Benjamin Holladay learned the freight business at an early age and left home in his late teens for a road trip to Santa Fe in what was then Mexico.

He then settled in Weston, Missouri, where he worked as a store clerk before serving as courier during the 1838 Mormon War for the state militia.

[2] After working at the store for a few years he opened a tavern and hotel in 1840, as well as starting what would become the McCormick Distilling Company, which claims to be the oldest distillery still operating in the same location.

Holladay acquired the Pony Express in 1862 after it failed to garner a postal contract for its owners, Russell, Majors and Waddell.

Traveling to New York from San Francisco in July, 1862 Holladay was almost killed when the SS Golden Gate sank off Manzanillo.

[3][4] Between the Overland Trail and six other routes, Holladay received government subsidies totaling nearly $6 million over a four-year period.

[6] Holladay's "Eastsiders" completed 20 miles (32 km) of track before the competition, using "every trick known to man" in the construction, including bribing the Oregon Legislature in October 1868.

"[6] After buying a large home from Doctor Rodney Glisan, "he remodelled it and immediately installed a harem of high class prostitutes.

They were the parents of:[11] Holladay died in Portland, Oregon, on July 8, 1887,[7] and is buried at Mount Calvary Cemetery in that city.

[2] An ordinance came into effect on June 1, 1866 renaming McGaa Street in Denver, Colorado to Holladay to honor the tycoon.