Saturday Briefing

By Dr. Richard Kelley

It was exactly 80 years ago this month, September 1929, that our founders, Roy and Estelle Kelley, arrived in Hawaii.

1929 was certainly a landmark year for my parents. As recounted in John McDermott’s book, Kelleys of the Outrigger, Roy was working as a staff architect for Ed Doheny, patriarch of the oil-rich Los Angeles family, and his son Ned, who were developing a residential subdivision next to the then-barren beach lands near San Juan Capistrano, California.

More than just drawing plans, Roy also helped with the weekend auctions when prospective buyers were bused into the project from Los Angeles. Roy even did a bit of shilling during the auctions and admitted to occasionally calling out something like, “Don’t sell lot number 44. I have a buyer!” to generate excitement and spur sales.

Ned Doheny was murdered in February 1929; however, the project still seemed capable of going forward. Roy married his sweetheart Estelle in May of that year, and the couple briefly honeymooned by driving up the west coast to Portland, Oregon. They returned and moved into a small house Roy was completing in the subdivision.

However, with the death of his son and the weakening economy weighing on his mind, Ed Doheny closed down the San Juan Capistrano project in mid-summer 1929.

Roy could not find a new job in the area, but in late August, a Los Angeles friend told him that an architect in Honolulu, the renowned C. W. Dickey, was looking for a draftsman. Roy and Dickey exchanged cables, Dickey made a job offer, and four days later, Roy and Estelle were on a boat headed for a new life. The parents of both thought their children were completely out of their minds!

On the morning of September 13, 1929, the steamer City of Los Angeles docked in Honolulu Harbor. Roy (age 24) and Estelle (almost 23) disembarked and began a new chapter in their lives.

Honolulu was a sleepy city then, serving the needs of Hawaii’s plantation economy. There were only 22,000 visitors that year. Most stayed in Waikiki at the Moana or Royal Hawaiian hotels. Business travelers found rooms at the Alexander Young Hotel at the corner of Bishop and King streets. Sailors found accommodations near the waterfront on Hotel Street.

Roy immediately dove into a pile of work that had accumulated on the drafting tables of the Dickey firm. Estelle worked as a legal secretary. They saved and soon bought a house at the corner of Seaside and Kuhio Avenues in Waikiki, which was then a suburban neighborhood.

In 1938, they built a new combination home and office on the other side of Kuhio Avenue, and Roy opened his own architectural firm. They added small, wood-frame apartment buildings on nearby lots and rented the units out to supplement their income.

Following World War II, they began renting the apartment units on a daily basis, serving guests breakfast on the lawn under the kiawe trees with the help of their three children – my sisters and I – running what would today be called a bed and breakfast operation. That led to the building of their first Waikiki hotel, the Islander, in 1947.

Since then, the hotel operations of what is now called Outrigger Enterprises Group have spread across all the major Hawaiian Islands, in selected areas in the continental U.S., across the Pacific to Australia, Fiji, Indonesia, Thailand, and, one day soon, China.

These are fast-moving, exciting times, but it is good to stop and remember that it all began 80 years ago when the City of Los Angeles arrived in Honolulu with Roy and Estelle Kelley on board.