What progressives get wrong about Winston Churchill

Please be advised that the following article contains outdated racial representations and views some readers may find distressing. Only joking! Yet that always seems to be the unspoken line running through modern academia’s head whenever the subject of Winston Churchill is raised.

This year sees the 150th anniversary of Churchill’s birth; it will also see cohorts of academics jostling to tell us just how horrifically racist, imperialist, sexist and probably transphobic he was. As though that could be a surprise. Yet what might genuinely surprise many now is to learn that in certain respects, Churchill was in the vanguard of the woke movement. He was a progressive pioneer.

Churchill was very at ease in the company of gay men at a time when homosexual acts were illegal

And yes, that goes for his trans credentials too. In 1920, during the course of a midnight champagne-fuelled conversation with his sculptor cousin Clare Sheridan, Churchill declared: ‘In my next incarnation, I intend to be a woman.’ He went on to elaborate: ‘I mean to be an artist, I shall be free and I shall have children.’ He was at that moment wearing a (non-binary) silk Jaeger dressing gown. (In matters of clothing, he was always in touch with his metrosexual side: the codebreaker Sarah Baring recalled seeing Churchill moving through the Admiralty in the small hours swathed in a vast, shimmering, richly patterned oriental dressing gown.)

Churchill was also ahead of the game on today’s vexed ‘work/life balance’ argument. Talking to his doctor in the early 1950s, he averred that any satisfactory resolution of the Cold War might happily lead to huge rises in global production, which in turn would mean ‘people could have what they needed more than anything else – leisure… They could work hard for four days and have the other three to enjoy themselves.