You won't find a statue in Oregon honoring Ben Holladay, the man who promised to build the state's first real railroad and actually did it — but that's probably because of the way he did it.


He was a bold and driven speculator, ready to take a risk no matter what he had to do or whom he had to step on, as long as there was a glimmer of success.

"He was, in his day, a great, sturdy, successful man, who made great wealth and loved great power; a man who brooked no interference or opposition; who bought what he couldn't crush and dominated in all things possible; royal in his generosities, and vindictive in his disagreements," John Halloran, editor of the Daily Astorian, wrote shortly after Holladay's death in 1887.

Though most men's faults are forgiven and forgotten in their obituaries, Holladay's were all lined with the "sins" of his life — and yet, there was always a brief moment of admiration for what he had done.

"His death ends the career of one of the most remarkable men of any age or country," Halloran wrote.

"He was very hearty with his friends," wrote Lewis Baker, editor of the St. Paul, Minn., Daily Globe, who knew Holladay well, "but, very blunt with those not fortunate enough to have secured his good will."

In 1868, two railroad companies had been competing against each other for more than two years, trying to build a railroad south from Portland. They hadn't gotten far and both were heavily in debt.

Holladay, a 49-year-old multimillionaire, headed up the construction company for one of the railroads and was tired of what he called incompetent company leadership. He successfully demanded the directors immediately transfer all stock and bonds to him or he would stop construction. For his part, he agreed to assume all of their debt.

Finally, with his political influence — some say bribes — he was able to put the other railroad company out of business.

He had taken a virtually bankrupt company and, using his influence with business and banking contacts, was able to obtain enough credit and investment to begin building. Within three years, the Oregon and California Railroad had spent nearly $5.5 million in laying nearly 200 miles of track from the Willamette Valley to Roseburg, but that's where it stopped.

Freight and passenger revenue could no longer support construction costs. Loan interest payments were in default. And on Sept. 18, 1873, not only did Holladay's wife die, the stock market also crashed, setting off a long and deep economic depression. Holladay's life had reached its financial peak and now he had to fall.

In Weston, Mo., Ann Calvert was just 15 when Ben Holladay, who had only been in town a few months, decided he was going to marry her, something her father and mother utterly opposed. Even at age 20, Holladay was showing those characteristics that tended to antagonize just about everyone he met.

As Ann walked home from school one winter day in December 1839, Holladay caught up with her and, in his dominating style, told her he was irresistibly in love, was going to marry her, and she might as well get up on his horse. They rode to her great uncle's log cabin, called for a preacher, and that evening, Ann married Holladay, still wearing the apron she had worn to school.

Holladay said it was his first achievement in Weston, "the capture of my wife and the pacification of the old man."

Born in Kentucky, Holladay had learned how to handle a wagon from his father, who was a guide for immigrants passing through the Cumberland Gap, one of the main pioneer pathways through the Appalachian Mountains to the western frontier of Kentucky and Tennessee.

At 16, he came to Missouri and a year later was hired as private courier to Gen. Alexander Doniphan, a Missouri politician ordered to push Mormon settlers out of the state. Doniphan is credited with saving Mormon founder Joseph Smith's life by refusing execution orders, calling it "cold-blooded murder." A decade later, with the friendship of Brigham Young, Holladay, a Roman Catholic, established a profitable freighting contract from Kansas and Missouri to Salt Lake City.

Beginning with his humble saloon and hotel in Weston, where he sold "cheap Missouri whiskey," Holladay had begun amassing an empire.

"He had faults of disposition and education," Doniphan's son John, a Weston friend of Holladay's, told a book author years later, "but he was brave, strong, aggressive, talented, and generous. His life reads like a fable."

In 1862, already wealthy from government contracts and nonstop business ventures, Holladay acquired the failing Central Overland California and Pike's Peak Express Co., expanded the company's operations, and turned it into the Overland Stage Line. In November 1866, he sold out to Wells Fargo for $1.5 million, nearly $23 million today.

He owned hotels and mansions across the country, mines, two fleets of ships that dominated shipping between San Francisco and Portland, and the financial lives of others.

"He owned everything everywhere that turned a wheel — that made and unmade men," wrote Halloran as he described the "Napoleon of the West."

But this Napoleon's Waterloo was the Oregon and California Railroad.

By 1873, Holladay was squandering millions on a castle-like mansion and 1,000 acres along New York's Hudson River and taking out loans and issuing bonds to finance railroad construction. When anticipated revenues from freight and passengers failed, he attempted to pay the interest as it matured out of his private fortune, but then the stock market crashed, and it broke him.

In April 1876, investors took over Holladay's railroad and put Henry Villard in control.

"He (Holladay) was a man well-known to us," Halloran wrote. "Since '76 he has been but a shadow of his former self, and the last eleven years of his life were embittered by tedious litigation and financial embarrassment.

"The quiet voiced old man who loitered in gentle chat at the entrance to our hotel was in marked contrast to the Ben Holladay of former years."

Ben Holladay, 68, died July 8, 1887, in Portland.

Writer Bill Miller lives in Shady Cove. Reach him at