Eight Bells: Roy Cundiff

Roy Sharp Cundiff, 84, well known at the front of most race fleets, passed away April 30, 2026 at home in Long Beach, CA.

Born in Inglewood, California, his father worked as an aerospace engineer, and Roy and his younger sister, Thelma Cundiff (Sorenson), moved frequently throughout Southern California, spending much of his childhood in Mojave and later in Lancaster.

After high school, Roy studied engineering at UCLA for three semesters before joining Rocketdyne, where he tested 200,000-pound-thrust rocket engines for the Saturn 1A booster. It was there that his passion for sailing began.

His boss, Tony Gaechter, who became a lifelong friend, bought a Cal 24 and told Roy it was time to learn to sail. During lunch breaks at Rocketdyne, colleague and friend Bob “Bumpy” Smith shared his extensive sailing knowledge, teaching Roy everything from tying knots to setting a spinnaker.

Four years later, Roy decided to make sailing the focus of his career. He joined Stan Miller Yachts as a rigger before moving into sales, and then briefly at Jensen Marine before becoming a sales manager at North Sails.

A skilled tactician and helmsman, he was in high demand. While at North Sails, he would even crew for customers if their new sail orders were large enough. For more than 50 years, Roy raced with teams around the world.

A highlight was winning the 1978 Quarter Ton Cup in Japan aboard Magician V. He was also a regular participant in the Ensenada, Transpac, and even Germany’s Kiel Week races, sailing on well-known boats including Windward Passage, Ragtime, Warlock, Merlin, Sunset Boulevard, and Ruben.

Wet Wednesdays and Thirsty Thursdays were summer staples, and he devoted much of his time to his Cal 27, Finale, and later, Grand Finale.

One of Roy’s grandest adventures was supervising the construction of Peter Powell’s 62-foot Sunreef catamaran, Blaze II, in Gdańsk, Poland and then cruising aboard her from Poland to Portugal. He also joined Tony Gaechter on several charter cruises in Turkey and Greece.

Roy was also an adept draftsman who briefly worked for architect Barry Berkus. He brought that same talent to designing several sailboats. His technical skill and creativity complemented the sailing expertise that would shape his long career.

Flying was another of Roy’s passions. It began in the early 1970s at a small airport in Perris, California, where weekend glider lessons led to R1’s success on the competitive soaring circuit, including a national title in 2003. He also earned his private pilot’s license and owned a 1983 Cessna 185F bush plane for many years.

Whether spending weekends at Catalina Island on the boat, taking ski trips to Mammoth, or enjoying lively Summer Bummer parties at the Seal Beach house with Pete and Ann Ebeling, Roy was always ready for the next big adventure.

While playing trumpet in the Antelope Valley High School band, he met his first wife, Ann Stivers (Cumiskey). They married in July 1961, and their daughter, Joyce Cundiff (Pritchard), was born the following year.

Roy married Cheri Locken in January 1981. During their 20 years together, they traveled extensively, including to Japan and throughout Europe. Together they raised Buster and Riley, their big-hearted yellow Labradors, and remained good friends throughout his life.

In 2005, Roy married Carol Scott, a fellow private pilot. They remained together until his passing, sharing a love of travel, flying, sailing and even rockets as Carol worked at Jet Propulsion Laboratories. The couple spent several years living beside a lake in Corsicana, Texas, and between moves even lived in an aircraft hangar in California City.

For nearly 30 years, Roy faced the devastating effects of metastatic prostate cancer. Despite the pain and physical limitations it caused, he remained a positive force wherever he went. Rarely seen without a Diet Coke or Bud Light in hand, he made friends easily and generously shared his time and knowledge.

His impact on others cannot be measured, and no single page could fully capture the countless memories Roy created or the accomplishments of his remarkable life.

A Celebration of Life is planned for October 25 at 1300 at the Alamitos Bay Yacht Club in Long Beach, CA.