Benjamin Franklin Dillingham

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Benjamin Franklin Dillingham
Benjamin Franklin Dillingham.jpg
Born (1844-08-04)August 4, 1844
Cape Cod, Massachusetts
Died April 7, 1918(1918-04-07) (aged 73)
Oahu, Hawaii
Occupation Businessman
Spouse(s) Emma Louise Smith
Children Walter F. Dillingham
Parent(s) Benjamin C. Dillingham
Lydia Sears Howe

Benjamin Franklin Dillingham (August 4, 1844 – April 7, 1918) was a businessman and industrialist during the late Kingdom of Hawaii era, throughout the period of the Republic of Hawaii, and during the first two decades of the Territory of Hawaii. Dillingham was a New Englander, born on Cape Cod in 1844, and he went to sea at the age of 14. After a series of adventures, and rapid advancement, he landed in Honolulu as first mate aboard the bark Whistler in 1864. He was 20. After breaking his leg in the topple from the horse, he was carried to the American Marine Hospital in Nu'uanu to heal. The Whistler sailed without him, and Dillingham was an ex-seafaring man, ashore for good.

After recuperating, he found work at a local hardware store. An entrepreneurial spirit bubbled within, and in a few years he had borrowed some money and was its owner. He also married a missionary daughter and started a family. Frank Dillingham's business—the hardware operation and later a large dairy—struggled with heavy obligations for decades, and he was constantly searching for a 'big score' that would eradicate his debts and provide for his family.

That score was Oahu Railway & Land Company, a narrow-gauge operation that established sugar as a phenomenally profitable crop on O'ahu. The primary line headed west from the main station in downtown Honolulu, eventually stitching together sugarcane plantations in 'Aiea, Waipahu, 'Ewa, Wai'anae, Waialua, and Kahuku.A later branch winding its way to the centre of the Island served the pineapple growers around Wahiawa. For almost 60 years—from 1889 to 1947—OR&L trundled both freight and passengers around the island creating great fortunes not only for the Dillinghams, but for many others as well.[1]


Benjamin Franklin Dillingham (1844–1918).jpg

Dillingham was born on September 4, 1844 into an old New England family in Cape Cod, Massachusetts. His father was Benjamin C. Dillingham and mother was Lydia Sears Howe. At the age of fourteen he became a sailor on the Yankee clipper Southern Cross which was captured and destroyed by the Confederate steamer Florida in 1863 during the American Civil War. In 1865 he became first mate of a barque named Whistler that did a regular run between San Francisco and Honolulu. On his third trip to the island kingdom, Dillingham broke his leg after falling from a horse and was forced to convalesce in Hawaii.

...from sailor to trainman[edit]

Benjamin Franklin Dillingham went to sea at the age of 14, not an unusual choice—or age—for a farm boy from New England. Perhaps it was in his blood, as his father had made the same decision as a young man.

Dillingham was bright, disciplined and hard working, three traits worthy of rapid advancement, then or now. While still a teenager, he circled the globe and even became an unwitting prisoner of war.

On June 6, 1863, he was nineteen-year-old third mate on the clipper ship Southern Cross bound for New York with a cargo of "log wood" when the heavily armed Confederate raider CSS Florida appeared. British-built, the Florida was iron-hulled and powered by both sail and steam.

Clipper ship Southern Cross leaving Boston Harbor, 1851, by Fitz Hugh Lane

As a disguise, her smokestacks were even collapsible. The Southern Cross was becalmed, her sails flapping, so there was no hope of escape. On this day Florida was flying the British ensign, though as she steamed closer, she ran up the rebels' "stars and bars." A squad of armed Confederate sailors boarded and took Dillingham and the rest of the clipper's small crew prisoner. Then, as the new prisoners watched from the deck of their captor, the Southern Cross was set ablaze and sunk.

According to a memoir that Frank Dilligham penned years later, discipline was lax aboard the captor ship: At the time of our transfer to the Florida, Captain Moffit was so much under the influence of liquor that he was unable to walk the deck without losing his equilibrium. The usual disciple of naval ships was sadly wanting.

One night Dillingham loosed his handcuffs and briefly considered taking control of the Florida but reason prevailed when he realized that his thirteen men—the other twelve still in shackles—would be facing the 325 men of the Florida. Eventually they were put ashore at Rio de Janeiro and worked their way back to the war-torn United States.

Dillingham headed west, determined to take up residence in San Francisco and find work ashore. An unsuccessful hunt for employment led him back to the sea, and in 1865 he was hired by Captain John Paty as first mate on the bark whistler, on the San Francisco/Honolulu run. "A brief sojourn in the city enabled me to realize that I had no training in any other vocation, save that of the sea, and learning that Capt. Paty of the bark Whistler plying between the coast and Honolulu was in need of officers, I applied and obtained the position of first mate without delay."

Paty was already well renowned in the Pacific. Kamehameha III made him a Commodore in 1846, and Paty had later claimed Laysan and Lisianski Island, both Northwest of the main archipelago for the kingdom. Dillingham wrote that he felt at home the first time he came ashore in Honolulu. After my tempestuous experiences in rounding Cape Horn and the Cape of Good Hope, the trip seemed to me like a pleasure excursion. It felt as if I had anchored in a home port; the cordiality I experienced from all those whom I met removed at once the feeling of being in a foreign land though the streets were filled with several nationalities. The luxuriant foliage, the balmy breezes, the tropical fruits, all afforded such delights that I felt sure I should return.

He would indeed return, and on his third trip aboard the Whistler, he rented a horse. "Sailors are notoriously unfamiliar with horses" he later wrote—describing his collision with a carriage. Ships and sailors were of economic import in the Islands, and on July 29, 1865, the Pacific Commercial Advertiser ran a short piece on his accident: The first officer of the bark Whistler Mr Dillingham, whose leg was broken last Friday night by being thrown from a horse, in a collision with a carriage on the vally road, is now at the American Marine Hospital, where he receives every care and attention, and is in a favorable condition for recovery

The Whistler could not wait and sailed without him. While recovering, Dillingham had a long time to reflect upon his options. This time he was more serious about staying ashore. Already in love with these Islands, he had met Emma Louise Smith on an earlier visit. Despite apocryphal tales of her nursing him back to health, she was away in New England while Frank was recuperating. She was also engaged to another man whom by all accounts she did not love. Dillingham's patience in slowly courting Emma demonstrated a determination for which he later became known.

He accepted a job as a clerk in a hardware store called H. Diamond & Son for $40 per month. The store was owned by Henry Diamond, formally a bookbinder in the Seventh Missionary Company. In 1850 he had been released from his duties at the Mission and had gone into business with his son.

Meanwhile, Dillingham turned down a tempting offer to captain the Whistler on a voyage 'round the Horn to New Bedford, Massachusetts. It would have been very rewarding financially and given him a chance to see his family, but it would have taken upwards of a year. He turned it down. Frank Dillingham was ashore for good.

He worked for "Father" Diamond and by 1869 was offered to buy out the concern for $28,000, the cost of the inventory. As a born entrepreneur, Frank agreed, but of course did not have the money. What he did have, which was almost as goo, was a contact with Alfred Castle, then working for the Kingdom. Castle's father was Samuel Northrup Castle, who had arrived in 1837 with the Eighth Company to work in the Mission's business office. He and Amos Starr Cooke had later formed the mercantile firm of Castle & Cooke. Mr. Castle, of course, did have access to $28,000, an enormous sum of money in those days.

The two young men became partners in the venture, and—with S.N. Castle's guarantee—they borrowed half the money from Charles R. Bishop's bank and gave Diamond notes for the other half. The new company was to be called Dillingham & Co. It was an enormous risk, especially in Hawaii's fragile economy. But just a decade before Dillingham had been a 14-year-old scampering up the rigging of the tall ship Southern Cross. He was well used to the risks.

In his personal life, Frank had finally connected with Emma Smith. Her parents, Reverend Lowell and Abigail Smith, were members of the Sixth Company of missionaries and had arrived in the Islands some three decades earlier, in 1833. Emma was born in 1844, so she and Frank were the same age. She broke her engagement and began seeing Dillingham. they were married on April 26, 1869 in Kaumakapili Church with her father officiating.

Frank now had a new partner in business and a new partner in life. He and Emma had both made an excellent choice in mates, and her support of Frank for almost a half a century was legendary.

He was not so lucky in business. This was a dubious period in Hawaii's commercial climate—staggering though the transition between whaling's collapse and the rise of sugar. Large suppliers pulled Dillingham's credit lines, and his accounts here were paid late. Yet he had to offer credit, even while being denied it, and an 1872 ad offers buyers "the most Liberal Terms." To exacerbate matters, Alfred Castle died suddenly in 1874, barely 30 years old, leaving a widow and two young daughters.

Castle and Dillingham had a verbal agreement that Frank would buy out the partnership, but Castle had died before they committed it to paper. Now there were a widow and small children, and a bereaved S.N. Castle negotiating with Frank on their behalf. the process was a long one for all concerned, but was eventually settled. Dillingham was on to bigger things.

James Campbell, one of the wealthiest landowners in Hawaii
James Campbell, one of the wealthiest landowners in Hawaii

The conundrum facing Dillingham was that he had been offered the opportunity to buy James Campbell's 56,000 acres in 'Ewa and Kahuku but could not raise the money in Hawaii. Investors here still thought Campbell was crazy for paying $154,500 for the two parcels a few years earlier. Investing with Dillingham at $600,000 for the same property seemed even more insane. both tracts were considered too far away, and even though Campbell had bought it in artesian water there in 1879, 'Ewa was envisioned as a dry wasteland.

Dillingham could not raise the money offshore either, as investors there were worried about Hawaii's political climate. Campbell's living heirs should be ecstatic that the long-ago land sale to Dillingham fell apart, as the estate is still disbursing substantial monies generated from that land to a number of them.

Dillingham could solve the transportation problem with a railroad, of course, but since there was nothing out there to speak of—an infintesimal number of people and almost no freight—he could not justify the huge cost of a train. The key to it all was water. So long as there was almost none and the 'Ewa plain would barely support grazing cattle, then purchasing of the land or running a railroad would not capture willing investors.

In 1879 Campbell had bought in James Ashley, a California well driller who struck artesian water at Honouliuli in the 'Ewa district, a sign that the arid lands there could quickly become lush. Dillingham was a believer, but since he could not raise the capital to buy the two tracts outright, Campbell offered to lease the land to him for half a century for $50,000 a year.

Dillingham accepted and understood that to make the deal profitable he had to provide cheap, reliable transportation. He had now established the "& Land" portion of his corporate name, so all he needed was the cap[ital and technical skills to create the "Oahu Railway" part. And, of course, he needed a railroad franchise from the monarchy.

Once he secured some tentative start-up financing, Dillingham approached the government for legislative approval. A decade earlier, in 1878, King Kalakaua had signed "An Act to Promote the Construction of Rail-ways," and within a year, the first passengers road between Kahului and Wailuku on Maui. Soon after that, in 1880, the Hawaiian Railroad Company had been chartered to run out of Mahukona on the Big Island. So 'Oahu, late to the sugar business, was late to the railroad one as well.

On September 4, 1888—Frank Dillingham's 44th birthday—the legislature voted to give him the franchise for his proposed new railroad. And a week later king Kalakaua signed it into law. Given the enormous capital outlay on Dillingham's part, it was not a particularly generous document, running for just twenty years with no government subsidies. The charter also demanded quick action—an operational steam railway from Honolulu to the Pearl River Lagoon (it was not yet Pearl Harbor) within just three years.

Quick action was something the entrepreneurial Dillingham was well equipped to provide. The right-of-way had to acquired, then cleared and prepared for the track gangs. People had to be hired, material ordered, important decisions made. Paradise of the Pacific magazine summed up these events in July 1892, almost four years later.

"Now that you have secured your franchise, when will the road be commenced?" was asked of Mr. Dillingham on the same day by one of those who looked upon the scheme as feasible.

"This is my birthday," said Mr. Dillingham, "and one year from today you may have a ride on the Oahu Railroad." The difficulties in the way of keeping this promise may be imagined when it is stated that not a blow had yet been struck nor a dollar subscribed, and that the enterprise did not find favor with the monied men. To incorporate a company with a capital of $700,000 was the next step, and, under the circumstances, was no easy matter.

No easy matter or not, the indefatigable Dillingham forged ahead. Barely six months later, on March 9, 1889, a ceremonial groundbreaking occurred at Samuel M. Damon's estate at Moanalua, with Frank Dillingham's young son Harold turning over the first spade of earth. According to the Advertiser:

The shovel which was used on the occasion by the Dillingham boy is still preserved. Money could not buy this token or souvenir from the man who made the railroad and who, at the same time, created prosperity for the country by making possible several of the grandest industrial estates in the world.

From that moment, there was no stopping the enterprise.

The legislature awarded the charter to Dillingham personally. He transferred it to the corporation of which he was not even an officer. Instead he took the position of General Manager, and, during the construction phase of the Pearl River Division, he was hired as a contractor—we would call him General Contractor today—for the road. He took ultimate responsibility for completing his own dream. And he consistently built for the future, using far better materials and workmanship than he had to. The Pacific Commercial Advertiser reported on an organizational meeting on April 12, 1889, at which "The Promise" was again noted: At the meeting of the Oahu Railway and land company, held yesterday afternoon, Hon. W.G. Irwin, Mr. T.R. Foster and Hon. J.A. Cummins were appointed as trustees of the property of the company in the interest of bond-holders.

Mr. A.S. Hartwell was appointed attorney to the company during the anticipated absence of the President, Hon. W. R. Castle. Mr. W. P. Toler was appointed Secretary pro tem during leave of absence to Mr. Geo. C. Williams. About three miles of the permanent way are graded. Mr. Dillingham, the contractor, leaves for the coast on business connected therewith, by to-day's steamer. he will order two locomotives of the latest pattern from the Baldwin Works, Philadelphia, which will be delivered in San Francisco at ninety day's notice. In San Francisco he will order fourteen passenger cars up to the most improved standard of suburban trains, and nine freight cars. He hopes to keep his promise of having trains running within a year from the passage of the franchise.

Operationally, Dillingham's first decision was an easy one: standard gauge vs. narrow gauge? Used on long haul railroads across the United States, standard gauge–four feet, eight-and-a-half inches between the rails–was more expensive for every facet of the system. Locomotives and larger and thus the train consumed more fuel. The track was heavier and ran on a wider roadbed. the cost per mile of using standard gauge for OR&L would have been prohibitive, and, realistically, there was no real need for using it.

Distances were not great on Oahu, and the three foot narrow gauge selected by Dillingham was an ideal choice. The five plantations along the line to come, plus the Army's Fort Kamehameha line and the Navy's tracks at Pearl Harbor, all standardized at OR&L's three foot gauge.

But those other trains were "down the line,"as a railroad man might say, for neither the plantations nor the military bases had yet been created. It remained for Dillingham, as the project's contractor, to get his tracks laid in time for the grand opening. Despite what in hindsight we would see as a great investment opportunity, the financing was still tight, and Dillingham–no stranger to going deep into debt–did just that. He sunk much of his own money into the railway-to-be and convinced as many individuals and corporate entities as he could to purchase OR&L stock. Had it not been for his friend Mark Robinson's last minute investment of $30,000 the rails could not have been ordered from Germany, and the project might have stumbled, or worse, collapsed.

Even so, it was touch-and-go during the first few years. Allan Renton, whose forebearers ran Ewa Plantation for two generations, notes that "Castle & Cooke's investment in Oahu Railway almost bankrupted them in the early days."

Meanwhile, Dillingham was raising money and spending it just as fast as it came in to build his railroad. In October 1888 he hired Charles H. Klugel, then 41 and a well traveled civil engineer and land surveyor who had spent the past twenty-one years on various projects in both Mexico and California. Klugel became OR&L's chief engineer, designated to plan the roadbed. To help him oversee the mostly Chinese laborers, Klugel hired young George Denison, who went on to work for OR&L for almost its entire history. As land was acquired, surveyed, cleared and leveled, Denison's track gangs were ballasting the roadbed with coral and spiking 30-pound rail into 'ohai'a ties at a furious pace.

The Saturday July 27, 1889 issue of the Pacific Commercial Advertiser ran the following story under their Hawaii News Summary:

Among the most important works now in progress of rapid construction, is the Oahu Railway to Pearl Harbor, which is already approaching completion, so far as grading is concerned. Eleven miles of this line will have the grading completed in two weeks; and of this length ten miles are already finished. The material for the bridges is already on the ground, and the work of driving the piles has been begun at the larger estuaries of Kahlihi and Moanalua. A few of the bridges on this line will be of considerable length; but , with the present energy being displayed, only a short time will elapse before the gaps in the line will all disappear. Many of the smaller bridges and culverts have been already built. There will be altogether twenty bridges between Honolulu and 'Ewa, of various lengths–from 16 to 300 feet, with an aggregate length of 1250 feet.

Plans have been approved by which the main depot will be placed 180 feet from king street in what is now a fish-pond dividing Oahu prison from the royal stables. A large portion, if not all, of this extensive fish-pond will be filled in without delay, and this substantial and eligible building ground, artificially formed, will become of great value by close proximity to the main depot buildings. The depot itself will be of imposing size and made as ornamental in appearance as convenience and traffic requirements will allow. The grading of the whole division of this line, twelve miles, will be completed within the next month; and the laying of the rails will commence immediately upon their arrival by the bark Deutschland now nearly due from Germany. The progress of this important work has been so rapid during the month of July that we give it first place among works in progress.

The crews were flying. The first ceremonial shovelful of dirt had been turned on March 9, and according to the Advertiser report above, in the 140 days since, ten miles of roadbed was graded and ready for rail. This was by hand labor, using saws and axes to clear the land, and shovels and picks to level it. Frank Dillingham had ordered a steam shovel (which in those days really ran on steam), but it did not arrive until mid-November.

Again in the story, "plans have been approved" for the station. Almost a month later, on August 23, a small ad for proposals to build the main depot appeared in the Advertiser:

––PROPOSALS WANTED–– Sealed proposals will be received up to 12 o'clock noon, September 1st, at the office of the Company on Merchant street. this city, for the erection of a Terminal Depot for the Oahu Railroad and Land Co. Plans and specifications may be seen and all necessary information obtained at the office. The right to reject reserved.


He decided to stay in Honolulu and by the end of 1865 was a clerk at Diamond Hardware, which he bought out for $28,000 in 1869. April 26 in 1869 he married Emma Louise Smith (1844–1920), of a prominent missionary family. She was the daughter of Reverend Lowell Smith and Abigail Willis Tenney.[2] Dillingham turned out to be an astute businessman, and more importantly, was always willing to take risks. In 1879 he started a dairy farm in upper Honolulu, and during the 1880s became increasingly successful. He founded the Oahu Railway and Land Company (OR&L) that began service in November 1889. Dillingham was well liked among Honolulu's various communities, and he included King Kalākaua and Queen Liliʻuokalani as his friends. Although he disapproved of the overthrow of the Kingdom of Hawaii in 1893, he looked favorably on the American annexation in 1898, which he believed would bring long-term stability to the islands. Dillingham spent the rest of his life in Hawaii.

Apart from the OR&L, Dillingham was especially active in sugarcane plantations, including the Olaʻa Sugar Company on the Big Island, and the Ewa and Kahuku sugarcane plantations on Oahu. While the OR&L and these sugar companies were profitable, Dillingham's Big Island railroad, the Hawaii Consolidated Railway (Hilo Railroad) was a financial drain until its destruction by a tsunami in 1946. His Hawaiian Fiber Company, which operated a sisal plantation on the Ewa coral plain in southwestern Oahu, was ultimately also a failure. Nevertheless, Dillingham was one of the major business people in the early years of Hawaii's economic and industrial development.

He died on April 7, 1918 and was buried in Oahu Cemetery. Two days before, James Bicknell Castle, a distant cousin of his wife and a partner in sugarcane plantation ventures, died.[3] His son Walter F. Dillingham (1875–1963) would also become a businessman in Oahu.[4]

His wife Emma Louise Smith Dillingham wrote a book of poetry on Diamond Head.[5] His daughter Mary Emma (known as May) Dillingham married Walter Francis Frear (1863–1948) who became Governor of the Territory of Hawaii 1907–1913.[6] The next governor from 1913 to 1918, Lucius Pinkham, was a Democrat, although he had worked for Dillingham at OR&L 1892–1894 and as manager of his hardware company 1898–1903.[7] Two sons died young, Charles Augustus Dillingham (1872–1874) and Alfred Hubbard Dillingham (1880–1880). Youngest son Harold Garfield Dillingham (October 9, 1881 – December 19, 1971) married Margaret Bayard Smith in 1885 and had 4 children. Youngest daughter Marion Eleanor Dillingham (September 23, 1883 – January 19, 1972) married John Pinney Erdman in 1874 and had five children.[6]


  1. ^ Simpson, Jim Chiddix & MacKinnon (2004). Next stop Honolulu! : Oahu Railway & Land Company 1889-1971 (1st trade ed.). Honolulu, Hawaii: Sugar Cane Press. p. 352. ISBN 0-9706213-1-0. 
  2. ^ Tenney, Jonathan (1904) [1891]. The Tenney family, or, the descendants of Thomas Tenney, of Rowley, Massachusetts, 1638-1890. Rumford Press. pp. 321–322. 
  3. ^ "Correspondence from Hawaii: Death of Three Prominent Sugar Men". Sugar. May 1918. pp. 197–198. 
  4. ^ "Hawaii: Patriarch to a State". Time Magazine. November 1, 1963. 
  5. ^ Dillingham, Emma Louise Smith (1891). Diamond Head. 
  6. ^ a b Frear, Mary Emma Dillingham (1934). Lowell and Abigail: a realistic idyll. Yale university press. p. 307. 
  7. ^ Melendy, H. Brett (1983). "The Controversial Appointment of Lucius Eugene Pinkham, Hawaii's First Democratic Governor". Hawaiian Journal of History 17 (Hawaii Historical Society). pp. 185–208. hdl:10524/373. 

Further reading[edit]