Antonio López de Santa Anna (b. Xalapa, February 21, 1794; d. Mexico City, June 21, 1876) was one of the most notorious military caudillos of 19th-century Mexico. He was involved in just about every major event of the early national period and served as president on six different occasions (1833–1835, 1839, 1841–1843, 1843–1844, 1846–1847, and 1853–1855). U.S. Minister Plenipotentiary Waddy Thompson during the 1840s would come to the conclusion that: “No history of his country for that period can be written without constant mention of his name.”1 For much of the 1820s to 1850s he proved immensely popular; the public celebrated him as “Liberator of Veracruz,” the “Founder of the Republic,” and the “Hero of Tampico” who repulsed a Spanish attempt to reconquer Mexico in 1829. Even though he lost his leg defending Veracruz from a French incursion in 1838, many still regarded him as the only general who would be able to save Mexico from the U.S. intervention of 1846–1848. However, Mexicans, eventually, would remember him more for his defeats than his victories. Having won the battle of the Alamo, he lost the battle of San Jacinto which resulted in Texas becoming independent from Mexico in 1836. Although he recovered from this setback, many subsequently blamed him for Mexico’s traumatic defeat in the U.S.-Mexican War, which ended with Mexico ceding half of its territory to the United States. His corruption paired with the fact that he aligned himself with competing factions at different junctures contributed to the accusation that he was an unprincipled opportunist. Moreover, because he authorized the sale of La Mesilla Valley to the United States (in present-day southern Arizona) in the 1853 Gadsden Purchase, he was labeled a vendepatrias (“fatherland-seller”). The repressive dictatorship he led donning the title of “His Serene Highness” in 1853–1855, also gave way to him being presented thereafter as a bloodthirsty tyrant, even though his previous terms in office were not dictatorial. Albeit feted as a national hero during much of his lifetime, historians have since depicted Santa Anna as a cynical turncoat, a ruthless dictator, and the traitor who lost the U.S.-Mexican War on purpose. However, recent scholarship has led to a significant revision of this interpretation. The aim of this article is to recast our understanding of Santa Anna and his legacy bearing in mind the latest findings. In the process it demonstrates how important it is to engage with the complexities of the multilayered regional and national contexts of the time in order to understand the politics of Independent Mexico.