We attempted to apply a novel approach to stock market predictions. The Logistic Regression machine learning algorithm (Joseph Berkson) was applied to analyze news article headlines as represented by a bag-of-words (tri-gram and single-gram) representation in an attempt to predict the trends of stock prices based on the Dow Jones Industrial Average. The results showed that a tri-gram bag led to a 49% trend accuracy, a 1% increase when compared to the single-gram representation’s accuracy of 48%.