Churchill's actress daughter Sarah was married for a time to the music-hall entertainer Vic Oliver. Churchill did not particularly like him. Out walking one day, Oliver asked his father-in-law whom he had admired in the war.
"Mussolini," said Churchill. "He had the courage to have his son-in-law shot." In 1944, after his fall from power and subsequent rescue by German commandos, Mussolini had his son-in-law shot for treason.
* * *
Once when Churchill was visiting the White House, President Roosevelt wheeled himself along to the British premier's bedroom and, opening the door unexpectedly, found Churchill stark naked. Unembarrassed, Churchill said, "You see, Mr President, we British have nothing to hide."
邱吉爾的女兒莎拉是演員，曾與雜耍劇院娛賓演員維克．奧立佛為夫婦。邱吉爾不怎麼喜歡這個女婿。有一天，奧立佛和岳父同行，問他戰時最欣賞的是誰。
邱吉爾說：「是墨索里尼。他有勇氣槍斃女婿。」一九四四年，墨索里尼倒臺並獲德國突擊隊救出之後，以叛國罪名，把女婿槍斃。
* * *
有一次，英國首相邱吉爾在白宮作客，羅斯福總統推着輪椅，走到他卧房前，出其不意，打開房門，看見邱吉爾一絲不掛。邱吉爾不慌不忙，說道：「總統先生，你看，我們英國人是坦蕩蕩的。」