Large-language models (LLMs) are now able to produce text that is indistinguishable from human-generated content. This has fueled the development of watermarks that imprint a ``signal'' in LLM-generated text with minimal perturbation of an LLM's output. This paper provides an analysis of text watermarking in a one-shot setting. Through the lens of hypothesis testing with side information, we formulate and analyze the fundamental trade-off between watermark detection power and distortion in generated textual quality. We argue that a key component in watermark design is generating a coupling between the side information shared with the watermark detector and a random partition of the LLM vocabulary. Our analysis identifies the optimal coupling and randomization strategy under the worst-case LLM next-token distribution that satisfies a min-entropy constraint. We provide a closed-form expression of the resulting detection rate under the proposed scheme and quantify the cost in a max-min sense. Finally, we numerically compare the proposed scheme with the theoretical optimum.