This essay examines letters from eighteenth and early nineteenth-century Jewish American fathers to their sons for insight into a nascent Jewish American literary patrimony. Father-son letters, whose subject matter clustered around four basic themes—family, business, civic affairs, and Jewish life—enable extended consideration of how the men of one generation sought, through a range of highly stylized and mostly derivative rhetorical performances, to influence their successors against the backdrop of historical change and adaptation to the changing conditions of North American life in the aftermath of the Revolutionary War. Notwithstanding their occasional use or invocation of a Hebrew word or phrase, these letters spoke in the language of and bore witness to the Anglo-American milieu from which they emerged. In other words, I don’t claim them as direct markers of Jewish “difference.” Nonetheless, the eagerness with which these letters relayed the writers’ strong wishes for their sons’ moral development as autonomous individuals and, at the same time, imparted firm guidance for their pursuit of familial business interests prefigures a pattern that will be familiar to readers of twentieth-century Jewish American texts. The letters offer insight into how Jewish men in the early American republic attempted to uphold familial and communal interests while negotiating the larger culture’s embrace of an individualistic ethos.