This piece is a chapter in the book Discussions in Dispute Resolution: The Foundational Articles (Oxford University Press, 2021). The piece comments on Professor James White’s foundational 1980 article, Machiavelli and the Bar: Ethical Limitations on Lying in Negotiation. The comment hones in on how Professor White’s seminal piece likely influenced the drafting of Model Rule 4.1, dealing with a lawyer’s obligation for being “truthful” in negotiations. Specifically, Professor White made insightful arguments regarding when and why lawyer-negotiators must be allowed “some deviation from truthfulness.” He argued convincingly as to why not allowing such deviation could interfere with a lawyer’s ability to zealously represent a client, or to achieve optimal settlement results. In suggesting that the Model Rules include limited situations for less-than-complete truth-telling, Professor White demonstrated keen awareness that creating effective ethics rules for negotiation was not simply a matter of producing a perfect draft; rather, White’s article effectively anticipated the obstacles that any draft language would face along the road to being adopted and, ultimately, enforced. Professor White’s piece remains vibrant today not only for his understanding of the legal ideas and principles involved in shaping the rules, but also for his insight into the role that human nature and politics would play in the ability of those rules to survive and thrive in the long run.