This chapter examines Winston Churchill’s attitude to so-called policies of ‘appeasement’ in his political career after he became prime minister in 1940. Whilst Churchill helped to damn Chamberlain’s appeasement through his speeches and writings, he did not wish to eliminate it as a policy option for all time. Despite this, and largely through his own rhetoric, Churchill effectively limited his room for manoeuvre in his later political career, especially when he was, once again, prime minister between 1951 and 1955. In continuing in the pragmatic tradition of British foreign policy, Churchill sought to cast policies of conciliation in a manner designed to demonstrate that appeasement’s ‘illegitimacy’ as a strategy was not a given but contingent on circumstances. However, the failure to successfully demarcate détente and appeasement caused Churchill serious political difficulties, especially as initiatives such as his 1953 ‘Eastern Locarno’ proposals were widely attacked as being a reversion to the discredited policies of the 1930s.