Antonio Lopez de Santa Anna: The Man who Gambled on Revolutions.

Article by Ralph Dempsey. Edited by Cathy Humphreys. Additional Research by Ellie Veryard.

Oil painting of Santa Anna

On a sweltering Texas morning, a man was dragged out of a festering swamp wearing the tattered rags of a Mexican dragoon private’s uniform. Disorientated and almost incoherent, it was at first assumed that the man had contracted malaria, the disease so common to the area that it had become known as the soldiers’ disease. However, on closer inspection, an officer realised that the ragged deserter standing before him was none other than the Mexican revolutionary Antonio Lopez de Santa Anna; Army General and ex-Mexican President, as well as consummate gambler, compulsive womaniser and according to various accounts an opium addict who was never without his supply of opium on arduous campaigns.

The complex legacy of Santa Anna remains to this day a popular topic of both Mexican and Texas folk songs. The Mexican folk ballad La Cucaracha was modified to describe Santa Anna as the “cockroach” who could not move until he was sufficiently intoxicated. The Texas song The Yellow Rose of Texas celebrates a slave known as Emily Morgan or Emily West, who seduced Santa Anna, successfully stalling his campaign’s progress and thus aiding General Sam Houston in winning the battle of San Jacinto. The legend tells that Santa Anna’s infatuation with Emily was so strong that he failed to heed warnings about the advances of Houston’s army and subsequently had to flee to the nearby swamp to escape.

While Santa Anna does not now enjoy a distinguished legacy; in Mexico he is still vilified for his land sales which resulted in American expansion at the great expense of his native Mexico, there was a time when he was considered the “Napoleon of the west”. Romanticised by the same folk songs that would later scorn him, Santa Anna had liberated Mexico from degrading Spanish possession, before going on to drive the more corrupt and incompetent post colonial demagogues out of power in popular coups.

Battle of Churubusco 1847

This shifting reputation reflects the turbulent career that Santa Anna experienced during the age of revolutions. Like his idol Napoleon, Santa Anna rose from ignoble origins to the height of power. Indeed while Napoleon was only Emperor once, Santa Anna was President of Mexico eleven times, as well as supreme commander of Mexican military forces. Given the volatile nature of Mexican politics alongside the poor discipline and fragile command structure of the Mexican military in this period, this was a great feat, one that was never surpassed by rivals or later leaders.

However, Santa Anna also possessed the heart of a gambler, never able to resist a punt on a cockfight, (by his own estimation he spent tens of thousands of dollars cockfighting) or indeed the seduction of a dashing Senorita, (he once famously incurred the wrath of President Agustin Iturbe by attempting to seduce the President’s sister, a gamble which could have proved fatal). Never satisfied with his current status, Santa Anna always held out the hope that his next battle or campaign would enable him to realise his dreams of finally becoming the “Napoleon of the west”. To this extent he increasingly chased the gold at the end of the rainbow, losing sight of Mexican popular opinion and embarking on increasingly impulsive and dangerous schemes to win back the fickle devotion of his people.

So it came to be that Santa Anna was dragged out of that swamp in the tattered uniform of a private. Brought to General Houston’s tent, he was given a large dose of opium and spent the afternoon arranging the boundaries of the Independent Republic of Texas, no doubt in a somewhat tranquil state. Santa Anna would have done well to cut his losses here; however the great revolutionary gambler could not walk away. He briefly won back the heart of the Mexican people for the courage he demonstrated during the Franco-Mexican war. However he lost popularity again due to his inept leadership of the Mexican American war, where Mexico lost land and dignity once again to her Northern neighbour. Perhaps realising his era had come to an end, Santa Anna turned his last period of rule into a prolonged heist of government funds before fleeing into exile, travelling around the Caribbean and North America, undertaking harebrained business schemes and spending days at the cockpit. He finally finished his days at the end of a losing streak in Mexico City, a disreputable relic of another age, known only as the “cockroach” to the people he had tried so hard to impress.


Santa Anna’s alternative nickname was the Eagle.

After being hit by cannon fire, his leg was amputated and buried with full military honours. During the Mexican-American war, Santa Anna’s prosthetic cork leg was captured by the Americans. It remains on display at the Illinois State Military Museum, despite repeated requests by the Mexican government for its return.

Santa Anna’s response to Joel Roberts Poinsett, US minister to Mexico who claimed Santa Anna got what he deserved when captured in Texas:

‘Say to Mr. Poinsett that it is very true that I threw up my cap for liberty with great ardor, and perfect sincerity, but very soon found the folly of it. A hundred years to come my people will not be fit for liberty. They do not know what it is, unenlightened as they are, and under the influence of a Catholic clergy, a despotism is the proper government for them, but there is no reason why it should not be a wise and virtuous one.’

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