In 1901, Sarah Orne Jewett, already famous for her local color sketches of rural Maine, boldly set out to sea, and ventured into the distant regions of historical maritime fiction, riding the waves of writers with whom she has rarely been associated—James Fenimore Cooper or Herman Melville. First published—aptly enough—in the pages of the Atlantic Monthly, The Tory Lover, her first “long story,” as she called it, is a picaresque rewriting of the American Revolution that abides by the laws of the genre and offers the reader the pleasures of fluctuating (gender and national) identities, wavering allegiances, and, more surprising in Jewett's case—if we insist on aligning her texts with the local, the minor, the micro-histories of women's lives—grandiloquent meetings with the nation's Representative Men and documented forays into war policies. “Go back to the dear country of the Pointed Firs,” Henry James famously, if somewhat derisively, intimated. And yet, Jewett, who loved nothing so much as crossing borders, was thrilled at cross-dressing as a historical romancer and was satisfied with the result. The Tory Lover has mostly—and rightly—been read as yet another example of Jewett's literary challenge to stable categories and obstinate crossing of the boundaries of genre and gender. Other borders, however, deserve consideration. The predictable fluctuations of identity, this paper argues, are worth tracking within a double historical and geopolitical context (the age of Revolution—when the story was set—and the U. S. imperialist turn of the end of the nineteenth century—when the story was written), obsessed with the possibilities of (and hindrances to) transnational flows of people, goods, culture, language, capital and the political consequences thereof. Who and what will guarantee the possibility of border-crossing, and the profits (economic, cultural, philosophical) to be gained when these borders are crossed? Indeed, the Revolutionary War, historians have recently emphasized, was a war that was fought with a view to building a state for an anticipated empire. Rewriting the American Revolution at the time when questions of national self-determination, international responsibility and expansion were once again posed to the United States on the backdrop of the “liberation” of Cuba and the Philippines, Jewett's historical romance, which she composed alongside her “imperial tales” (“The Foreigner” and “The Queen's Twin”), is better understood as an audacious intervention in the contemporary debate about the transnational dynamics of American statecraft in the context of a new empire.