This thesis analyzes the hypothesis that coaches in the National Football League are often too conservative in their decision making on fourth downs. I used R Studio and NFL play-by-play data to simulate actual football plays and drives according to different fourth down strategies. By measuring expected points per drive over thousands of simulated drives, we are able to evaluate the effectiveness of different fourth down strategies. This research points to a number of conclusions regarding the nature of NFL coaches on fourth downs as well as the complexity of modeling and simulating decision making in a complex sport, such as professional football. While we are able to demonstrate areas where a more aggressive fourth down strategy could be utilized to a team’s advantage, this research demonstrates that fourth down decision is not a simple binary choice and that making this critical decision must be taken in context. In other words, further research should be done that takes into account additional variables and their impact on a team’s decision to “go for it” or not on fourth down.