As the military scrutinizes and downsizes training budgets, the number of simulations for training, modeling, research, and education in the U.S. military continues to expand. The military endeavors to integrate these simulations into the military training life cycle, seeing them as essential for meeting military missions and goals in this era of reduced budgets, new military equipment, and strategies. There is little research on capitalizing on the commercial market's research and development for simulations. This study looks at one commercial simulation with a comparative analysis for the study of military history. Although this study just scratches the surface of the potential to tap into this great resource, it recognizes the limitations of current commercial simulations and the balance required in their use for historical analysis. This military history review focus is on the operational command level decisions of Operation Crusader. Operation Crusader was the desert clash between the German task force led by General Rommel and the Allied task force led by British General Auchinleck in November of 1941, using The Operational Art of War, a war game published by Talonsoft (1998). This study looks at the commercial game's use to educate military leaders to a critical analysis of examining possible command-level decisions. This study addresses this by using seven officers from different branches (infantry, armor, intelligence, engineer, aviation, quartermaster, and field artillery) who have never played The Operational Art of War, and an analysis of their experience playing the game.