Yes, it is highly probable that pirates played chess. While definitive historical documentation is scarce, the overwhelming circumstantial evidence strongly suggests that pirates of the Pirate Age engaged in games of strategy like chess. They used to refer to board games generally as 'tables,' a wider term for all board games played for
gambling and entertainment to combat the intense boredom of long voyages at sea.
Chess is obviously a harder one compared to, say, dice. However, by the time of the Caribbean Pirates, roughly the mid 17th to early 18th century, the modern chess had been established in Europe for a couple of centuries. It was played by the gentry (and there was a surprisingly high number of rich and noble men among the pirate community), also by a rising middle class, and was known across many parts of the globe where sailors and merchants traveled.
Another reason to support the idea is cultural, and it's gambling. Considering the mindset of treasure hunters, they loved gambling. In the 17th century, chess was often associated with gambling —
often for serious sums of money, which gave it a somewhat shady character in some quarters. Unlike the modern world's position of chess as a purely skill-based and prestigious game, the game's 'gambling nature' in the Pirate Age made it a perfect fit for their typical culture, which was heavily focused on risk and immediate gain.
After all,
Chess as a wargame requires strategic thinking and calculation—qualities that a pirate captain and their crew certainly valued in their line of work!
There may not be a document saying,
"Blackbeard played a game of chess against Bartholomew Roberts on August 14, 1718." However, given that chess was a common European game, that pirates were often rebellious sailors looking for all forms of recreation, and that the game fit their risk-taking culture, it's safe to say that pirates played chess, alongside cards and dice. Many skippers and yacht owners of the modern day carry chess sets on their boats.