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The Battle of Boots and Sandals

The bloodiest gunfight in the Old West, between the Bota and Guarache political factions, happened in Laredo in 1886.

By Penelope Warren

Bullet for bullet and body for body, the bloodiest gunfight of the Old West took place not at Tombstone’s OK Corral, but in the dusty streets of post-Reconstruction Laredo. On the evening of April 7, 1886, rival political factions, the Botas and the Guaraches, shot it out in the plaza in front of San Agustín Church. Within 30 minutes, some 2,000 rounds of ammunition sprayed the square, the houses surrounding it and the assembled Botas and Guaraches. Snipers on nearby roofs joined in. So did a bright yellow “ceremonial” cannon. By the time the Buffalo Soldiers from nearby Fort McIntosh double-timed it into town to break up the fight and the gunsmoke cleared, some 16 persons lay dead. Perhaps twice as many suffered wounds. As many or more may have made their final journey — unnamed and uncounted — downstream on the currents of the Rio Grande.

A rivalry between “Boots” and “Sandals” suggests a class difference. In fact, each party included members of all social strata, from vaqueros to Laredo’s Spanish land-grant aristocrats, from Confederate heroes to entrepreneurs from France and Germany. Late-19th-century Laredo was a thoroughly international city where enterprising immigrants could come to make their fortunes and be welcomed into the community. It was no longer Don Tomas Sanchez’s sleepy villita.

For 90 years after its founding in 1755, the hamlet of Laredo was governed — first for Spain, then for Mexico — by alcaldes and cabildos drawn from the families of the first settlers who had accompanied Sanchez and been granted the original porciones of land under Spanish royal charter. The names of De la Garza, Dovalina, Benavides and Gonzalez alternate down the lists, interspersed with others of lesser prominence. When Capt. Richard A. Gillespie raised the Lone Star flag over the plaza real in 1846, claiming the land between the Nueces and the Rio Grande for the Republic of Texas, very little changed. In the 1848 elections, Alcalde Florencio Villarreal was painlessly reincarnated as Mayor Villarreal, and the cabildo rechristened as the city council. Spanish remained the language of public discourse, and the peso continued to circulate as legal tender. Of the Texan nationals Lamar brought with him, most of them transplants from the United States, many were absorbed into the social, economic and political fabric of the border community through marriage and the responsibilities of public office. Hamilton P. Bee, who had arrived in 1846 with Lamar’s Laredo Guards, remained to marry Andrea Martinez, daughter of former alcalde Andrés Martinez. He was also elected the first county clerk and eventually rose to become Speaker of the Texas House of Representatives. This pattern became the norm, so that when political hostilities broke out decades later, they were not over issues of race or culture, an immigrant upper class versus an indigenous lower class. No, they were about power, pure and simple.

Laredo voted with the rest of Texas to secede from the Union in 1861, casting its ballots 70-0 for the Confederacy. In the five years that followed, the now-booming border town became a vital point of transshipment of Southern cotton across the Rio Grande and on to the fabric mills of Europe aboard vessels immune to the Union blockade. On one occasion, Colonel Santos Benavides and his cavalry swept down on Mexican outlaw (and Union sympathizer) Juan N. Cortina, who was terrorizing Zapata County to the south. In another incident, he fought off a Union force moving upriver from Brownsville to seize 5,000 bales of cotton awaiting the ferry into Mexico. He became the stuff of legend, with his exploits reported in Texas and Richmond newspapers, and corridos sung in his honor for decades after. By the time Lee surrendered at Appomattox, the dashing colonel had acquired a political base.

But so had a less flamboyant figure. In 1852, at age 24, Raymond Martin had arrived in Laredo via France, New Orleans, Florida and San Antonio, trailing a string of failed business ventures behind him. He opened a general store east of San Agustín Plaza, became a naturalized American citizen in 1858 and was elected alderman in 1859. By 1860, he was acquiring vast acreage — some of it bought, some of it seized for defaulted loans — and the sheep to graze it. In 1870, he married into one of the city’s founding families, taking the 17-year-old Tirza García as his wife. Blessed with 10 children, they founded a dynasty that dominated Webb County politics for a century.

The post-Reconstruction Democratic Party coalesced around these two powerful men to oust Laredo’s Radical Republicans in 1872. Almost immediately, however, they split into the Benavides Party and the Martin Party. By the 1880s, Martin’s faction — characterized as “the ring” and “the Barnacles” in The Laredo Times’ pyrotechnic editorials — had gained a virtual monopoly on city and county government through the enthusiastic exercise of the spoils system and creative voting practices.

A reform movement set in, led by Benavides, the banking brothers Daniel and Patricio Milmo and a prominent Republican, J. J. Haynes. In 1884, the Reform Party adopted the lowly guarache as the emblem of its dedication to the common man. Not long after, the Martin Party began to refer to itself as the Botas, named for the footwear of the wealthy. Both parties paraded in the streets to the music of brass bands, hired extra law officers to intimidate opponents and chivvied non-citizen voters to the polls. They held meetings and demonstrations. They brandished pistols and rifles. And they drank copiously.

The Guaraches lost the 1884 elections. The rivalry grew over the next two years and, like a persistent low-grade infection, finally came to a head in April of 1886. The Botas had just won another election, and the Guaraches had just lost it. Badly. When the Botas proposed to hold a mock funeral and bury “the noble Guarache,” dead “in the flower of its age,” the parties’ confrontation turned murderous.

The election had been held April 6. April 7 dawned unseasonably cold, noisy and hung over. The political partisans who had marched and shouted and fired salvos into the night were still at it. The situation was loud enough and ugly enough that the high school on Zaragoza Street just south of San Agustín Plaza dismissed its students for the day. In a rare show of cooperation, the sheriff, a Bota, and Guarache J. J. Haynes joined forces to quiet the “half drunken mob,” but their success was only temporary.

By midmorning, a Bota wag had conceived the notion of holding a solemn funeral for the Guarache Party. The procession was set to form at Bota headquarters and proceed to the home of Guarache leader Dário Gonzalez, where a sandal would be ceremoniously interred. Announcements showing a weeping willow tree and a headstone summoned “members and associates to have the goodness to raise to the Supreme Being the prayers that their piety teaches them, for the eternal rest of the deceased.” Efforts to negotiate a stand-down failed, and at 3 p.m., the “funeral cortege” set out from Bota Hall. With banner bearers, party members, a bandwagon, some 120 riflemen on foot and 30 armed horsemen, their procession stretched for two blocks as they made their way to San Agustín Plaza. The Guaraches, who had been following their rivals with their own band and armed partisans and their yellow cannon, split off to intercept the Botas as they marched past Martin’s house and into the intersection of Zaragoza Street and St. Agustine Avenue.

No one knows who fired the first shot. Botas claimed it was a young Guarache, Francisco García. Guaraches blamed a Bota, Concepción Hererra. The Guaraches had bracketed the Botas, front and rear, but Bota snipers on nearby rooftops offset their advantage. The heaviest fighting, and most of the casualties, seems to have occurred in the first 15 minutes. Several fell at some distance from the battle. Dr. A. W. Wilcox testified that one man died in his yard, and three more within 50 feet. The dead almost included Santos Benavides’ sister-in-law, Lamar, whose husband, Cristobal, threatened to return the bullet that had missed her by inches to the man who had fired it at her — via his own pistol. Funerals went on for almost a week, eight from San Agustín alone on the day following the shootout.

The Bota-Guarache fight would have gone down in history as merely an uncommonly violent episode of a violent era, except for one paradox. The bloodshed did not lead to more bloodshed. Instead, prominent members of the two factions joined to found the Independent Club, which would ultimately become one of the most powerful and long-lived political machines in the state. Indeed, it flourished into the 1970s, when the last of the great South Texas Democratic patróns, Pepe Martin, was convicted of a single count of mail fraud and sentenced to 30 weekends in jail.

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