Obituary: Dr. Richard Kelley, 88, grew Outrigger into a leading Hawaii hotel brand

Dr. Richard Kelley, who grew Outrigger Hotels and Resorts into one of Hawaii’s largest hospitality players over the course of more than four decades, died on Feb. 24, after a 20-year battle with Parkinson’s Disease. He was 88.

Under Kelley’s leadership, the Outrigger empire enjoyed a period of significant expansion, venturing far beyond its home base of Waikiki to include hotels, resorts and condos across Kauai, Maui and the Big Island of Hawaii and setting the stage for international growth.

“We are deeply saddened to learn of the passing of Dr. Richard R. Kelley,” Jeff Wagoner, president and CEO of Outrigger Hospitality Group, said in a statement. “Dr. Kelley was an inspiration for so many, and his legacy of ‘The Outrigger Way’ — caring for guest, host and place — continues to be the foundation of our corporate culture today.”

Joining the family business

Kelley was the son of Outrigger founders Roy and Estelle Kelley, who built their first hotel in 1947. Initially, Richard Kelley embarked on a medical career, graduating from Harvard Medical School in 1962. After a stint as a practicing physician, he later joined the family business, taking the reins as Outrigger’s president and CEO in 1971.

By 1973, the Outrigger brand had grown from a single property — the Outrigger Waikiki, built in 1967 — to a total of five Outrigger-flagged Waikiki hotels. In 1986, after a series of acquisitions and brand consolidations, the chain’s portfolio had grown to more than 7,000 rooms, making it a leader within the Hawaiian hospitality sphere, and in 1989, the company added its first property outside of Waikiki, the Royal Waikoloan Hotel on the Big Island.

By the 1990s, the company had begun eyeing international opportunities, eventually making its first foray outside the U.S. with the addition of the Outrigger Marshall Islands Resort in 1996.

Kelley served as Outrigger’s president until 1988 and as CEO until 1993.

He remained chairman of the board until 2011 and served as the Outrigger’s chairman emeritus until the company was sold to KSL Capital Partners in 2016.

Shaping Hawaii tourism

In addition to building the Outrigger business, Kelley is credited with playing an integral role in helping shape Hawaii’s travel industry, spearheading a successful push to create a convention center in Waikiki, which opened in 1994. He was also known for his lobbying efforts to help boost state tourism funding and worked in tandem with the World Travel & Tourism Council to underwrite several studies detailing tourism’s significant impact on the Hawaiian economy.

Kelley was also a published writer, authoring the partly autobiographical book “Paddling the Outrigger: Inspiration and Insights From the Journey of a Lifetime.”

Today Outrigger Hospitality Group comprises the flagship Outrigger brand as well as the midprice Ohana Hotels by Outrigger flag and the Hawaii Vacation Condos by Outrigger business. The Outrigger portfolio currently spans more than 20 hotels, resorts and vacation condo destinations throughout Hawaii, Fiji, Thailand and Mauritius.

Kelley is survived by his wife, Linda V. Kelley; his sister, Jean Rolles; and his seven children as well as 15 grandchildren and 12 great-grandchildren.

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