Most red-blooded Americans probably only think of Generalissimo Antonio de Padua María Severino López de Santa Anna y Pérez de Lebrón as being the mustache-twirling bad guy in all the Alamo movies, but the real-life Santa Anna is probably one of the weirdest and most fascinating men who ever lived. A brutal tyrant, beloved war hero, and a Presidente-por-Vida who was far more interested in betting on cockfights and banging tavern girls than he was in managing the day-to-day operations of his government, the “Napoleon of the West” is a guy who spent most of his life rail-sliding a roller coaster track of up-and-down military and political success. He fought more battles than Napoleon and George Washington combined, yet he lost pretty much all of them. He gained independence from Spain and acquired a half-million miles of territory for the country of Mexico, then lost twice that in failed wars and bad political decisions. He was a hero of the Mexican people, elected to the Presidency no fewer than eleven different times, and yet he was also a horribly ruthless dictator who was stripped of power and exiled from his homeland on at least a half-dozen occasions. He rocked a prosthetic leg, was almost single-handedly responsible for bringing bubble gum to the United States, has a sea shanty named after him, once led a military coup against himself, and kind of looks like the bad guy from No Country for Old Men. Despite all this, when you really get down to it, Santa Anna’s history IS the history of Mexico in the 19th century.
That alone should probably qualify him as a badass, but just wait until you get a load of this shit.
Antonio Lopez de Santa Anna was born outside Vera Cruz on February 21, 1794, at a time when Spain was still ruling Mexico as a colony. Even though his middle-class parents wanted him to be a merchant, Santa Anna defied their wishes and joined the army at the age of 16. Fighting in the Veracruz Infantry Regiment, Santa Anna battled a brutal war against Native American uprisings and the guerilla beginnings of what would become the Mexican Revolution. Riding the countryside under the famously-brutal Spanish officer Joaquín de Arredondo, Santa Anna quickly proved himself as a hardcore pipe-hittin’ badass. He took an arrow to the arm in 1811, and was cited for bravery at the Battle of Medina in 1813, when Colonel Santa Anna rode down a force of Texas and Mexican rebels, killing 1300 of the enemy while only losing 55 of his own men.
Santa Anna fought hard and brutal battles alongside the Royalist Spanish government in the early days of the Mexican War of Independence, but as the war progressed Santa Anna changed his mind and threw his military support behind a rebel named Agustín de Iturbide. Winning many battles against the Spanish Royalists, Santa Anna helped win Mexican Independence and drive the Spanish out of the country. Then, when Iturbide turned out to be a douchebag, Santa Anna changed sides again, joined a rebel group, and overthrew Iturbide in 1823. Then in 1828 he fought a war that overthrew that guy as well.
It didn’t take Santa Anna long to earn a reputation for being a hardcore warrior you didn’t want to fuck with, but also who you really couldn’t trust not to shank you in the ass the moment the war started turning bad against you.
In 1829 the Spanish King returned to Mexico with the intention of beating the rebel country back into submission. As the most experienced and most successful military commander in the country, Santa Anna was called forth to lead the Mexicans in the resistance. At the Battle of Tampico in 1829, he bravely led a rag-tag group of Mexican guerillas in a defensive action that fought back an entire Spanish fleet in a single day. The “Hero of Tampico” earned so much fame and glory from this victory that in 1833 he was overwhelmingly elected President of Mexico.
Santa Anna was thrilled to have the power and honor of being president, but he couldn’t have given half a shit about the boring details of actually running a country. He basically handed over the reins of his government to his Vice President almost immediately, and spent the next two years gambling on cockfights and fathering a bunch of illegitimate children. When the VP pissed everyone in Mexico off with his stupid political decisions, Santa Anna brought an army to Mexico City and fucking overthrew his own vice president with a military coup against his own government. How fucking awesome is that?
"Now I'M in charge around here...
Ok, well in 1836 the people of Texas got sick of this political instability bullshit and launched a revolution to break away from Mexico and become the independent Republic of Texas. This really really fucking pissed Santa Anna off. He declared all Texas rebels who dared stand against him would be treated as pirates and murderers, and not be given the honor of being treated as soldiers. Sure, this is super not cool, but you have to kind of give this guy a head nod for the no-fucking-holds-barred scorched-earth Genghis Kahn shit this motherfucker put into the war effort. He marched his men across Texas leaving a smoking crater of burned crops, dead livestock, and brutally-executed prisoners in his path. After straight-up murdering POWs in the Goliad Massacre, Santa Anna continued on and wiped out Texas forces at The Alamo, killing Davy Crockett, Jim Bowie, William Travis, and every other defender to the last man in the process.
In the end, however, Santa Anna’s brutality only made the people of Texas really fucking pissed off, and at the Battle of San Jacinto they beat the shit out of Santa Anna so fucking hard that “Remember the Alamo” and “Don’t Mess with Texas” became part of the American vernacular. Texas commander Sam Houston curbstomped Santa Anna’s forces, destroying the entire Mexican Army at the cost of just 11 Texan lives.
But Santa Anna was awesomely fucking arrogant even to the last. When brought before Sam Houston as a prisoner of war, Santa Anna stood tall, looked his enemy in the eye, and said (in perfect English) "Sir, yours is no common destiny; you have captured the Napoleon of the west."
Since Santa Anna was the current President of Mexico, he couldn’t really be executed for his crimes, and instead Sam Houston sent Santa Anna to Washington DC to negotiate a peace treaty. Santa Anna went to the U.S. capital, hung out with Andy Jackson, and straight-up made a peace treaty with Texas and the United States without even so much as consulting the Mexican Congress. After signing the deal, Santa Anna went home to find that while he was fucking around the States he’d been deposed and exiled from Mexico.
Of course, Congress called him back a few months later to put down a rebellion in the state of Zacetetas. Santa Anna showed up, marched his army to the walls of the capital, told the people of the town he would gracefully negotiate with them, and then when they came out to talk he opened fire, stormed the gates, and sacked the city Attila the Hun style. This action got him exiled once again.
Santa Anna was called out of retirement just one year later, when the French Army launched an attack on the city of Vera Cruz in 1838. Racing to the battle, Santa Anna led his men in a desperate defense of the city against a French invasion fleet, commanding his fort’s defenses and leading men in street-to-street fighting all throughout the city. Santa Anna was so close to the front that his horse was killed with a bullet, so he changed horses, rode back, and then took a blast of cannon grapeshot that blew off the lower part of his leg and killed his horse again. He’d wear a prosthetic leg for the rest of his life, and in 1841 he would give his blown-off leg a full military parade through the streets of Mexico City before setting it out on public display for all to see.
Santa Anna lost the battle and the city of Vera Cruz, but he had fought bravely, and with very little in terms of trained forces at his disposal. The French invasion force signed a peace treaty with Mexico immediately following the fight, and his success and personal heroism in the battle got Santa Anna appointed Dictator of Mexico almost immediately after.
Well, as we’ve seen, this guy was super charismatic, well-spoken, and probably a shitload of fun to hang out with, but as we’ve already seen he wasn’t a great head-of-state. He was voted out of office in July of 1839, re-elected in 1841, and then exiled again in 1845.
Santa Anna was chilling in Cuba when 1848 when he heard the news that War was brewing between Mexico and the United States. The exiled General immediately headed to Washington DC and offered his services to American President James K. Polk, asking Polk for the opportunity to travel to Mexico City and help broker peace between Mexico and the U.S. Polk agreed, sent Santa Anna to Mexico, and the moment he got there he immediately was given full command of the Mexican Army and prepared for a full-scale war with the United States.
As you’d expect, he got his ass whomped. Again. Like, he was beat so hard that his prosthetic leg was captured by the 4th Illinois Infantry and brought back to the States. It’s still on display at the Illinois State Military Museum in Springfield.
It shouldn’t surprise you at this point to hear that SANTA ANNA STILL WASN’T DONE BEING PRESIDENT OF MEXICO. He was exiled to Jamaica, sure, but then they of course brought him back to be President of Mexico for the motherfucking eleventh time. This reign lasted until 1855, when Santa Anna sold New Mexico and Arizona to the United States to pay off some of his debts. This got him exiled for the final time, although he did doggedly spend the rest of his life trying to get back and rule for a twelfth time. One particularly-hilarious instance of this came when the French invaded and conquered Mexico in 1863 (the Cinco de Mayo battle happened during this time period). With the Mexican people calling out for aid, Santa Anna nobly approached the United States and offered his services in leading a force to re-take Mexico and throw out the French invaders. He conveniently failed to mention to Abraham Lincoln that Santa Anna had also sent a secret letter to the French offering his services to help keep the Mexicans subjugated under French rule.
As a bizarre footnote of history, while Santa Anna was hanging out on Staten Island in 1863 he ran into an inventor named Thomas Adams. Adams was all like, “yo dude what’s that stuff you’re chewing on?” and Santa Anna told him it was a substance called chicle that was derived from the Mexican sapodilla tree. Adams bought some of the chicle off of Santa Anna, added flavored sweetener to it, called it Chiclets, and made a shitload of money. He later teamed up with William Wrigley Jr. to create the largest chewing gum company in the world. Come to think of it, this might be Santa Anna’s most successful achievement.
Despite ruling the country with an iron fist, selling off huge chunks of the reason, and losing several wars, Santa Anna was finally pardoned and allowed to return to Mexico in 1874. An old man, half-blind from cataracts, Santa Anna settled down in Mexico City and died in the country he loved in 1876. He given a full military burial with honors, and was buried in Mexico City in a glass coffin – an incredibly high honor.
Ok, so, sure, Santa Anna was a brutal guy who double-crossed his friends, took no prisoners, and pretty much failed at everything he tried to do. But, in my long history of writing this website I’ve always defined badassitude not by the nobility of a man’s cause, nor by his success in achieving his goals, but rather by the sheer fucking determination he displays to achieve it. And, when you measure things like that, it’s hard to not consider Antonio Lopez de Santa Anna to be deserving of the adjective.
“However he may have been condemned by parties,
his career formed a brilliant and important portion of the History of Mexico,
and future historians will differ in their judgment of his merits.
General Santa Anna outlived his usefulness and ambition,
and died at the ripe age of eighty-four. Peace to his ashes"
--Obituary Mexico City 1876