James Saunders Penn, founder of the Laredo Times, the eleventh child of C. C. and Frances (Reeves) Penn, was born at Clinton, Mississippi, on July 13, 1846. The family had moved there from Virginia. In 1855 they moved to Rutersville, Fayette County, Texas, where the elder Penns, who were devout Methodists, became involved in community affairs. For a short time Penn attended a college near Gonzales. During the Civil War in 1862 he enlisted in the Fifth Regiment of Sibley's Brigade and saw combat in Louisiana and Arkansas. After the war he settled briefly at San Felipe before fleeing to Brazil, where he worked in the mercantile business in Rio de Janeiro for five years. He returned to Texas, where he married Virginia Josephine Muller (or Miller) on February 29, 1872. The Penns had three daughters and two sons.
Penn had a printing business, J. S. Penn and Brother, located in both San Antonio and Austin. In May 1881 he moved his printing equipment to Laredo and began publication of the Laredo Times on June 14. His first sensational story was of the assassination of President James A. Garfield on July 6. On September 6, 1883, Penn began publication of a daily edition that was delivered by 4 P.M., although he still continued to publish a weekly edition. In 1884 he used his editorials in the Laredo Times to criticize the Botas, a local faction of the Democratic party that controlled Laredo and Webb County (see BOTAS AND GUARACHES). He accused Raymond Martin, leader of the Botas, of wide-scale corruption and cited contracts between the city of Laredo and the Laredo Waterworks and Laredo Street Railway Company, both owned by Martin. Between September and November 1884 Penn also ran articles on the excessive cost of building the new Webb County Courthouse and jail. He also editorialized against the dirty and unpaved streets of the town. At the same time Penn praised the Guaraches, another faction of the Democratic party, who were parading under the banner of reform. Following the bloody election riot of April 7, 1886, Penn switched allegiance to the Botas after being nominated for state representative. He lost the election when four of the seven precincts in Starr County were thrown out due to a "clerical error."
In 1887 Penn was confined to a mental institution in Austin, after which his son, James Saunders Penn, Jr., continued publication of the paper. Penn returned to his duties as editor and publisher but suffered a relapse in 1901 and was returned to the asylum. He was released and returned to Laredo but committed suicide on May 17, 1901, after he had shot and killed a friend, W. R. Pace. Penn is buried beside his wife in the Laredo City Cemetery.