March 24, 2025

[Of Winston Churchill] He is a terrible burden for any Govt. to carry—someone said of [his father] Randolph Churchill that he was the kind of man who would like to be the bride at a wedding and the corpse at a funeral—the same applies to his more brilliant son.

Cuthbert Morley Headlam (1876-1964), British Conservative politician, Diary, 20 July 1927, Jay p.172

Do you find this picture of Churchill hard to reconcile with the generally good reputation he continues to enjoy in the face of revisionist historians? Do you think he deserves the sobriquet “the greatest man of the twentieth century”?

The date of Headlam’s diary entry—1927—is all important. For all but two years between 1908 and 1929, Churchill was a cabinet minister, but between 1929 and 1939, he was a lowly backbencher, all while his party—the Conservatives—formed the government. Those ten years “in the wilderness” bespeak the distrust of him by many, especially in his own party. After all, he switched parties twice, “ratting” to the Liberals in 1904 and “re-ratting” back in 1924.