The Laredo Times was founded by James Saunders Penn as a weekly newspaper on June 14, 1881. Penn had moved his printing equipment from Austin to Laredo in three prairie schooners shortly before the railroads reached the town. It was a four-page weekly, three columns on the front page being devoted to news items and editorials. A second page also carried editorials, news items, and legal notices, while the back pages consisted of advertisements and local items. All the type was set by hand. The first sensational story carried by the Times was the assassination of President James A. Garfield on July 6, 1881. In September 1883 the weekly edition had grown to twelve pages, and Penn began publishing the Laredo Daily Times. Through his editorials Penn became a leading voice for municipal reform. In the news section he launched investigations of the county jails, city construction projects, and the city's ferry franchise. After his father's death in 1901, James Saunders Penn, Jr. (Justo), followed his father in the management of the paper. He improved the equipment, changed the format, and devoted the front page to local, state, and national news. The paper grew into one of the most influential publications in South Texas.
In 1926 Penn sold the Laredo Times to a corporation headed by H. J. Hanway, with William Prescott Allen and Oliver W. Killam as major shareholders. Shortly thereafter the weekly edition was discontinued. A new feature of the Times was the daily Spanish section, "El Tiempo de Laredo," which consisted of two pages on weekdays and four on Sunday. In that day the Times was the only English-language paper on the border to carry a Spanish section. In 1928 it became part of Newspapers, Incorporated, of which Allen was a major stockholder. As the publisher, Allen was awarded the Águila Aztec Medal by Mexican president Manuel Ávila Camacho for his work in Mexican-American relations. Herschiel L. Hunt became the editor in August 1934. In 1970 the Times was sold to the Jefferson Pilot Corporation. James H. Hale was the publisher and editor at this time. In 1979 William H. Baker became the publisher, and in March 1981 Mike Herrera III was the first native Laredoan to become publisher. Herrera at this time was the only Mexican-American publisher of a major daily paper in Texas. In December 1984 the paper was bought by the Hearst Corporation. In 1986 William Green became the publisher. The Spanish section continued to be a part of the daily and Sunday paper.
The first Laredo Times office was located at the southeast corner of Flores and Farragut. The newspaper later expanded to larger quarters on the south side of Jarvis Plaza and in the 1930s moved to Matamoros Street in downtown Laredo. It moved again in 1972 to a location just off Interstate 35 on Esperanza Drive.