This paper walks the reader through a simple mathematical characterization of the popular children's game, "Chutes and Ladders," focusing primarily on Monte Carlo simulation. The focus is then shifted to the board game "No Te Enojes" in order to analyze the implications of the introduction of strategy. The presence of strategy in a game of "No Te Enojes" makes it an interesting generalization of "Chutes and Ladders." This progression allows us to explore the nature of chance in board games through the aid of computer simulation, an increasingly important topic in teaching both statistics and data science.