Churchill’s association with horse racing as an owner and breeder in his later years is detailed in an interesting article in the Thoroughbred Racing Commentary. The 2,000 word piece by Sean Magee describes how Churchill, with the encouragement of his son-in-law Christopher Soames, bought his first race horse in 1949 when he was already 74 years old. Churchill owned several horses over the next years, including Cybarine, High Hat, Vienna, and Le Pretendant. The most successful horse he had, however, was Colonist II, the first horse he had bought. As the article indicates, while Churchill entirely enjoyed owning a racing stable the endeavor always puzzled his wife Clementine. In 1950 she wrote that “I do think this is a queer new facet in Winston’s variegated life. Before he bought the horse (I can’t think why) he had hardly been on a racecourse in his life. I must say I don’t find it madly amusing.” The article is available here.