Born in Berkeley, California,[1] Webster won his first collegiate diving title for Santa Ana Junior College, a school that did not have a pool.

[2] While at Santa Ana, Webster trained off a board in Olympic champion Sammy Lee's backyard sand pit.

[2] In 1957, Webster led the Santa Ana Dons to second and third-place finishes at the conference and state swimming and diving competitions.

The margin of victory between Webster and silver medalist Tobian was less than one-third of a point—the narrowest in Olympic history.

[4] He was only the second diver to win the platform event in consecutive Olympic games, after his coach Sammy Lee accomplished the feat in 1948 and 1952.

Webster won every tower diving competition he entered from 1960 to 1964, including a gold medal in the 1963 Pan American Games in São Paulo, Brazil and the U.S. National AAU championships from 1960 to 1964.