This article evaluates two potential interpretations of the duty to negotiate as it was addressed in the Appellate Body’s Gambling opinion, and considers whether either interpretation is reconcilable with the Appellate Body’s holdings in Turtle-Shrimp andGasoline.  Specifically, it argues that under a practical interpretation of Turtle-Shrimpand Gasoline, the duty to negotiate depends upon a finding of trade discrimination anda reasonably available less restrictive measure.  The Gambling opinion severs the necessary connection between least restrictive measures analysis, a finding of discrimination, and the duty to negotiate, and as such leads to analytical inconsistencies in the Appellate Body’s treatment of the duty to negotiate.  Indeed, not only does a closer look at Gambling lead to analytical inconsistencies, it also leads to the conclusion that (1) the Appellate Body’s holding in Turtle-Shrimp does not provide appropriate incentives for states to negotiate in good faith, and (2) the Appellate Body should reconsider its approach to Article XX GATT and Article XIV GATS by conducting a least restrictive measures inquiry under the chapeau in both “necessary” clause and “relating to” clause cases.