For a free drink for you and one guest at the CYC bar (courtesy of Ken Johnson):

Questions:

Which CYC member was the first to represent the USA in an Olympics sailing event and which CYC member most recently represented the USA in an Olympics sailing event?

As tie-breakers, in what years and in what boats?

Answer:

The first CYC members to participate in an Olympics sailing event were Alan Holt and Dick Gates, sailing the Star “Ariel,” built by Alan, in the 1972 Olympics in Kiel-Schilksee, Germany.

The most recent CYC sailing Olympians were Jonathan and Charlie McKee, sailing a 49er in the 2000 Olympics in Sydney, Australia, winning a bronze medal. 

Although no one got both answers (which, by the way, could be found on page 37 of the 2020 CYC Navigator), congratulations (and a free drink for him and a friend) to Rear Commodore Pat Dore