Penny Simmons

Born and raised in Bermuda, it was only natural that Penny Simmons would spend his life sailing. Simmons sailed in his first official race when he was 13-years-old where he came first in the Cup Match Regatta. It was the beginning of a prolific career on the water that saw him win 20 national titles in the Snipe class in the 1950s alone. In recognition of his talent Simmons was named the Bermuda Athlete of the Year in 1956 when he was still only 18.

Simmons made his first of four Olympic appearances at the 1964 Tokyo Games, finishing fifth in the Dragon with Kirk Cooper and Conrad Soares. Three years later he and Richard Belvin won bronze at the 1967 Pan American Games in the Snipe. Simmons made three more appearances at the Olympics, sailing in the Dragon at the 1968 Mexico City and 1972 München Games, with his final outing coming at the 1976 Montréal Games in the 470 class with Larry Lindo. He was again named the Bermuda Athlete of the Year in 1979. Simmons won the International One Design World Championship on six occasions between 1985 and 2005, and was inducted into the Bermuda Sports Hall of Fame in 2009.