Chess is a mathmatically solvable game. Which means that, by the 23rd century, any computer should know how to win or at least force a draw in a chess game against ANY opponent. We're actually close to having computers capable of this, now.
So the answer to whom would be Trek's best chess player, assuming we're only talking about crewpersons from the hero ships, would be Data. Barclay in "The Nth Degree" might have briefly been an exception, but that would only have been based on the speed with which he could calculate his moves - the outcome of a game between Data and him would still have been inevitable math.
For all we know, Vulcan schoolchildren learn chess solutions like our children learn multiplication tables. But I doubt it, or there would have been no challenge for Spock to play Kirk. Maybe Vulcan math skills are somewhere between those of a human and a current-era PC - in which case, it is still pretty impressive that Kirk ever beat him. Maybe Spock was accepting a handicap. Or maybe Spock was also capable of mathmatically solving the game, and played specifically to allow Kirk to win sometimes as encouragement to his captain.
Another possibility is that 3D chess, unlike conventional chess, includes some element that makes it significantly less solvable - random elements like dice rolls, for example.
So the answer to whom would be Trek's best chess player, assuming we're only talking about crewpersons from the hero ships, would be Data. Barclay in "The Nth Degree" might have briefly been an exception, but that would only have been based on the speed with which he could calculate his moves - the outcome of a game between Data and him would still have been inevitable math.
For all we know, Vulcan schoolchildren learn chess solutions like our children learn multiplication tables. But I doubt it, or there would have been no challenge for Spock to play Kirk. Maybe Vulcan math skills are somewhere between those of a human and a current-era PC - in which case, it is still pretty impressive that Kirk ever beat him. Maybe Spock was accepting a handicap. Or maybe Spock was also capable of mathmatically solving the game, and played specifically to allow Kirk to win sometimes as encouragement to his captain.
Another possibility is that 3D chess, unlike conventional chess, includes some element that makes it significantly less solvable - random elements like dice rolls, for example.