Major advances in Question Answering technology were needed for IBM Watson to play Jeopardy! at championship level – the show requires rapid-fire answers to challenging natural language questions, broad general knowledge, high precision, and accurate confidence estimates. In addition, Jeopardy! features four types of decision making carrying great strategic importance: (1) Daily Double wagering; (2) Final Jeopardy wagering; (3) selecting the next square when in control of the board; (4) deciding whether to attempt to answer, i.e., “buzz in.” Using sophisticated strategies for these decisions, that properly account for the game state and future event probabilities, can significantly boost a player’s overall chances to win, when compared with simple “rule of thumb” strategies. This article presents our approach to developing Watson’s game-playing strategies, comprising development of a faithful simulation model, and then using learning and MonteCarlo methods within the simulator to optimize Watson’s strategic decision-making. After giving a detailed description of each of our game-strategy algorithms, we then focus in particular on validating the accuracy of the simulator’s predictions, and documenting performance improvements using our methods. Quantitative performance benefits are shown with respect to both simple heuristic strategies, and actual human contestant performance in historical episodes. We further extend our analysis of human play to derive a number of valuable and counterintuitive examples illustrating how human contestants may improve their performance on the show.