Maui couple remembered: Robert Seymour “Lindy” Haʻalilio Sutherland and Cherry Anne Kamalama Waterhouse Sutherland

Robert Seymour “Lindy” Ha’alilio Sutherland — Jan. 27, 1932 – Nov. 10, 2025
Cherry Anne Kamalama Waterhouse Sutherland — April 23, 1935 – Nov. 18, 2025

Lindy was born in Honolulu, Hawaiʻi on Jan. 27, 1932. He was the great grandson of James Campbell and Abigail Kuaihelani Maipinepine Bright Campbell, grandson of Dr. Fred E. Trotter, and son of Muriel Melvia Kuaihelaniahumanu Shingle Sutherland.

Lindy grew up in Honolulu, Hawaiʻi, graduating from Punahou School, as part of the “nifty” class of 1950. As a teenager during World War II, Lindy lived in California, on a cattle ranch, where he spent his free time riding his favorite horse “Black Diamond,” and developed a connection working with animals and a passion for ranching.

Lindy volunteered for the U.S. Marine Corps after graduating from Punahou School and spent time in Korea during the Korean War. Following his tenure with the Marines, Lindy attended Pasadena City College, and Colorado A&M, which he attended on a football scholarship, where he played center for three years. Lindy graduated from Colorado A&M in 1956 and returned to Hawaiʻi to begin his professional career.

Cherry Anne was born in Honolulu, Hawaiʻi on April 23, 1935. She was the great granddaughter of Samuel T. Alexander and granddaughter of John T. Waterhouse, the founder and long-term president of Alexander & Baldwin, Inc., respectively. She was the daughter of Richard S. Waterhouse and Alice Clay Beddhoe.

Cherry Anne spent her early years in Honolulu and Palo Alto, California, and began her life-long passion of riding and caring for horses during this time.

Cherry Anne attended Punahou School, graduating in 1953. While attending Punahou, Cherry Anne would spend time at the Diamond Head Riding Stables near Kapiʻolani Park, where she first met Lindy, who was working at the stables.

She attended Skidmore University after graduating from Punahou School. While at Skidmore, Lindy, with the encouragement of his mother, visited Cherry Anne in New York. They began a lifelong relationship, and Cherry Anne later transferred to the University of Colorado, and then on to Colorado A&M, to be with Lindy.

Cherry Anne and Lindy were married on Aug. 10, 1956. Cherry Anne enjoyed taking care of Lindy and her family, riding her horses, painting, baking, and driving her children and grandchildren all over Maui.

She was a member of Waipuna Chapel, and advocate of Kids Hope USA, where she mentored children attending Kula School. She was an incredible mother, grandmother and great grandmother, always welcoming the family and friends for meals, and was well known for sharing her special cookies with her friends and family.

Lindy’s first job was with Alexander & Baldwin, Inc., in their management trainee program, spending time at various sugar plantations on Oʻahu, the Big Island and Kauaʻi, before formally beginning his tenure at McBryde Sugar Plantation in ʻEleʻele, Kauaʻi.

After 10 years at McBryde, Lindy moved to Maui, where he worked at the HC&S Plantation in Puʻunēnē, and managed the Princess Papaya operations nearby.

In 1975, he “changed horses” and began work at Kaupō Ranch, where his longtime friend, Carl “Soot” Bredhoff was the manager. Lindy drove the 2-hour drive from his home in Kula to Kaupō most days for work returning late in the day. He became involved with the Kaupō community, assisting with protecting archeological sites located on Ranch property, and supporting the community in countless ways.

Lindy learned much from his time at Kaupō with Soot, Leighton Beck, Francis Poouahi and others, and in 1984 took over the responsibilities of operating Kipukai Ranch, on Kauaʻi, following the death of Cherry Anne’s uncle, Jack Waterhouse.

Lindy managed Kipukai Ranch with the assistance of managers including Alex Franco, Greg Friel, Brian Caires, and Robert “Bobby” Ferreira, until its closing in 2005, after which he formed Olumau Angus+, LLC, with Bobby Ferreira, which operated a bull and cow pure breeding business, incorporating artificial insemination, pasture management, and other cutting edge techniques to provide specified qualities and characteristics of cattle for Hawaiʻi’s ranches.

Lindy retired from active ranching in 2010 but continued to provide his time and assistance to the cattle industry for the rest of his life.

In addition to his time ranching, Lindy volunteered his time and services to the local Kiwanis and Jaycees organization, was a long-time member and President of the Saint Anthony School Board, and spent many weekends as a referee for the Maui Youth and Adult Soccer teams from 1975 through 1990.

Throughout his life, Lindy sought to provide his time and services to his community, supporting his neighbors and friends, and was always ready and able to assist in any way, with Cherry Anne as his primary support, always ready to assist, providing a smile, cookies, or anything else needed for the effort.

He and Cherry Anne supported many children and their families with assistance in tuition for school, life, and any other challenges. They supported the Montessori School of Maui in the construction of the campus on Baldwin Avenue, where Cherry Anne was a member of its Board, and contributed to many charitable programs supporting Hawaiian culture and programs.

Lindy had a kind ear, a twinkle in his eye, and a passion to assist his community and friends. Cherry Anne and Lindy took on many challenges, volunteering with each other throughout the years for various programs, and together, sought to improve the welfare of the Kauaʻi and Maui communities. They will both be deeply missed.

Lindy and Cherry Anne requested it be stated that they appreciated and acknowledge all the love, care and support they have received over the years from their family and many friends, as well as the care they received recently from Jason and Donna Piano, and their daughter Jaennah.

Lindy passed away peacefully on Nov. 10, 2025, followed by Cherry Anne on Nov. 18, 2025, at “Olumau,” their home in Kula, Maui, Hawaiʻi.

Lindy’s parents, and siblings Fred E. Trotter, III, Alicia “Auwe” Sutherland Morris, and Jonathan Ross Sutherland, predeceased Lindy, and Cherry Anne’s parents and sister, Dicksie Lee Waterhouse Sandifer predeceased Cherry Anne.

Lindy and Cherry Anne are survived by their sons, Clay (Susan) and Kurt (Lisa) Sutherland, and daughter, Carey Lee Sutherland, as well as their grandchildren Lindsay, Emmalia, Anuhea, Mikayla, Joshua, Tyler and Kailie, and 10 great grandchildren.

A private memorial and burial will be held by the family. Donations in Lindy and Cherry Anne’s memory may be made to Punahou School (808-944-5711), Hospice Maui (808-244-555), the Maui Memorial Medical Center Foundation (808-242-2630), or other community charity of choice.

Aloha no, a hui ho, me ke aloha palena ‘ole.

Note: The above obituary was provided by family.