This paper seeks to reorient the focus of conflict and change in the mid-nineteenth century. Rather than examining these conflicts through Atlantic-oriented lenses, this paper sets it sights across the mountains to Chile and the Pacific Ocean. There, this paper finds a different, previously underappreciated set of stakes and causes to the intense political conflicts in western Argentina. Using the 1866-67 Revolución de los Colorados and a reimagining of the classic figure of the caudillo, this paper explains this rebellion as a product of the opportunities and uncertainties surrounding copper mining in northern Chile and the trans-Andean commercial connections it engendered by tracing the history of one of the rebellion’s Chilean financers. By understanding this financer through the lens of caudillismo, the paper ultimately suggests that rather than seeing the caudillo and western Argentina as parts of a story of receding and outdated political ideas and movements, we ought to understand these figures and places also as harbingers of a liberal, capitalist future.