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Democratic citizens often revel in the crucifixion of political leaders caught lying, cheating, and stealing, leaving hypocrisy – as Shklar has argued – the only unforgivable sin. Nevertheless, hypocrisy can and often does play an essential role in democratic politics by allowing representatives to build support for policies, please diverse constituencies, and overcome political gridlock. Some of America’s most celebrated authors on effective leadership techniques advocate creative approaches to sincerity in order to more easily influence others. This paper considers the evolution of the relationship between sincerity and hypocrisy in leadership studies in American political thought. It offers an intellectual history of the way leadership texts address insincerity, with a particular aim at empowering ordinary citizens. This paper begins with America’s most famous apologist for political hypocrisy, Benjamin Franklin, who provides a guide to the art of democratic statesmanship, which includes a role for the prudent use of hypocrisy. Following Franklin's example, leadership expert Dale Carnegie extends the discussion of insincerity into the Post World War I economic era. Carnegie’s famous work, How to Win Friends and Influence People, is a populist standard that aims to empower everyday people in the pursuit of effective influence. Finally, this paper turns to contemporary debates over sincerity in public affairs. In an era of “truthiness” and #fakenews, concerns raised about leaders’ hypocrisy appear at best ineffective and at worst quaint. By uncovering the populist underpinnings of insincerity as a political tool, this study also raises the normative question of how and citizens should resist insincere expressions from political leaders in order to preserve democratic norms.