Joseph “Nappy” Napoleon paddled in his first Moloka‘i Hoe, the annual long-distance open ocean canoe race from Moloka‘i to O‘ahu, at the age of 17 in 1958. He has competed in the 41-mile race from Hale O Lono Harbor on Moloka‘i to Waikiki Beach every year, and on October 7, 2007, Nappy completed his 50th consecutive crossing.

His milestone crossing was very special as the feat was accomplished as a member of the Anuenue Canoe Club team, and his crew included his five sons; Joey, Aaron, Darryn, David and Jonah; and grandsons Josh, Sepa and Koa. In the 50 years of racing the Kaiwi Channel, Nappy was on six championship teams in 1958, 1961, 1966, 1969, 1972 and 1973.

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