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Abstract Philosophers have spent a great deal of time debating whether intransitive preferences can be rational. I present a risky decision that poses a challenge for the defender of intransitivity. The defender of intransitivity faces a trilemma and must either: (i) reject the rationality of intransitive preferences, (ii) deny State‐wise Dominance, or (iii) accept the bizarre verdict that you can be required to pay to relabel the tickets of a fair lottery. If we take the first horn, then we have a synchronic refutation of intransitivity, an improvement on widely criticized diachronic arguments. I sketch possible responses that may rescue intransitivity and argue that each response is possible but generates an explanatory debt. I conclude by showing how the challenge here clarifies the foundations of decision theory without transitivity, conditional on some explanatory debt being payable.
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