The Pirates' Gambit: Inside the Bucs' chess club

July 29th, 2022

This story was excerpted from Justice delos Santos' Pirates Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

“My mindset is mostly just be in attack mode, because I know that once they begin to attack me, if I’m not ready, I’ve lost the game. So, I’ve got to start early as an attacker.”

Those words, spoken by , have, on many occasions, been used to describe pitching. He was not describing pitching. He was describing another sport, entirely: 


The Pirates have a burgeoning chess club in their clubhouse, the membership currently composed of De Los Santos,  and . That trio bring various levels of experience to the table. De Los Santos has had an interest since youth, while Underwood is an avid user of and watches Twitch streams and YouTube videos dedicated to the game.

“When I was in school, I would see a lot of kids play and compete with chess,” said De Los Santos. “I got interested in it, especially just the thought of being able to compete in a mental aspect and being able to see that this game is about being ahead of the player, making certain moves, being smart about your moves. It’s a quiet game. It’s a strategic game. Those are things that attracted me to it.”

As De Los Santos alludes, presence is required to excel in the game; success isn’t dependent on the current move, but the move that comes three, four turns down the line. The chess board is its own galaxy, and that level of immersion serves as an escape from baseball, from the real world. 

“It gets you locked in on what you have going on there,” Underwood said. “One piece can lead to the next. You could be walking yourself into a trap, or you could be beating somebody else. It’s another little cool thing I like to do and I enjoy it.”

Given his love for the game, it should come as no surprise that Underwood has seen "The Queen’s Gambit," which further inspired him to dive into the element of strategy. 

“After I did watch it, it kind of got me into reading about chess and trying to figure out how to play the game,” Underwood said. “Most of the stuff I do is self-taught. I saw that and I was like, ‘Oh, there’s openings and other stuff you can do throughout the game that you don’t think about, but if you do know, it will help you maneuver into the game a little bit smoother.’”