Posted on: Sunday, July 2, 2006

Benjamin Dillingham

By Will Hoover
Advertiser Staff Writer

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It was a broken leg that led to Hawai'i sugar baron Benjamin Dillingham living in the Islands.

And although he did more than anyone to open O'ahu and other Islands up to agriculture and make sugarcane irrigation a reality, Dillingham's claim to fame will remain tied to the railroad he built in 1889 that made agriculture possible.

That freight line — known early on as "Dillingham's Folly" — eventually included exclusive passenger service to a magnificent and secluded North Shore hotel around which the town of Hale'iwa would be built.

Like other Hawai'i commercial pioneers, Dillingham had experienced many travels and adventures before reaching O'ahu in 1864 at the age of 20. The visit was intended to be a brief stopover.

Dillingham was first officer aboard the bark Whistler. While ashore here, he fell from a horse and broke his leg. The prolonged recovery ended his nautical career but led to his becoming Hawai'i's railroad tycoon.

In time, Dillingham would expand his sugar and railroad operations to Neighbor Islands, although he severely overextended his credit in the process.

Fortunately for him, his successful and business-savvy son, Walter Dillingham, took over the financial responsibilities of his father's enterprises.

The elder Dillingham remained president of the Oahu Railway & Land Co. until his death in 1918.



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