In this paper are discussed recent efforts to provide preservice mathematics teachers with opportunities to connect elementary teaching methods and content with the content and methods of secondary school mathematics. Through an in-depth exploration of the game, Shut the Box, preservice elementary and secondary mathematics teachers thoughtfully analyzed and manipulated computer-generated output, developed and tested their own conjectures, and collaboratively answered questions involving theoretical probabilities "across courses and content levels". Through their collaboration, the preservice teachers gained a better appreciation of mathematics content and pedagogical strategies that lie beyond the grades they will likely teach, as they reconsidered the importance of content and pedagogical knowledge at every level of mathematics instruction. These interactions are considered in this document through a discussion of the mathematical underpinnings of the popular board game.