Throughout history, professional military officers have studied the past to learn strategic planning and decision making. While history remains the best means to study strategy, it is problematic due to imperfect knowledge of actual events and personal biases infecting hindsight. If these are some of the problems, what are solutions to using history in a more effective manner as a tool to sharpen strategic thinking? This paper examines how practitioners can develop strategy by demonstrating a methodology for constructing alternate courses of action in a historical case study. Studying options, using information known at the time and that could have been gleaned with a greater investment in intelligence, is one of the building blocks to developing a strategically analytical mind. Gaming-out options starts with identifying the enemy’s most likely and most dangerous strategic course of action. From this point one can develop a theory of victory (TOV), meaning a concept of what conditions are necessary to defeat the enemy’s strategy, such as gaining command of the sea or winning a decisive land battle. With a theory of victory, one can then develop an overall strategy, effectively a blueprint, to accomplish it. The strategy is then honed by comparison to the enemy’s most likely response. This analysis results in alternate courses of action that are in turn honed until the most efficient and effective strategy to achieve the policy objective has been determined. The goal is to implement a history-driven process that can be carried forward to developing future strategic contingencies.