different. Like, there’s an alternate universe where I show up and get totally crushed. That could have happened. But you have to play a lot of practice games online. You have to study a lot of old Jeopardy! matches. And then betting strategy is huge. You have to be a little aggressive with your bets, and it also helps if you can find those Daily Doubles. I found all three.

Greg Shahade and family members right after his Jeopardy! win

And you made some very big bets on them, which made me nervous.
I knew I was going to go all in. It wasn’t a close decision, because in my training, I get the Daily Doubles right about 83 percent of the time, which is a very high number. So I really needed to bet on myself and just hope that the question is one that I know. And the one — the one about Oscar Wilde — I knew what it was but I just couldn’t get the name of the play out. I was really panicked. Time was running out, and I was just going through every single Oscar Wilde play in my head and just before time ran out came up with, “What is Lady Windermere’s Fan?” And, fortunately, I was right.

What’s your advice on betting for future contestants?
Well, it depends on how often you get the questions right in training. Me, I’m at 83 percent. But if your number is 60 percent, that would change it. You also have to think about what your opponents’ scores are and their strength levels. I know that Jamie is very, very, very good, so I wanna be aggressive and just take my shot, whereas let’s say I’m playing somebody where I am just much, much better than them, I might not want to risk it. But overall, you should be pretty aggressive.

The Double Jeopardy round was a real nail-biter. You had quite the lead over Jamie, but he was slowly catching up. But then you ended the round with just more than double his money, meaning it was all over unless you did something outrageously stupid with your Final Jeopardy bet.
Right, and it turns out that we all got Final Jeopardy right, but it didn’t matter at that point. The whole thing was like an out of body experience. There was so much adrenaline pushing through me.

What were your interactions with Jamie like before the match? Was he trying to psych you out?
No, no. He is like the sweetest person — really, really nice. Before the match, I did hype myself up a bit. Hit my chest a little bit, just kind of like to get pumped.

And after?
He said some really nice things. And when I got back to the green room, where all the other contestants for the day are, everybody was applauding. I guess because it was a good game but also because they were probably happy not to have to face a 31-day champion. And then they moved me to the champion’s dressing room — you get your own dressing room once you win. And then, you’re right back out there playing again in 20 minutes. You just had one of the biggest moments of your life, and then they throw me right back out there.

Getting back to the betting, are you a poker player like Jen?
No, no. I used to be a professional poker player, but I basically stopped in 2011 after Black Friday. Then I taught Jen some things, and now she’s a professional poker player.

So should I bet on you winning again tonight? I know you can’t tell me, but what’s going to happen?
All I will say is that I’m playing two very nice people on Tuesday night. [Laughs]