Lillie Elizabeth Drennan and her husband Willard formally launched a trucking business in their native Texas. This enterprise, known as the Drennan Truck Line, would establish Lillie not only as a major force to be reckoned with in the Lone Star State’s freight industry but also as a transportation pioneer.
The Drennans started their trucking operations to take advantage of an oil boom near the city of Hempstead in eastern Texas. They routinely transported various supplies, including high-risk cargo such as TNT and dynamite, to workers in the oil fields. Willard Drennan, driving an open-cab Model T Ford truck, initially handled these deliveries. In no time at all, however, the business was thriving and Lillie – driving a closed-cab Chevrolet truck – began delivering supplies as well. The couple soon acquired more trucks for their fleet and hired additional drivers.
Lillie Elizabeth Drennan had been born in Galveston in 1897. She dropped out of school when she was only in the fifth grade and entered the workforce as a telephone operator at the age of 13. When she was 15, she married William Barney Jackson; their marriage lasted a year-and-a-half. Lillie married Willard Drennan in 1917. Just over a year after they had launched the Drennan Truck Line, however, they were divorced. Lillie then became sole owner of the business.
It was around this time that, in compliance with the newly enacted requirements of the Texas Railroad Commission for overall motor-freight operations in the state, Lillie applied for a commercial truck- driver’s license. At first, the commission’s examiners hesitated to grant her a license. While the official reason for this reluctance was her hearing impairment (likely the result of a bout with scarlet fever several years earlier), Lillie perceived that the underlying motive might actually involve gender bias.
Lillie, therefore, made a forceful case for being granted a license, highlighting her exemplary driving record at a commission hearing. She told the examiners, “If any man can beat my record I’ll just get out of here.” Lillie prevailed and, in doing so, made transportation history as the first woman to receive a commercial truck-driver’s license in Texas. She was also one of the first women, if not the first woman, to obtain this type of license in the entire United States.
Over the next 23 years, Lillie continued to run the Drennan Truck Line with considerable success. (Incidentally, she married again in 1931; this marriage to S.B. Boulware ended in divorce in 1943.) Lillie supervised her fleet of drivers with an iron fist. She also still took time to drive those trucks as well, something she highlighted at a meeting of the San Antonio Traffic Club in the fall of 1943.
“I know what it is to wade in mud above my boot tops to get my trucks through to their destination; I know what it is to sit behind the steering wheel of any truck for 48 hours without rest or sleep; I know what it is to have my truck break down on a lonely stretch on one of these cold Texas nights,” she told the group. Lillie also emphasized, “I am no desk trucker.”
With her lively personality and trademark 10-gallon Stetson hat, Lillie attracted attention well beyond the borders of Texas. The Los Angeles Times called her a “dry land Tugboat Annie.” One trucking trade publication characterized her as “a twentieth-century pioneer who has all the color of an Annie Oakley, and who lives the life of a hard-hitting frontiers-woman.”
Lillie also achieved a great deal of acclaim for her driving record, earning safety awards from the Texas Railroad Commission and the Texas Motor Transportation Association. In 1946, one veteran insurance carrier in Texas wrote that he knew of “no other truck owner” in the state who rivaled Lillie’s safety record. Lillie remained in business until 1952, when she sold the Drennan Truck Line to a larger firm. She died in 1974.
For more information on Lillie Elizabeth Drennan, please check out https://tshaonline.org/handbook/online/articles/fdr15.
Transportation History 
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