A captain of real estate and finance in Hawaii died last month, leaving a legacy that includes guiding a trust and a company that were among the biggest in the islands where the lineage of Paul R. Cassiday Sr. reached back 205 years to a close adviser of King Kamehameha I.

Cassiday was a top executive with Amfac Inc., one of Hawaii’s “Big Five” companies during the sugar plantation era, before serving as a Campbell Estate trustee from 1978 to 1998.

He also was part of a family tree laden with well-known Hawaiian and kamaaina branches that once owned around 2,400 acres of land in East Oahu.

Cassiday died Sept. 9, a month shy of his 93rd birthday.

According to a family member, Cassiday died in his sleep at home two weeks after being diagnosed with an aggressive brain cancer that was revealed only when doctors checked the nonagenarian for signs of a head injury in connection with a fall following a dentist’s visit.

“He slipped away quietly, and will be greatly missed,” said son “Ricky” Paul R. Cassiday Jr., who noted that his father was surrounded by family for two weeks of hospice at home and enjoyed the constant attention that he likened to a party.

Colleagues said they lost a dear friend who was not only a highly regarded businessman, but also a kind person with a storied family history.

Cassiday was born in 1928 on what was then known as Niu Ranch in East Honolulu.

The ranch was connected to his mother’s side of the family descended from British sea captain Alexander Adams, who arrived in Hawaii in 1816 and became an adviser to Kamehameha I.

Adams helped create the Hawaiian flag and commanded the king’s naval fleet in operations that included developing a sandalwood trade with China and collecting customs duties from foreign vessels docking in Hawaii.

As a reward for his serv­ice, Adams received land that included the roughly 2,400-acre Niu tract between Wailupe and Kuliouou, and his descendants became early residents of the area who made names for themselves and contributions in the community over many decades.

For instance, Cassiday’s maternal grandfather and son of Adams, Charles Lucas, co-founded the Lucas Brothers construction company, which helped build Iolani Palace and Waikiki’s famed Moana hotel.

The Ranch House restaurant that operated for more than 40 years in Aina Haina, until 1987, was founded by other Lucas family members.

Polynesian navigator Nainoa Thompson and late auto dealer Jimmy Pflueger also are relatives on the Adams family tree.

The paternal side of Cassiday’s family in Hawaii began during World War I when his father, Col. Benjamin Buckles Cassiday, was stationed on Oahu with the U.S. Air Force Signal Corps.

Because of his father’s military service, a young Cassiday attended three grade schools: Punahou, followed by St. Albans School in Washington, D.C., and then Culver Military Academy in Indiana.

Cassiday earned an economics degree from Stanford University and returned to Hawaii in 1950 to start a family with first wife Nancy Bryan, who later married Time magazine editor and philanthropist Henry Luce III. Cassiday later married Fredrica “Ricki” Cassiday.

As a young college graduate, Paul Cassiday joined Amfac, or American Factors, as an insurance trainee and rose to become the first president of Amfac Financial Corp., which at the time was the largest industrial loan company in Hawaii. He also taught risk analysis at the University of Hawaii.

During his time at Amfac, Cassiday helped put sugar plantation lands into resort use, including the creation of Kaanapali on Maui and Princeville on Kauai, as part of a major transition for the local economy.

Howard Hamamoto, a retired Amfac Properties president, called Cassiday an expert in finance and real estate who had a kind management style.

“He was one of the most decent, considerate people I’ve ever known,” Hamamoto said. “He never said a cruel word about anybody. I miss him very much.”

Cassiday was chairman of Amfac’s asset management group in 1978 when he left the company to become one of four trustees overseeing assets for Campbell Estate, which included 80,000 acres of land in Hawaii, for the benefit of descendants of Scottish seaman James Campbell.

Clint Churchill, a former Campbell CEO and trustee, said Cassiday helped lead the trust through some of its biggest changes, including plans to turn former sugar cane fields into Oahu’s “second city” of Kapolei, and reinvesting proceeds from Hawaii land sales in mainland real estate that became worth billions of dollars.

Churchill said Cassiday’s command of finance and risk were especially valuable because creating Kapolei had to be wholly financed, given that the trust required all estate earnings be distributed to beneficiaries.

“That was a huge undertaking,” Churchill said about developing infrastructure along with an initial shopping center and office building to get Kapolei going.

Cassiday also was involved in his own family real estate endeavors. He and four relatives owned a tract of hillside land that developers turned into the Hawaii Loa Ridge subdivision in the 1980s, and he oversaw a family industrial park investment in California.

After reaching the Campbell trust’s mandatory retirement age of 70 in 1998, Cassiday spent time serving on numerous boards and helped manage the Mary Lucas Trust, which held much of the family wealth largely generated initially in the 1970s and 1980s when land was sold under leasehold Niu Valley homes developed in the 1960s.

Cassiday is survived by his wife, son, daughters Lindsey Cassiday-Chang and Brooke Klein, five grandchildren and a vast extended family. He is predeceased by son Cochran Bryan Cassiday and brother Benjamin Buckles Cassiday Jr.