In Norman Rosten’s The Joys of Yiddish, the term “chutzpah” is defined as “gall, brazen nerve, effrontery, incredible ‘guts’; presumption-plus-arrogance such as no other word … can do justice to.” As an example of chutzpah, Rosten cites “that quality enshrined in a man who, having killed his mother and father, throws himself on the mercy of the court because he is an orphan.”

If ever a man embodied chutzpah, it was Antonio López de Santa Anna. He styled himself the “Napoleon of the West” yet was defeated in an engagement because he took a siesta and forgot to post guards in the face of the enemy. He led a rebellion in the name of freedom against a self-proclaimed emperor and then ruled as a dictator and insisted on being called “Your Serene Highness.” Having lost a leg in a farcical engagement, he insisted that it be preserved as an object of worship.

Yet Santa Anna was Mexico’s version of the unsinkable Molly Brown. Surviving defeats, disgrace and well-founded accusations of corruption, he served as president of Mexico eleven times and lived to die in bed at the age of 82. He was not without courage, was a superb organizer, and his colossal ego and reckless extravagance undoubtedly served him well in a macho society that didn’t look kindly on those imbued with puritan values of modesty and thrift. As for the numerous betrayals and doublecrosses that marked his career, they could be explained as actions of one with a finely honed sense of realpolitik.

Santa Anna was born in Jalapa, Veracruz, in 1794. Deciding on a military career, he became an infantry cadet at age sixteen. While still in his teens, he displayed valor during a campaign in Texas, where he was wounded by an Indian arrow. During the War of Independence, Santa Anna resembled Agustin de Iturbide, the man he would overthrow, in fighting on the royalist side and then switching allegiance at the last moment.

Commissioned a first lieutenant in 1812, Santa Anna was posted to a grenadier battalion whose responsibility was to protect the Veracruz-Mexico City road from rebel attacks. In 1816 he was promoted to captain. In March 1821 he was in command of a royalist detachment defending Orizaba against rebel forces led by José Miranda. Miranda urged him to come over to the insurgent side but Santa Anna made a bold sally from the city and broke the siege. On the 29th of March a large force loyal to Iturbide, who had switched sides on February 24, arrived on the scene. Seeing which way the wind was blowing, Santa Anna made the first of many betrayals that would characterize his career. Ironically, his change of allegiance coincided with a royalist promotion to lieutenant colonel for his victory over Miranda. As soon as Iturbide agreed to accept him at the rank to which he had been promoted, Santa Anna rallied to his cause.

Next it was Iturbide’s turn. The short-time emperor had made the error of wounding Santa Anna’s vanity by mildly reprimanding him for using the title Jefe Político (“Political Boss”), to which he had no right. An angry Santa Anna, who had previously made no complaints about Iturbide dissolving congress, now proclaimed himself a champion of liberty and “declared” against him. Santa Anna was lucky enough to gain the support of such true liberals as Vicente Guerrero and Iturbide was forced to abdicate in March.

In 1829 Spain rashly attempted a reconquest of Mexico. A Spanish general named Barradas landed a force of 2700 men at Tampico and a third of them promptly died of tropical diseases. Guerrero, then serving as president, sent Santa Anna to repeal the invasion. Though the exhausted and disease-plagued Spaniards were all too ready to surrender, Santa Anna announced that he had won an epic victory and found himself acclaimed the “hero of Tampico.” He became president in 1831 but promptly turned over administrative duties to his liberal vice president, Valentín Gómez Farías, and retired to his hacienda at Magna de Clavo, near Veracruz, to enjoy a round of cockfights, bullfights and other diversions. Though Santa Anna dearly loved honors and titles, he found day-to-day business of governing boring and irksome.

1836 saw Santa Anna making history in Texas. In February he led the forces that overwhelmed the Alamo; in April he was routed by Sam Houston at San Jacinto. This was the engagement in which the “Napoleon of the West” was so overconfident and careless that he neglected to post guards and was taking a siesta when Houston attacked. Santa Anna, taken prisoner by Houston, promptly signed a treaty guaranteeing the independence of Texas. Returning to Mexico in disgrace, he sulkily retired to his hacienda.

Santa Anna was down but not out. In 1838 a ludicrous skirmish took place which became known as the Pastry War. A French baker in Mexico City claimed his shop had been looted and demanded compensation from the Mexican government. He was backed up by the French government, which was trying to pressure Mexico into a trade agreement, and a bombardment of Veracruz ensued. Santa Anna, who was among the defenders, lost his right leg below the knee in the engagement. Though a body part may have been lost, honor was regained. Employing his skills at self-promotion to the hilt, Santa Anna became the “hero of Veracruz” and the San Jacinto debacle was forgotten.

On October 6, 1841, Santa Anna rode into Mexico City in a luxurious carriage drawn by four white horses and assumed power as dictator. This time he ruled in person, with his greed equaled only by his extravagance. To raise money, he exponentially raised taxes and sold phony mining shares to foreign investors. But the increased revenues were frittered away by such extravagances as outfitting a uniformed private army and giving an endless round of fiestas, most of them in his own honor. The comedy came to end in 1842 when the treasury dried up and the army was unable to collect its pay. Forced out by a rebellion, Santa Anna went into hiding in the rugged mountains of his native state. Apprehended by government troops in 1845, he was exiled to Cuba and forbidden from reentering Mexico for ten years.

But Santa Anna was harder to sink than a cork. Corresponding with U. S. President James K. Polk, he persuaded him that he was the only man who could solve the dispute over Texas. Polk, taking the bait, ordered American warships to allow safe passage for Santa Anna to land at Veracruz. No sooner had he set foot on shore than Santa Anna doublecrossed Polk and began to organize resistance against the U. S.. When war began, the president of Mexico was Santa Anna’s former vice president, Valentín Gómez Farías. Gómez Farías promptly named Santa Anna generalissimo of Mexico’s armed forces.

During the war, Santa Anna remained true to form. Using his superb organizing ability, he raised an army of 18,000 despite a depleted treasury and came within a whisker of defeating General Zachary Taylor at Buena Vista. Yet his vanity resulted in a crucial defeat against the army of Winfield Scott marching on Mexico City. Wanting to hog all the glory, Santa Anna pulled his forces out so another general would not get credit for a successful defense of the capital.

Did the disastrous U. S.-Mexican war finally write finis to Santa Anna’s career? Astonishingly, no. The conservatives came into power in January 1853 and their leader, Lucas Alamán, wanted a European prince to rule over Mexico. Until a selection could be made, Mexico would need a military dictator to keep order and Alamán felt that Santa Anna was the only figure with enough experience to do the job. In February Santa Anna again took control.

But this was the last hurrah. Alamán, the only man who could control Santa Anna, died in June. Without Alamán to restrain him, Santa again depleted the treasury with his wild extravagance.In 1854 a junta of liberals — including an up-and-coming young politico named Benito Juárez — drove him out of office and into exile.

Santa Anna attempted two political comebacks. In 1864 he returned to Mexico and tried to ingratiate himself with Maximilian by proclaiming himself a monarchist. But Maximilian, more liberal than he has been given credit for, sent him packing. He returned again in 1867, when Juárez was in power. Juárez, who had once been jailed by Santa Anna, returned the favor before again sending Santa Anna into exile.

Though Santa Anna never again regained power, he was capable of one more massive act of chutzpah. In 1874, the 79-year-old ex-dictator was permitted to return to Mexico. The first thing he did was to demand a large pension on grounds of “past services to the nation.” In refusing the petition, the government must have felt like that mythical judge who hears the appeal of the “orphan” who has killed his parents.

Santa Anna spent his last three years living on the bounty of his son-in-law.

He died on July 20, 1876.

by Jim Tuck © 2008 Published or Updated on: October 9, 2008