Benjamin Holladay was born on October 19, 1819 in Nicholas County, Kentucky, United States. He was the son of William and Margaret (Hughes) Holladay. In early boyhood he removed with his parents to western Missouri, where the years of his young manhood were passed.
Holladay had little schooling.
Holladay operated a store and a hotel in Weston, and engaged in trade with the Indians in Kansas. At the outbreak of the Mexican War he furnished supplies for Kearny's Army of the West. When the war ended he purchased at bargain prices oxen and wagons from the government. With T. F. Warner as partner he launched a trade venture to Salt Lake City with fifty wagon-loads of merchandise. A letter of recommendation from Colonel A. W. Doniphan, who had befriended the Mormons during their troubles in Missouri, gave Holladay a favorable introduction to Brigham Young which insured success for his business undertaking in Utah. The following year he bought cattle, drove them to California, and sold them at a handsome profit.
Successful business ventures throughout the fifties increased his resources. He advanced money to Russell, Majors, and Waddell; and when this great overland freighting firm went to the wall, he bought their Central Overland California and Pike's Peak Express Company for $100, 000. He set to work reorganizing, extending, and improving the overland stagecoach service until under him it reached its greatest extent. For a time the mail contract paid more than one million dollars annually and the passenger traffic from the Missouri River to the Golden Gate was correspondingly large, but during the Indian uprising on the Plains in 1864-1865, when stage stations, equipment, and supplies were destroyed, Holladay suffered heavy losses.
He subsequently placed claims against the government for these losses, but they were never paid. With the coming of the railroad he read the doom of the stagecoach and sold out his staging business to Wells, Fargo and Company (1866). He had already organized in 1863 the California, Oregon, and Mexican Steamship Company, and four years later he formed the Northern Pacific Transportation Company, which operated vessels in an area extending from Sitka to Mexico.
In 1868 he plunged into a railroad fight in Oregon and became the chief owner of the Oregon Central Railroad Company. He sold some of his railroad bonds in Germany. Railroad construction was pushed with vigor and money was spent extravagantly until some 240 miles of railroad had been built in Oregon. When financial difficulties arose he sold steamship interests to bolster his railroad projects. The panic of 1873 staggered him. Finally the German bondholders took over the railroad and eliminated Holladay. With his retirement from the Oregon railroad system in 1876 his financial power was broken and was never regained.
He died in Portland in his sixty-eighth year.
Holladay is best remembered as a transportation magnate. He speculated in gold and silver mines, distilleries, general stores and slaughter houses, but he was said to have made a great deal of money selling supplies to the U. S. Government during the Mexican War, but is best known for making his name and fortune in transportation.
Henry Villard described Holladay as "illiterate, coarse, boastful, false, and cunning. " Holladay's attorney, John Doniphan, described him as possessing "many of the characteristics of Napoleon. "
He was known for having "the bearing of one born to command", and for "being clever, shrewd, cunning, illiterate, coarse, and completely unscrupulous". Joseph Gaston described him as being "wholly destitute of fixed principles of honesty, morality, or common decency. "
At Weston, Missouri, Holladay met and became engaged to Notley Ann Calvert. The girl's parents objected to the match, so the young couple eloped and were married at the log-cabin home of the bride's uncle, Captain Andrew Johnson.
In the days of his success Holladay maintained a beautiful residence in Washington, and built a mansion, "Ophir Place, " on the Hudson River near White Plains. His two daughters by his first wife married titled Europeans. Left a widower in 1873, the following year he married Lydia Esther Campbell, by whom he had two children. None of the seven children of the first marriage survived him.
