One type of machine learning, text classification, is now regularly applied in the legal matters involving voluminous document populations because it can reduce the time and expense associated with the review of those documents. One form of machine learning - Active Learning - has drawn attention from the legal community because it offers the potential to make the machine learning process even more effective. Active Learning, applied to legal documents, is considered a new technology in the legal domain and is continuously applied to all documents in a legal matter until an insignificant number of relevant documents are left for review. This implementation is slightly different than traditional implementations of Active Learning where the process stops once achieving acceptable model performance. The purpose of this paper is twofold: (i) to question whether Active Learning actually is a superior learning methodology and (ii) to highlight the ways that Active Learning can be most effectively applied to real legal industry data. Unlike other studies, our experiments were performed against large data sets taken from recent, real-world legal matters covering a variety of areas. We conclude that, although these experiments show the Active Learning strategy popularly used in legal document review can quickly identify informative training documents, it becomes less effective over time. In particular, our findings suggest this most popular form of Active Learning in the legal arena, where the highest-scoring documents are selected as training examples, is in fact not the most efficient approach in most instances. Ultimately, a different Active Learning strategy may be best suited to initiate the predictive modeling process but not to continue through the entire document review.