Richard R. “Doc” Kelley, the second-generation leader of what had long been Hawaii’s largest locally owned and operated hotel chain, has died.
The former longtime chief executive of Outrigger Hotels and Resorts, who left a job as a Queen’s Hospital doctor to join the family tourism business, was 88.
Kelley died Thursday in Denver, where he had lived with his wife, Linda, for 29 years. For two decades he battled Parkinson’s disease, though that didn’t keep him from recently finishing a partially autobiographical book.
Family members described Kelley as arguably the single-most consequential figure in the local hospitality industry’s development over four and a half decades, during which he helped lead Outrigger through dramatic expansion along with tourism in Hawaii.
“He certainly built quite a legacy of hotels,” said John Monahan, president and CEO of the Hawaii Visitors and Convention Bureau. “They were just absolutely foundational in helping build the visitor industry in Hawaii.”
Kelley was the eldest son of Outrigger founders Roy and Estelle Kelley, pioneers who got into the business in 1947 by building the five-story, 50-room Islander Hotel on Seaside Avenue in Waikiki.
Like most members of the Kelley family, Richard Kelley grew up in the business and started with entry-level work that included hauling luggage up several flights of stairs and serving pineapple juice to guests.
Later, Kelley graduated from Stanford University with straight A’s, after being challenged by dyslexia and admittedly not being a great student at Punahou School, then earned a Harvard Medical School degree in 1962 that led to him becoming a pathologist at Queen’s, where he examined causes and effects of diseases.
The Outrigger founders, however, pulled their eldest son back into their hotel business, where he became president and CEO in 1971 after leaving medicine in 1970. He made the move to help his parents run the company a few years after they developed the beachfront Outrigger Waikiki hotel on land between the historic Moana and Royal Hawaiian hotels.
In the book “Kelleys of the Outrigger” by John McDermott, Richard Kelley explained that Outrigger was struggling with management, and he found himself not being able to focus on his tedious medical work because he was thinking about hotel operations.
“That’s when I moved into the big chair,” he recounted for the book.
Roy Kelley kind of retired in 1975, though Richard Kelley didn’t assume full control of Outrigger until the late 1980s.
A similar gradual transition from the second generation to the third took place with Richard Kelley’s son-in-law David Carey joining the company in 1977, becoming president in 1988 and then CEO in 1994. Richard Kelley remained chairman for years, and was chairman emeritus when the family sold Outrigger in 2016 to Denver-based KSL Capital Partners LLC for an estimated $900 million.
During Richard Kelley’s leadership at Outrigger, the company graduated from a mom-and-pop business, modernized operations and expanded beyond Waikiki greatly with properties initially on the neighbor islands and then to places including Tahiti, Fiji, New Zealand, Australia, the mainland, Southeast Asia and even Mauritius and Maldives in the Indian Ocean.
Kelley also was a champion for developing a convention center in Waikiki, and was known for sharing wisdom and helping people in many ways.
Kitty Yannone, owner and CEO of local public relations firm CommPac, which long represented Outrigger, recalled a time in 1984 when she was working on an account for the Ronald McDonald House, where parents can stay while their children undergo medical procedures. Kelley heard about the planned charitable project and offered to donate hotel rooms until the facility opened in 1987. Then, after Ronald McDonald House opened, Kelley continued to donate rooms for nearly 30 years to accommodate overflow demand that sometimes amounted to 2,000 to 3,000 nights a year.
“Thousands of people stayed there,” Yannone said. “The generosity was typical of the Kelleys. It was a massive thing, what they did.”
Kelley also aimed to treat employees like family as his parents did, and every week for 40 years he produced a written briefing for workers in which he shared items that included recognition of employee milestones or accomplishments, as well as industry information that could include policy issues and industry developments.
These “Saturday Briefings” over time became something that Kelley shared with others who wanted to be on his distribution list, including government officials, business people and the media.
Monahan, who ran kamaaina department store chain Liberty House before joining HVCB, was a subscriber.
“I read his bulletin religiously,” Monahan said, adding that Kelley even contacted him during a difficult time, as Liberty House was working through bankruptcy, to offer encouragement, wisdom and hope that a local company would survive.
“I have such a warm spot in my heart for him,” Monahan said.
Kelley also instilled the family’s “Outrigger Way” principles that involved employees understanding and sharing Hawaiian culture, history and values, in part to teach visitors to be good guests.
Chuck Kelley, a doctor and son of Richard Kelley who worked for Outrigger from 2001 until the 2016 sale, said his father was an ultimate people person.
“He really, really enjoyed working with people,” Chuck Kelley said. “That is what really drove him in his personal and business life.”
Chuck Kelley said his father moved to Denver in 1993 to see what it would be like for perhaps a short period, but instead settled there and for many years regularly commuted to Hawaii for work.
When the Kelley family sold Outrigger, the company operated, owned and managed 37 hotels, condominiums and vacation resort properties conveyed to KSL.
Chuck Kelley said his dad never retired, essentially shifting from Outrigger’s chairman emeritus in 2016 to a director of a new family business, Seaside Ohana Investments Inc., formed to manage assets produced from Outrigger’s sale.
On a more personal side, the Kelley family described Richard Kelley as someone who enjoyed puns, naughty limericks and talking story. They also said their deeply loved patriarch was an all-around waterman who surfed, sailed, fished and once won an award for the smallest fish caught in a billfish tournament.
One of Kelley’s last feats in life was finishing a book he had been working on for nearly 40 years. “Paddling the Outrigger: Inspiration and Insights from the Journey of a Lifetime” was published last year by Bess Press.
Kelley is survived by his wife; sister Jean Rolles; children Kathryn Carey (David), Chuck Kelley (Jenny), Linda Jane Kelley, Elizabeth “Bitsy” Kelley (Greg), Colleen Kelley Heyer (Judd), Christopher Kelley and Anne Marie Kelley Brown (Matt); 15 grandchildren and 12 great-grandchildren. He was predeceased by his first wife, Jane Zieber Kelley, and his sister Patricia Kelley.
Memorial services in Honolulu and Denver are being planned, but details have not yet been finalized.
