Unlike his mother-in-law who had supported the Parliamentary cause, Winston had the misfortune of fighting on the losing side of the war – for which he, like so many other Cavaliers, was forced to compound; in his case £446 18s.
I modsætning til sin svigermor, som havde støttet Rundhovederne – dvs. parlamentet – havde Winston haft det uheld at kæmpe på den tabende side i krigen, hvorfor han, som så mange andre kavalerer, blev tvunget til at betale erstatning – i hans tilfælde £446 18s.