bad look for US Olympics.
sure, the Russian women turn into men... but we're the first country to have a male Olympian become a woman.
Maybe not. The first mandatory gender determination tests for women in the Olympics were instituted in 1950. This continued through the 1960's. In fact this issue first came up as early as 1932.
Perhaps the earliest known case is that of Stanisława Walasiewicz (aka Stella Walsh), a Polish athlete who won a gold medal in the women's 100 m at the 1932 Summer Olympics in Los Angeles, but who after her death in 1980 was discovered to have had partially developed male genitalia.
Professional tennis player Renée Richards, a transsexual woman, was barred from playing as a woman at the 1976 US Open unless she submitted to chromosome testing. She sued the United States Tennis Association and in 1977 won the right to play as a woman without submitting to testing.
Bruce Jenner has been a career celebrity. Other than early achievements in the Olympics, what besides being a celebrity has he ever accomplished besides maintaining a position in the public's eye. The obvious downside of this is that he's given up all privacy even in matters which should concern no one else but he and his family and friends. It's the life he chose, but it is a sad life at best.