John “Jim” Beresford Kilroy was born on May 1, 1922, in Ruby, Alaska, to George and Rowena (nee Lewis) Kilroy. George Kilroy was an Irish immigrant, gold miner, and gambler. In 1925, George lost the family fortune, and Rowena decided to move the family to California when Kilroy was three years old. In 1930, George left the family, and Rowena, Kilroy, and his siblings worked multiple jobs to support themselves. Kilroy mowed lawns, sold newspaper subscriptions, repaired bicycles, and worked in restaurants.

Kilroy graduated high school at 17 and started studying engineering at Santa Barbara State College before he dropped out the following year. In 1940, he was offered a job at Douglas Aircraft and assigned to work in El Segundo, where the SBD Dauntless Navy Diver Bomber was designed and built. Kilroy climbed the ladder at Douglas Aircraft and eventually became the Douglas Aircraft Inspection Representative to the National Aircraft War Production Council. Kilroy studied aerodynamics and plane construction for two years at the Western Flying Training Command in Santa Ana. In 1944, Kilroy began active duty in the US Army Air Corps Reserve, giving him first-hand flying and training experience. After WWII, Kilroy started working in commercial real estate, founding Kilroy Industries in 1947. By the late 1950s, Kilroy had a reliable team so he could delegate more business tasks, which allowed him to focus on outside interests.

Kilroy decided to take up sailing. He had done surfing before the war and had learned to fly during the war. Surfing, flying, and sailing all involve fluid dynamics, aerodynamics, and hydrodynamics, which fascinated Kilroy. He found that sailing was “much more complicated than flying…and much more rewarding.”

In the early 1950s, Kilroy bought a 46-foot Island Clipper sloop named SERENA. It was a good cruising boat but was only okay for racing. In 1956, Kilroy bought the TASCO II, a 50-foot fractional-rigged yawl sailboat designed by Sparkman and Stephens. He renamed it KIALOA, which roughly translates to “long white canoe” in Hawaiian. Kilroy modified the yacht to reduce its weight and prepare it for racing.

Kilroy went on to own and race five maxi boats, all named KIALOA, from 1956-1989. The KIALOA boats were at the forefront of many advances in yacht design, construction, crewing, and technology. Kilroy used his engineering and flying experience to improve his boats.

Kilroy and his all-amateur crew had great success over the years, including winning the 1969 Transatlantic race and setting the record for the fastest Sydney- Hobart race in 1975. The KIALOAs raced all around the world, and the crew adopted the WWII saying, “Kilroy was here.” After retiring from racing in 1989, the Kilroy family continued to use the KIALOA III to cruise around the world.

In 2012, Kilroy published his autobiography KIALOA US-1: Dare to Win in business, in sailing, in life. The National Sailing Hall of Fame inducted Kilroy in 2014. He died in 2016 at the age of 94.