Literally translated as “tequila people,” tequileros were smugglers who transported tequila illegally from Mexico into the United States for profit during the United States Prohibition era (1920–33). They typically operated through rural South Texas and navigated back trails and made use of low-water crossings along the Rio Grande. These smugglers were usually male, ethnic Mexican, and often used donkeys and horses to transport their liquor. Tequileros enjoyed a period of success but were driven out of business before the end of Prohibition by Texas Rangers and U. S. Customs inspectors, with whom contact often ended violently.
Tequilero operations were simple, clever, and effective. They often operated at night in groups of three to five individuals. Mexican nationals tended to work on the supply side of the operations and relied on Tejanos (Texas-born Mexican Americans) as guides, support, and go-betweens, with Anglo bootleggers who then worked distribution. Tequileros proved adept at packing their draft animals and used them expertly. Horses usually carried the smugglers, while mules and donkeys carried contraband. A skilled packer could fit fifty or more protectively-wrapped bottles on a mature mule or donkey. Layers of hay or grass helped prevent bottles from breaking and, with the twine bags that carried them, muffled the telltale clanking of glass. The mules and donkeys that smugglers used traveled single file and could journey without guidance along familiar paths. Trained animals could also wait for their handlers at watering holes or home-in when separated from their masters. A major crossing region on the Rio Grande was located between the towns of Zapata and Los Ebanos, and the tequileros traveled through Zapata, Starr, and Jim Hogg counties to Duval County and a main distribution point—San Diego, Texas. From there, cars transported the liquor to major cities (San Antonio, Corpus Christi, Dallas, and Houston) throughout Texas.
More discreet businessmen than violent brigands, tequileros tried to avoid conflict and went so far as to ride through scrubland for days to evade detection. Despite their prudence, U. S. law enforcement viewed tequileros as the successors of the sediciosos of the previous decade and actively sought them out.
Confrontations between horseback smugglers and county, state, and federal law enforcement eventually ended tequilero operations. Mounted smugglers who did not lose their lives often lost their property, and this confiscation of equipment helped drive them out of business. The last five years of Prohibition saw only six reports of smugglers crossing through the brush in the counties adjacent to Laredo. Law enforcement’s final skirmish with tequileros occurred in Jim Hogg County in February 1927 when mounted customs inspectors killed one smuggler and seized several hundred bottles of alcohol and six horses. The ensuing years saw the occasional horseback liquor smuggler, but mounted caravans came to an end six years before the repeal of national Prohibition in 1933. Because they limited their activity to evading unpopular laws and resisted institutionally-racist Anglo authority in the process, ethnic Mexicans often valorized tequileros in spite of their illegal acts. Folk admiration of tequileros endures in period corridos (or romantic ballads) like “Los Tequileros,” “Dionisio Maldonado,” and “Laredo” still sung along the border.