Business
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. 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 sugar plantations, including the Olaʻa Sugar Company on the Big Island, and the Ewa and Kahuku sugar 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 died, a distant cousin of his wife and a partner in sugar plantation ventures. His son Walter F. Dillingham (1875–1963) would also become a businessman in Oahu.
His wife Emma Louise Smith Dillingham wrote a book of poetry on Diamond Head. His daughter Mary Emma (known as May) Dillingham married Walter Francis Frear (1863–1948) who became Governor of the Territory of Hawaii 1907–1913. 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. Two sons died young, Charles Augustus Dillingham (1872–1874) and Alfred Hubbard Dillingham (1880–1880). Youngest son Harold Garfield Dillingham (October 9, 1881–?) married Margaret Bayard Smith in 1885 and had 4 children. Youngest daughter Marion Eleanor Dillingham (September 23, 1883–?) married John Pinney Erdman in 1874 and had five children.
Read more about this topic: Benjamin Franklin Dillingham
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