Ben Holladay is characterized as a devoted, diligent, enterprising man and a transportation magnate. He speculated in gold and silver mines, distilleries, general stores and slaughter houses, but he made his name and fortune in transportation.
While he is best known for starting the Concord Stagecoach to the
West, in the 1860s, Holladay established headquarters in an office at
the corner of California and Liedesdorff streets in San Francisco to
run his California, Oregon & Mexico Steamship Company.His vessels sailed between Francisco to the Southern states, and to Canada, Alaska, Mexico, Hawaii, and the Orient. Around 1861, Holladay took over steamers from Pacific Mail Line; this included the Cortez, Oregon, Sierra Nevada, Republic, Panama. His cabin fares between San Francisco and Portland were $45.00 and passengers unconcerned about food and accommodations could travel in steerage for $25.00.
At one point in his shipping career, it was said he owned all shipping in Oregon.
Competition was such that he established the North Pacific Transportation Company, which was comprised of his own shipping company and a Maine Yankee named Patton's Anchor Line and the California Steam Navigation Company. By 1869, this collaboration was operating ten side-wheelers and six propeller steamers north from San Francisco. The ships included Active, John L. Stephens, Moses Taylor, Oriflamme, Orizaba, Pacific, Panama, Senator, Sierra Nevada, Ajaz, California, Continental, Gussie Telfair, Idaho, Montana, Pelican.
Purportedly, Holladay's favorite ship, the Oriflamme, was built in 1864 as a fast naval gunboat and had engaged in China coastal trade. Holladay used this ship for private parties, some of which lasted all the way from San Francisco to Alaska.
In 1862, Holladay was the sole owner of the Overland Mail and Express Company and he is credited with introducing the Concord Stagecoach to the West. With Ben Holladay 's acquisition of the Butterfield Overland Dispatch in 1866, the name changed to Holladay Overland Mail and Express Company. He became known as the Stagecoach King. Combative and ruthless, he expanded and modernized; his Overland Mail & Express Company, running regular services across more than 3,000 miles (4,800km) of stage and freight lines from St. Louis to Salt Lake City and Oregon, was the biggest and most successful operation of its kind ever mounted.
He was the sole owner of some 20,000 vehicles, with more than 15,000 employees; passenger revenues often totalled $60,000 a month - the fare from Atchison, Kansas, to Salt Lake City was $350 - and over five years the US Post Office paid him nearly two million dollars.
Holladay moved from San Francisco to Oregon in 1868 in order to get involved in the railroad business. He stirred things up wherever he went and was decribed as "a bit of a dandy," dressing like a riverboat gambler. He was said to be "wholly destitute of fixed principles of honesty, morality, or common decency." Holladay's goal was to build a rail line to California along the east side of the Willamette River. In order to do so, he spent a total of $55,000 in bribe money to help secure his company's endorsement. He also built two large hotels in the area where the park bearing his name is now located.
The enterprising Holladay established Portland's first horse car line to connect the ferry at Front and F streets with downtown Portland. It was a muledrawn car, worn out from long usage in San Francisco before Holladay brought it to Portland, and it was pulled over iron rails from the turntable at Front and G streets down through town to Carruthers street, in South Portland, where another turntable was located.
On November 1, 1866, Ben Holladay sold his stagecoach company to Wells Fargo.
Ben Holladay lost his fortune in the stock market crash on September 18, 1873. In 1875, the bankrupt Holladay sold out to Goodall, Nelson & Perkins Steamship Company which reorganized the company as the Pacific Coast Steamship company.