Richard Chester Moss

Richard was born on May 8, 1947, in Utulei, Tutuila, American Samoa, to Chester Moss and Amanda Moss, both of whom preceded him in passing. A proud island boy at heart, Richard carried his roots with him throughout his life—living by the spirit of connection, resilience, and aloha wherever he went.

As a young child, Richard moved with his family to Illinois in 1948, and later to Southern California, where he spent much of his youth. In 1966, he answered the call to serve his country by enlisting in the United States Navy. He completed boot camp at the San Diego Naval Training Center and went on to serve honorably aboard the USS Barb (SSN-596), a nuclear submarine stationed at Pearl Harbor. Rising to the rank of Fire Control Technician First Class (FTG1), Richard served with dedication until his honorable discharge in 1972.

Following his military service, Richard pursued higher education, earning his Bachelor’s degree in Economics from the University of California, Santa Cruz, and later completing his MBA at Cornell University. He returned to Santa Cruz, where he built a meaningful career dedicated to service and community. Over the years, he worked with United Way of Santa Clara and several school districts as their assistant superintendent of business services, including Soquel Unified School District, San Lorenzo Valley Unified School District, and Santa Cruz City Schools, dedicating over 30 years to supporting students and families and making a lasting impact.

In 2009, Richard retired to Maui, where he embraced the island lifestyle he always cherished. He was an active member of his community, volunteering his time with the VFW and the Pacific Whale Foundation. He found joy in life’s simple pleasures—watching baseball (especially cheering on the SF Giants), fishing, going to the gym, and taking peaceful walks along the beach.

Richard loved spending time with family and friends, whether it was sharing meals at Three’s Bar & Grill, riding his motorcycle to Lahaina for Sunday breakfast, or stopping by Sugar Beach Bakery for his favorite morning malasada. He stayed closely connected with those he loved, always offering a listening ear, steady support, and genuine care.

He will be remembered as a loving, caring, and kind man—hardworking, dependable, and easygoing. Richard was deeply devoted to his family and would do anything for those he loved. His strength, resilience, and quiet generosity touched many lives. He was “born an island boy, always an island boy.”

Richard is survived by his daughters, Maxi Moss, Brandi Cunningham, and Ginger Cruz; his sons-in-law, James Woods and Dan Cunningham; and his granddaughters, Jean Cunningham, Morgan Cunningham, and Noelle Cunningham. He is also survived by his brother, Ronald Moss; his sisters, Rose White, Marilyn Moss, and Mary Moss; his former wife and beloved lifelong family friend, Brenda Moss; along with many nieces, nephews, and a multitude of Samoan cousins who will forever cherish his memory.

A 1-hour visitation honoring Richard’s life will be held on Tuesday, April 7, 2026, from 11:00 a.m. to 12:00 p.m. at Norman’s Mortuary, located at 105 Waiale Road in Wailuku. Burial with military honors will follow at 1:00 p.m. at Maui Veterans Cemetery in Makawao. The VFW will be hosting a celebration of life in honor of Richard from 4:00 p.m. to 8:00 p.m. at VFW Post 3850 located at 1136 Uluniu Rd, Kihei, HI 96753.

The family would like to extend their heartfelt gratitude to Richard’s dear love, Ingrid Natzke, the ICU nursing staff and doctors at Maui Memorial Medical Center, his fellow VFW members, his friends at Kalama Heights, and all friends and family for their prayers, love, and support during this time.

Richard’s life was one of service, strength, and love—a legacy that will live on in all who knew him.

Aloha ‘oe ~ Tofa Soifua ~ A hui hou