Sir Winston Churchill

Churchill would arrive at your dinner slightly late, already warm on the first drink of the day, which he’d had at 11 AM in his bath. He drank in a specific sequence — champagne before lunch, whisky and water through the afternoon, champagne again at dinner, port after — and he did not believe, contra his doctors, that any of it was a problem. He wrote four million published words in his lifetime. He painted 500 canvases. He ran a war. Most of it was done with a cigar in his left hand and a glass in his right, and he lived to 90, and he’d tell you this was a matter of stamina, which he considered the most underrated virtue in a civilized man.

He’d order for the table. Beef. He’d always order beef. If the menu didn’t have it, he would, very politely, ask the kitchen to find some. He traveled, when he could, with his own cook, his own valet, and his own crate of champagne. Pol Roger. Vintage. Pre-1928, if the cellar allowed. He became friends with Odette Pol-Roger after the war and wrote her letters about the specific gravity of her family’s wines with the precision of a man who’d thought about them longer than most people think about any one thing.

The first hour of dinner, he’d mostly listen. This is not the Churchill of the newsreels. He listened. He watched. He assessed. Clementine Churchill, married to him for 57 years, said in a rare interview that her husband’s apparent bombast was “90 percent armour” — that in private he was often quiet, often depressed (“I call it my Black Dog”), and that he saved his talking for the occasions when he had something precisely calibrated to say. By the second hour, he’d have decided what kind of evening it was. If the company was sharp, he’d join the fight. If somebody at the table was a fool, he’d turn the full battery on them — not cruelly, but thoroughly, with the understanding that the fool was doing the company a disservice by occupying a seat that could have gone to someone better. Lady Astor once told him at a dinner: “Winston, if I were your wife, I’d put poison in your coffee.” He replied: “Madam, if I were your husband, I’d drink it.” Everyone tells this story. What people leave out is that Lady Astor laughed hardest. She loved him. The line was the affection.

By the third hour, he’d be telling you about a specific cabinet meeting in 1940 — the one on May 28, when Lord Halifax proposed negotiating with Hitler through Mussolini and Churchill talked five men out of it over the course of a single afternoon. He’d walk you through the argument in detail, because it was the argument he was proudest of winning. “If this long island story of ours is to end at last, let it end only when each one of us lies choking in his own blood upon the ground.” He wrote it first as a memo. Delivered it in person. Won the vote. He’d still, thirty years later, remember exactly where everyone had been sitting in the room.

What you’d remember the next day: not the line about the poison. Not the cigar smoke. The moment, somewhere around midnight, when he looked at you over the rim of his glass and said — quietly, without performance — “I am perfectly prepared to go to meet my Maker. Whether He is prepared for the ordeal of meeting me is another matter.” And then he’d laugh, huge laugh, genuine, and ask for another port, because there was still a lot of evening left.

Three questions to start with:

• May 28, 1940. The cabinet meeting with Halifax. Walk me through the argument you won.
• The Black Dog. Clementine said you were depressed more often than the public ever knew. What got you through the worst week of it?
• You wrote six million words, painted 500 canvases, won two Nobel-worthy achievements (one was), saved the West, and drank more than any of your doctors recommended. What’s left on the list?