Oscar Chalupsky

Oscar Chalupsky is a surf ski paddler recognized for a career spanning more than four decades in open ocean racing. Chalupsky is a twelve-time World Molokai Surfski Champion, first winning the 30-mile open-ocean race from Molokai to Oahu, Hawaii, and reclaiming the title across three decades. At age 15, he made history at the South African Surf Lifesaving Championships by becoming the first person to win both the junior and senior Ironman titles on the same day. Chalupsky later became the youngest canoe Springbok in South African history and captained the South African paddling team at the Barcelona Olympic Games, competing in the K-4 1000m event.

Chalupsky’s achievements include claiming his twelfth Molokai title at age 49, 29 years after his first win, demonstrating longevity and mastery in surf ski paddling. Beyond his athletic career, Chalupsky co-founded Epic Kayaks, contributing to the growth of open ocean ski paddling equipment, and served as CEO of the Surfski division at Nelo Kayaks. He also established Chalupsky & Associates, a financial investment company, and was a founding member of Citadel Investment Services in South Africa.

Chalupsky was diagnosed with multiple myeloma, an incurable bone marrow cancer, and shared his treatment journey—including radiation, chemotherapy, and a bone marrow transplant—publicly on social media. He continues to paddle and compete while supporting others through the Multiple Myeloma Fund South Africa, which assists patients with treatment costs.

Chalupsky’s memoir, "No Retreat, No Surrender," written with Graham Spence, details his experiences from surf lifesaving to Olympic competition, world championships, and his battle with cancer. The book includes lessons from sport, business, and personal resilience. Chalupsky speaks to audiences worldwide, sharing insights on mental toughness, endurance, and overcoming adversity in both sports and life.