Could a troupe of monkeys really produce Shakespeare if allowed to bang away at the word processor long enough? This age old question, commonly referred to as the Eddington problem, relates to fundamental issues of probability, and is examined in this article in a new light. Based on earlier research by the physicist William Bennett, Jr., the author describes a data structure which enables the computer to simulate the hypothetical monkeys. Exploiting principles of cryptology, the computer leads the simulated monkeys closer to their goal. Though the intent of the article is to encourage humanistic speculation, the final result proves to be quite practical and may come as a surprise to computer scientists and humanists alike.