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Many of the first trucks were nothing more than converted automobiles, which weighed more than the loads they could carry and could not travel long distances without breaking down. For these reasons, trucks were confined to city driving. In the early 1900s, the nation depended on railroads for the distribution of freight across the country. The poor condition of roads and the absence of a national highway system, as well as the mechanical limitations of trucks, made the shipment of goods by truck impractical. In 1904, there were only about 500 trucks in the United States.

Despite these initial obstacles, the first long-distance trip made by a truck carrying freight occurred in 1911. The truck was called the Pioneer Freighter, weighed 7 tons loaded, and traveled from Denver to Los Angeles in 66 days. Five years after the Pioneer Freighter's debut, the number of trucks in the United States had grown to about 1 million. Still, trucks were mainly used to deliver goods within short distances, because trucks were faster and had more flexible schedules than trains.

During the Great Depression, the trucking industry also experienced increasing competition among carriers. With many people out of work, anyone with a car could convert it into a truck and offer their services to merchants. This practice led to dangerous and unsafe shipping, because these trucks were often overloaded and mechanically unsound. In 1933, the American Trucking Association helped legitimate carriers bring regulation to the trucking industry. Upon the ATA's recommendations, the government passed the Motor Carrier Act (MCA) of 1935 to prevent destructive competition. For 40 years, the Motor Carrier Act ensured that large cities and small towns, as well as large and small industries, received equal service from carriers. A small company could exist without the threat of being driven out of business by a larger carrier that could afford to cut its rates, since the MCA required equal rates for equal services.

In addition to benefiting from protective regulations, the trucking industry began to flourish with the development of new and more specialized trucks. Tank trucks were built to carry fuel, and trucks were designed for transporting livestock, produce, milk, eggs, meat, and heavy machine parts. The development of the detachable trailer further increased truck efficiency. Depending on what needed to be shipped, a different trailer could be hooked up to the tractor, allowing carriers to provide specialized services to a greater variety of customers.

Increased manufacturing output during World War II and the economic prosperity that followed the war continued to boost the trucking industry. The efficiency of shipping freight by truck improved further when the Federal Highway Act of 1956 mandated the building of 42,500 miles of interstate highways. By 1970, revenue from trucking was $14.4 billion, while the revenue from railroads was only $11.1 billion.

In the 1970s, many critics argued that while the MCA of 1935 had been necessary to protect this growing industry, it was now a detriment because it did not allow for competitive rates. The result of this argument was the Motor Carrier Act of 1980, otherwise known as deregulation. The MCA of 1980 allowed companies to expand the number of routes they could serve. The act also allowed many nonunion companies to spring up. In many cases, these nonunion companies were able to charge clients half of what union companies charged for shipping. Between 1980 and 1986, more than 32,000 new carriers received operating licenses from the Interstate Commerce Commission.

Many companies were hurt by deregulation; however, the competitive climate in the trucking industry, while still strong, is less chaotic than it was in the 1980s; carriers and shippers often found that too much rate cutting led to a serious decline in the quality of service available. Today, employers must face the challenge of attracting and keeping qualified drivers, as well as the threat of terrorism, a recent development for the trucking industry. The prospect of terrorist attacks has had a significant impact on safety and security measures and how trucking companies conduct their business.