Abstract The game of Gyan Chaupar or ‘Snakes and Ladders’ exists in many forms throughout history as a board game of varying size, structure, and game elements of snakes and ladders associated with various vices and virtues inscribed within the board. Three boards were analyzed via simulation in Python, including the 1998 Milton Bradley version, the 72-square Vaisnava board, and the 84-square Jaina board, with the goal of understanding the relationships between board design and associated behaviors and spiritual concepts. Game play on each board was simulated 100,000 times with variations that included individual removal of a snake or ladder, thereby quantifying the importance of that element towards achieving victory. Comparison of the weighted importance of each game element and associated vice and virtue permitted quantification of their importance for the game designer and their associated culture, with each game board component being assigned a contribution towards victory. Historical values inscribed within the class of Gyan Chaupar games were interpreted quantitatively via simulation allowing for comparison of different variations of the game and their associated cultures in different locations and time. The hypothesis that game element contribution towards victory could not be assessed by players a priori via element board length was supported by simulation data that identified many snakes and ladder game elements whose importance towards victory deviated significantly from proportionality with their game element length.