Eamon De Valera and Winston Churchill were never friends. Famously de Valera had brilliantly defended Ireland's neutrality during World War II following a verbal broadside from Churchill. One can imagine that matters between the two leaders were cool to freezing.
According to Dennis Kelly, a former literary assistant to Churchill, the British prime minister liked to tell the following amusing story: 'British bomber over Berlin, caught in searchlight, flak coming up, one engine on fire, rear-gunner wounded, Irish pilot mutters: Thank God Dev kept us out of the bloody war.'
Dev and Churchill met face to face once at lunch in Downing Street in 1953. It all passed off amicably. Afterwards Churchill told the story that when he said to the Irish Prime Minister that, in his view, the situation in the United Kingdom was serious but not hopeless; the Irish Prime Minister replied that the situation in his country was hopeless but not serious.