This article examines “courtroom paintings” in Latin American art, focusing on the works of Martín Tovar y Tovar, Juan Lovera, and especially Pedro Subercaseaux. Drawing from the philosophical work of Alain Badiou, the article offers a comparative reading of the theme of “anticipation” in several of their paintings, suggesting that this theme may point to an underlying democratic element in art about independence. The article ends by discussing Subercaseaux’s work in the context of the Argentine centenary celebration of independence, exploring the ways in which its use of “anticipation,” counterintuitively, might have made it easier for the regime to co-opt in its attempt to rewrite the moment of independence in 1910.