A Greenwich third grader has dreams of one day becoming a chess grand master. Having learned to play in pre-school, Jackson Hickey, 9, might just be on the right track.
Of course it was Bobby Fischer who famously said “Chess is life,” but Jackson is learning that like life, chess takes strategy, patience, resilience and learning from mistakes.
Jackson Hickey shares some of his trophies. March 10, 2026 Photo: Leslie Yager
At home, Jackson’s awards shelf includes a first place trophy from the Connecticut State Grade Chess Championship, a competition hosted by the National Scholastic Chess Foundation that was held at GCDS earlier this month.
With his early start and growing skill set, the sky’s the limit for the Brunswick third grader who learned to play alongside his father, Brett.
“The only problem is he got better than me,” Brett said.
“He plays on chess.com every morning before school and that’s been the source of his biggest growth,” Jackson’s mother Allison shared. “It’s like a video game but for your brain.”
“I first learned with my dad,” Jackson said. “We started playing just as a game because my dad gave me a set of board games.”
Allison said No Stress Chess, a beginner-friendly, educational board game, helped start Jackson’s chess learning curve.
Jackson said he has been able to apply his chess strategizing to sports where he anticipates an opponent’s moves. That, he said, has paid off on the ice for hockey, on the squash court and in the pool at the YMCA Greenwich for water polo.
“For squash, when someone hits the ball, I remember where they are so I can hit it away from them and make it harder for them to get,” Jackson explained. “And in hockey, I think, what did the goalie do before – what is he good at or bad at. And should I hit it high or low, or try to juke him out.”
Allison said Jackson’s strategic thinking carried over to a Noetic math competition this year. The competition is nationwide and Jackson competed for Brunswick and won.
Jackson Hickey at home in Greenwich. March 10, 2026 Photo: Leslie Yager
Allison and Brett, who described their son as a typical energetic boy, said chess provides a nice transition to slow down after physical activity and vice versa.
For example, Allison said while Jackson is competitive and likes to win, when he plays in tournaments at DIG Chess in Weston, the players pivot to dodgeball between games of chess.
“It helped him learn not to take chess so intensely,” Allison said.
From a parenting angle, Brett said Jackson has learned to understand the value of sleep, hydration and nutrition as they are key to preparing for a long tournament and are interrelated.
Jackson Hickey at home in Greenwich. March 10, 2026 Photo: Leslie Yager
Today Jackson is on both the DIG Chess travel chess team and the Brunswick School team.
“I love to play chess with my friends. When we lose a game we study it, and review,” Jackson said, going on to describe a moment in a recent tournament. “In one game there was a kid from my chess team. He had three seconds left and moved so quickly. Then I checkmated him when he had one second left. It was so intense! Also because he was a friend.”
Allison said, “We use chess for life learning – and to talk about if you have a feeling emotionally. For example, if a player puts you in a tough position, you don’t do the first thing that comes to mind. You stop and consider all your options, and then decide how to act.”
Brett said when he was growing up, his father was a school teacher and role model.
“I realized afterward, the things he did became my normal,” he recalled. “We’re teaching our kids norms as well – not just celebrating the sports, though it’s important for an energetic boy who likes physical sports. But we want well rounded people.”
To that end, Jackson enjoys his spot on the 10U Water Polo travel team through the Greenwich YMCA where Brett is on the Board of Directors and Allison is on the Parenting and Family Committee.
Jackson is also part of the Singing Bruins, Brunswick lower school’s choral group and is an avid reader and fan of Stuart Gibbs FunJungle series.
Brett and Allison say they support the YMCA Greenwich in particular because it offers sports and enrichment opportunities for the entire community, especially the children.
“There’s swimming lessons and different sports after school – and everything from coding to STEM to piano for kids,” Brett said. “It’s important to have all the children in town supported.”
Find information about the YMCA Greenwich including summer camp registration online.