A recent trend among sports fans along both sides of the letterman jacket is that of Daily Fantasy Sports (DFS). The DFS industry has been under legal scrutiny recently, due to the view that daily sports data is too random to make its prediction skillful. Therefore, a common view is that it constitutes online gambling. This thesis proves that DFS, as it pertains to Baseball, is significantly more predictable than random chance, and thus does not constitute gambling. We propose a system which generates daily lists of lineups for Fanduel Daily Fantasy Baseball contests. The system consists of two components: one for predicting player scores for every player on a given day, and one for generating lists of the best combinations of players (lineups) using the predicted player scores. The player score prediction component makes use of deep neural network models, including a Long Short-Term Memory recurrent neural network, to model daily player performance over the 2016 and 2017 MLB seasons. Our results indicate this to be a useful prediction tool, even when not paired with the lineup generation component of our system. We build off of previous work to develop two models for lineup generation, one completely novel, dependent on a set of player predictions. Our evaluations show that these lineup generation models paired with player predictions are significantly better than random, and analysis shows insights into key aspects of the lineup generation process.