Los Tequileros: Adventures in Prohibition-era smuggling

Tequileros (literally translated as tequila people) were smugglers of the U.S. Prohibition era (1920-33) who transported liquor illegally from Mexico into the United States for profit. They typically operated through rural South Texas, navigating back trails and making use of low-water crossings along the Rio Grande that divides the two countries.

These smugglers were usually male, ethnic Mexican (or Tejano), and often used donkeys and horses to transport their alcohol. 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.

Tequileros used horses, mules, and donkeys in their operations. Horses carried the smugglers, while mules and donkeys served to convey their contraband cargoes.

Tequileros proved adept at packing their draft animals. A skilled packer could fit 50 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.

Tequileros trained their animals well and used them expertly. Mules and donkeys traveled single file and could journey without tequileros’ guidance along familiar paths. Trained animals could also wait for their handlers at watering holes or home-in when separated from their masters.

Texas Ranger Jesse Perez recounted that officers in the lower Rio Grande Valley were continually frustrated by an animal they dubbed the “Lone Rum-Running Jackass of Starr County,” whose special talent consisted of its ability to find its way home alone at night. During the day, the burro’s handler guided the gifted animal across the river into Mexico where it would be loaded with liquor at nightfall. After loading, smugglers released the animal, confident it would make its way back home where its master waited. Officers’ morning discoveries of a lone pair of tracks emerging from the river provided silent testimony of the burro’s success.

More discreet businessmen than violent brigands, tequileros tried to avoid conflict, going so far as to ride through scrubland for days to evade detection. Despite their prudence, U.S. law enforcement viewed tequileros as armed invaders and the successors of the sedicisos 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 south of Corpus Christi, (primarily Zapata County, Duval County in the San Diego area and Jim Hogg County in the Hebbronville-Randado zone).

Law enforcement’s final skirmish with tequileros occurred in Jim Hogg County in February of 1927 when mounted Customs inspectors killed one smuggler and seized 700 bottles of alcohol and six horses. Future years would see 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 (Tejanos) 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” that are still sung along the border and in the South Texas Brush Country.

Decades after his death at the hands of U.S. law enforcement, family members disinterred tequilero Leandro Villarreal from the unhallowed grave where Texas Rangers had left him. Rather than rebury him quietly, family members took pride in the legend that Leandro became in his last moments. On Nov. 10, 2000, family members and locals celebrated Leandro’s life in a memorial mass held at Our Lady of Lourdes Catholic Church in Zapata.

Not only did information regarding Leandro’s role in the song “Los Tequileros” appear in newspaper coverage of the event, family members chose to forever embrace Leandro’s past as a liquor smuggler by literally chiseling it in the stone above his grave. The fact that the artisan who completed the headstone took no pay for his labor, but provided the monument at cost makes clear Leandro’s reverence beyond his family and typifies tequileros’ place of honor within the Tejano community.

George T. Díaz is an assistant professor of history at the University of Texas-Rio Grande Valley. His dissertation was on “Contrabandista Communities: States and Smugglers in the Lower Rio Grande Borderlands, 1848-1945” and his master’s thesis was titled: “When the River Ran Red: Prohibition on the Central South Texas Border, 1919 –1933.” Excerpts for this article came from his book “Border Contraband: A History of Smuggling Across the Rio Grande."