I rather doubt he was gay. He probably had some same-sex encounters early in his life, which wasn't uncommon for a gentleman of his social class in that era. He was friends with a number of gay men throughout his life but I don't think he had dalliances with any of them. read more
As a rule, Sir Winston Churchill disliked women. While he seems to have felt relaxed in the company of homosexuals and regarded their (illegal) activities as a subject for good-natured ribaldry. read more
Sir Winston Churchill used to rate women at parties out of 1,000, wrote to his mother-in-law that sex with her daughter was “delightful” and was definitely not gay, a historian has said. read more