‘The UPS Man’: All in the Delivery

The Wall Street Journal , October 24, 2026

When a 19-year-old James E. Casey started his third delivery business in 1907, there was no reason to expect it to last longer than his first two. Delivery was an easy business to enter, and competition was fierce.

What began as American Messenger endured. Casey led it for much of the 20th century, resigning from the board of the company he created shortly before his death at age 95. As the title of Marc Levinson’s “The UPS Man” reveals, today we know the company as United Parcel Service. Its brown trucks seem to have always been around. Yet for much of its history, UPS worked exclusively in a few large cities. Its story is one of pivots and evolution. As the company grew, it navigated and exploited the 20th century’s tangle of transport regulation.

Mr. Levinson’s books include “The Box” (2006), on the shipping container, and “The Great A&P” (2011), on the struggle between the low-price chain and small grocers. “The UPS Man” similarly explores radical innovations in the distribution ecosystem. Even without access to personal writings or company archives, Mr. Levinson uses legal documents and other records to reconstruct an unlikely saga in which the ever-optimistic Casey turns even seemingly disastrous events, such as the Great Depression, to the benefit of UPS.

Casey and a partner started American Messenger by borrowing $100 (around $3,600 today) from a family friend and setting up in the basement of a Seattle saloon. They relied on a bicycle and the city’s streetcars for transportation. Although they handled messages and other errands, the partners hoped to provide a service that would remain UPS’s core business until the 1960s: delivering shoppers’ purchases for retailers. But shops were reluctant to rely on a company that might quickly go out of business.

In 1909 Casey came up with a crucial innovation. A local menswear store replaced its part-time carriers with American Messenger when Casey offered a monthly rate capped at 17.5 cents a parcel. In exchange for the low rate, Casey demanded exclusivity. The store would bring each day’s packages to American Messenger’s office, where they would be combined for delivery with those of one-off customers paying higher rates.

“Consolidation seems a simple step, but it distinguished the company from its competitors,” Mr. Levinson writes. “It transformed American Messenger from a traditional messenger service into a different type of business, a delivery service.” This marked the first step toward the hub-and-spoke strategy that would define UPS.

In 1915, two years after merging with another messenger company and taking on a third partner, the newly named Merchants Parcel Delivery won a two-year contract with a hardware store that closed its in-house delivery department. The contract assured other retailers that they could trust Merchants Parcel to stick around, leading to more long-term commitments. A year later the business enlisted a fourth partner, who invested $10,000 and brought industry experience and organizational talent. The quartet agreed to concentrate entirely on retail deliveries.

These formative events all occurred when delivery was a wide-open business. Permissionless innovation ruled. But the window of entrepreneurial opportunity was closing, even as Casey and his partners sought to expand to California. Starting in 1917, the state became one of the first to require trucking companies to get regulatory permission to enter the delivery market. Any new entrant had to prove that “public convenience and necessity” required its services. Contract carriers, with deals like the ones Merchants Parcel had with stores, would need permission to operate. Common carriers offering trucking to all comers also had to get approval for their rates and routes. Eventually other states and the federal government adopted similar regulations. For most of the 20th century, hiring good lawyers was as important to profitably moving goods as implementing efficient sorting operations.

Merchants Parcel expanded to California in 1919 when Casey and his partners acquired an Oakland company that enjoyed operating privileges from the preregulation days. Entry into the Bay Area brought a final name change, to United Parcel Service, avoiding confusion with another local company. The partners expanded to Los Angeles in 1922 by buying two more trucking businesses—both common carriers—for shares in the company. UPS would remain owned almost entirely by its managers until its initial public offering in 1999.

With these acquisitions came the company’s first experience with regulatory carve-outs, which would prove essential to its success. Common carriers were supposed to haul everything at set rates. Regulators allowed UPS to charge higher rates for items too large for a single person to lift. Common carriers were also required to stick to prespecified routes. Regulators allowed UPS to deviate to reach suburban homes. Parcel delivery, California regulators declared in 1926, was “essentially different” from other trucking and deserved special consideration, language others would follow. “In case after case,” Mr. Levinson writes, “UPS would win permission to do things that other trucking companies could not.”

From its early days, however, the company was happy to use regulation to squelch competitors. In 1927 UPS complained to regulators about an unlicensed Los Angeles startup offering sorting and delivery at rates matching those of UPS. Regulators cracked down, ruining the business, which UPS then bought.

By World War II, the company’s combination of operational and regulatory know-how allowed it to expand, giving UPS a de facto monopoly on the delivery of retailers’ parcels on the West Coast as well as in the Northeast and the larger cities of the Midwest. “The threats to its bottom line were not that some other company would seduce its customers but that consumers would change their habits,” Mr. Levinson writes. That is what happened as stores and their customers decamped to the car-oriented suburbs and demand for retail deliveries shrank.

In response, Casey in 1954 outlined a bold vision for a transformed company. UPS would deliver small packages for wholesalers “by automobile or airplane, to any city or town in the United States, within two days, at rates lower than by any other means of transportation.” That strategy would transform UPS from a retail-delivery service with sorting concentrated in urban downtowns into a business-to-business carrier, with clients and nighttime sorting hubs all over the country.

This change required reorganization, large capital investments, and aggressive public-relations and lobbying campaigns to win the necessary regulatory and legal permissions. When Casey retired as chairman and chief executive in 1962, UPS was transporting 107 million packages a year between cities and expanding fast.

By the time Casey died in 1983, the freight world had returned to the fierce competition of the early days. Trucking, railroads and airlines had all been deregulated, essentially declaring the 20th century’s experiment in regulation a wasteful mistake. UPS was organizationally sound and unusually good at the tricky last mile of delivery operations. But without regulatory protection from competition, profits were harder to come by. Since then, customers have enjoyed more of the benefits.