When Turing considered the question, “Can machines think?” he anticipated many difficulties this claim would have to overcome before being considered seriously, much less accepted. The most basic difficulty was bias against the idea embedded in the English words machines and think. When considering this and other difficulties for his claim, Turing (1947/2004) urged that “… fair play must be given to the machine.” As Magnani (2022) points out, Turing was working at a time when the concept of computing was changing fundamentally due to the development of digital computers, in which Turing played a significant role. Turing’s ideas about thinking machines were part of his response to this profound revision in history, which both motivated and grounded his call for fair play. The aim of this article to discuss and develop Turing’s idea of fair play as a reconsideration of the trade-off between skeptical and charitable strategies for the assessment of hypotheses like machines can think. Specifically, Turing’s call amounts to the view that critics of the hypothesis are overly skeptical due to historical bias and partiality. His call for fair play is a call for a more charitable assessment of the hypothesis, one that neutralizes the prejudices embedded in his contemporary context.