Daryl Morey teams up with Philly-born chess master Jennifer Shahade at Rittenhouse Chess Club’s charity tournament

There were two kinds of GMs on hand at Rittenhouse Chess’ charity tournament at Queen and Rook Game Cafe on Sunday afternoon.

Former Sixers president of basketball operations Daryl Morey and Philly-born Woman Grandmaster Jennifer Shahade both attended the event, which drew 64 players from across the city.

Despite parting ways with the Sixers after the team was swept in the Eastern Conference semifinals by the Knicks, Morey kept his promise to show up for Rittenhouse Chess Club’s Charity Blitz Tournament.

» READ MORE: Daryl Morey made some poor decisions, but was he simply a victim of the Sixers’ circumstances?

“[It is] very cool of him to still come here after not being with the Sixers,” Zach Pepsin, one of the event’s organizers, said. “He definitely loves chess, and it’s a cool thing to do for charity.”

Pepsin said through the tournament’s $30 entrance fee and raffle, Rittenhouse Chess will able to donate more than 100 chess boards to local organizations, including the Children’s Hospital of Philadelphia, the Ronald McDonald House and After School Activities Partnerships, among others.

Pepsin, a 32-year-old software designer, has been an active member of Rittenhouse Chess since it started in 2021. The club, which meets twice a week, on Wednesday and Sunday in Rittenhouse Square, runs occasional tournaments, including one in February at Brauhaus Schmitz.

Pepsin was not organizing that tournament, but he asked to see the list of entrants to see which of his friends he could expect to see. Instead, Pepsin spotted Morey’s name among the registered players.

“No one else who runs Rittenhouse has any idea who Daryl Morey is,” Pepsin said. “I’m a huge Sixers’ fan. I’ve had season tickets for over 10 years now. When I saw his name, I thought it was a joke. I was like, ‘Oh, who put his name on here?’ They had no idea who he was. It turned out it was real, and he just wanted to play some chess.”

Morey missed out on the tournament in February, as the Sixers were in the midst of a three-game road trip, but for Pepsin, the executive’s sign-up was kismet. Pepsin was planning to reach out to Morey, whose love for chess is documented through interviews and a bot on chess.com, to see if Morey would be interested in helping Rittenhouse with a charity event after basketball season.

Pepsin reached out to Morey in spring, and the executive agreed to come for the club’s tournament in June. There were concerns among the organizers that Morey’s dismissal from the Sixers would change his plans for the summer, but Morey remained committed to the tournament.

Morey declined to speak with media at the event, but he found his way to Queen and Rook as the tournament was entering its final round.

He played alongside Shahade in a “hand and brain” team game against two of the tournament’s top performers. Shahade, playing as the brain, told Morey which piece to move, while Morey, the hand, had to decide where to move the piece Shahade selected. Morey and Shahade lost the match after their 10-minute timer ran out.

Shahade and Morey are friends, having met at Massachusetts Institute of Technology’s Sloan Sports Analytics Conference. Shahade, who became a Woman Grandmaster in 2005, has attended the conference each year since 2021 and has spoken at the conference multiple times about chess and poker, which she also plays professionally.

“I’ve known [Morey] for a long time,” Shahade said. “He’s a pretty good chess player. He’s especially good with strategy.”

Shahade, who drops into Rittenhouse Chess meetups monthly, also played in a simultaneous exhibition against five players at once. The players were selected as part of the raffle, which also included five copies of Shahade’s latest book, Thinking Sideways. Shahade beat four of her opponents in the timed exhibition.

Shahade said seeing organized tournaments and club meetings across the city is a testament to the game’s ability to bring people together in a time where isolation is becoming more common.

“Ever since the pandemic, there’s been a huge hunger [for chess],” Shahade said. “But there’s also been hunger around board games in general, churches, synagogues. There’s real interest in people getting offline and meeting each other in real life. I think you see that in chess.”

Shahade said she expects the interest around chess and other face-to-face games to increase as the role of artificial intelligence expands in people’s daily lives.

“Now, not only are you not necessarily talking to someone you might be friends with, you’re probably not even talking to a person at all,” Shahade said. “I think that’s just making people crave the real life interactions even more.”

Andrew Graham, 31, started Rittenhouse Chess in 2021 to try and meet new people in a new city. Graham moved to Philadelphia from Cheyenne, Wyo.

“I didn’t know anybody,” Graham, who works as a data scientist for PECO, said. “I wasn’t that into chess, but I needed activities to meet people. So, I picked chess.”

Graham looked for a preexisting chess club, but the city’s most prominent club, the Franklin-Mercantile Chess Club, closed during the pandemic. So Graham set out to start his own club, bringing a board with him to Rittenhouse Square and waiting for passersby to come over and play.

“I started making friends, and some people started to return,” Graham said. “Slowly, it picks up, and then over the course of two months it picked up pretty good.”

Sarah Court, a 27-year-old freelance artist, claims to be the club’s second member, as she walked up and played Graham in the club’s early days.

“It was just Andrew out there, and I walked out and played with him,” Court said.

Court, who does artwork for the club’s social media and merchandise, helped run the tournament on Sunday.

Now, a handful of people come together every Wednesday and Sunday to play in Rittenhouse Square, one person on each side of the wall that surrounds the center of the square.

Roughly 100 people came to Sunday’s tournament, and the 64 players came from the vibrant chess community around the city, including players from South Philly Chess and Capitolo Chess Club, among others.