Jeannie Chesser was born in Miami Beach and started surfing at South Beach in 1964 at age 14. A year later, she won her first surfing event, the Big Kahuna South Beach Surf Contest. The next year at the Florida State Championships, Chesser placed third behind ECSHOF members Mimi Munro and Kathy Anderson.
She met David Chesser of Hialeah, who also surfed at South Beach, and they married in 1967. Future big wave surfing legend Todd was born a year later. Sadly, David died in a car crash in Miami in 1970, so the Chessers moved to Cocoa Beach and, shortly after, to Hawaii. Jeannie Chesser enjoyed surfing in amateur HSA contests and won a number of events. She placed 4th at the US Championship at Malibu in 1973 and, again, placed 4th at the ISA World Surfing Championship in 1980 in France and 1984 in California. Chesser also won the Hawaii State Surfing Championship in 1983. A second tragedy fell upon Chesser as her son, Todd, lost his life surfing giant outer reef waves on the North Shore in 1997.
Chesser began airbrushing surfboards in the early 70’s for Hawaiian Island Creations and has worked for most of the top shapers and surfboard companies in Hawaii. She is a commentator for the Hawaiian pro events and a WSL qualified judge for the professional men’s and women’s events on the North Shore. Chesser helped create the Hawaii Women’s Surfing Hui in the 1970s along with her best friend, Rell Sunn, and was instrumental in the very first “Menehune Meet,” which they started in Haleiwa in 1975. She was Hawaii’s Senior Female Athlete of the Year in 1984, and received the “Na Wahine Hano Hano O Ke Kai” award from Quiksilver/Roxy in 1998 for “Outstanding Woman in the Field of Watersports.”
Chesser was one of nine amazing women featured in the 2019 documentary, “She is the Ocean.” Chesser still surfs as much as possible and lives by her personal motto, “Surfing is the key to health and fitness.”