This study investigates the impact of chess personalities on game outcomes. To this end, the author utilizes two virtual chess grandmasters, Nimzowitsch and Fine, and three class-C players who vary in their chess personalities. Chess personality is defined as the style of a chess player during their games against other players in the community. The present study analyzed the Chessmaster agreement percentages on moves made by class-C players while competing against Nimzowitsch and Fine. Specifically, Cole and Ginger demonstrated superior performance compared to Kanna, which highlights the influence of player personality and grandmaster color on game outcomes. Additionally, consistent with previous research in this area, players performed better when competing against Fine than Nimzowitsch. The results were analyzed through the lens of cognitive load theory and social cognitive theory. These findings underscore the importance of understanding individual player characteristics and contextual factors in shaping dynamics and strategic decision-making in chess. Such insights can be valuable in the development of tailored training programs and in helping businesses formulate effective strategies.