[1] Born on September 13, 1934, Woolsey was raised in Oahu's scenic Manoa Valley three miles East of downtown Honolulu, near the Pacific shoreline and after taking to the water by six, he was swimming competitively by nine.

[3][4] In his youth he met Hall of Fame Coach Soichi Sakamoto, then a Boy Scout master on Maui, who also taught school.

McKinley had a powerful high school swim team of over 20 swimmers that included future Olympic trial competitors.

[10] Not confined to the Hawaiian Islands, Woolsey helped lead his McKinley High School team that year to championships at the M.I.T.

[12] In a year that saw impressive participation in the Olympics by American swimmers from the territory of Hawaii, Woolsey was notably the fifth Hawaiian to make the U.S. swim team.

Other Hawaiian swimmers making the U.S. team that year included Ford Konno, Evelyn Kawamoto, Dick Cleveland, and Yoshi Oyakawa.

[15] At the 1956 Summer Olympics in Melbourne, Australia, Woosley won a silver medal in the 4×200-meter freestyle relay with University of Michigan swimmer Dick Hanley, George Breen, and Ford Konno, another talented native Hawaiian.

[2][18] In the 400-meter freestyle preliminaries, Woolsey placed tenth and did not make the finals, and though American George Breen managed to take the Bronze medal, the event was won by another exceptional Australian, Murray Rose.

[18][21] Maintaining his conditioning, in 1977, at age 32, Woolsey swam a third-place 5:24.70 for the 400-meter freestyle in a United States Masters meet in Hawaii.