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Research in two-player perfect information games have been one of the focus of computer-game related studies in the domain of artificial intelligence. However, focus on an effective search program is insufficient to give the “taste” of actual entertainment in the gaming industry. Instead of focusing on effective search algorithm, we dedicate our study in realizing the possibility of applying speculative play. However, quantifying and determining this possibility is the main challenge imposed in this study. For this purpose, the Conspiracy Number Search algorithm is considered where the maximum and minimum conspiracy numbers are recorded in the test bed of a simple Tic-Tac-Toe game application. We analyze these numbers as the measures of critical position identifier which determines the right moment for possibility of applying speculative play through operators formally defined in this article as tactic and tactic. Interesting results are obtained with convincing evidences but further works are still needed in order to prove our hypothesis.