You've successfully subscribed to American Purpose
Great! Next, complete checkout for full access to American Purpose
Welcome back! You've successfully signed in.
Success! Your account is fully activated, you now have access to all content.
Success! Your newsletter subscriptions is updated.
Newsletter subscriptions update failed.
Success! Your billing info is updated.
Billing info update failed.

The Art of Losing

Advice for an outgoing President.

Lee Pollock

In the early morning hours of July 26, 1945, Winston Churchill awoke with a start. As he later recounted, he felt a “sharp stab of almost physical pain. A hitherto subconscious conviction that we were beaten broke forth and dominated my mind.”

The source of his anxiety was the first British general election in ten years. Balloting had taken place three weeks earlier, but the announcement of the result was delayed for the votes of military personnel overseas. There had been straws in the wind—several by-election defeats for the Tories and a gap in rudimentary opinion polls—but the outcome was shocking. The opposition Labour Party had expected a Tory majority of at least thirty; but by lunchtime, the socialists were ahead by almost two hundred seats and over four million votes.

Despite his foreboding, Churchill—and the world—was stunned, with Americans unable to fathom how Britain’s wartime leader could be so unceremoniously ejected. Churchill submitted his resignation to the King that very evening and quickly moved out of No. 10 Downing Street, literally with no place to go. (The Churchills ended up borrowing the London flat of their daughter and son-in-law.) When his wife Clementine suggested the result might be a blessing in disguise, Churchill retorted, “At the moment, it seems quite effectively disguised.”

But Churchill’s natural magnanimity came to the fore, his statement that evening noting, “The decision of the British people has been recorded. Immense responsibilities fall upon the new government, and we must all hope they will be successful in bearing them.” In private, when his physician complained about the ingratitude of the British people, Churchill replied, “I wouldn’t call it that. They have had a very hard time.” To another associate, he added, “They are perfectly entitled to vote as they please. This is what we’ve been fighting for.”

It is a mark of America’s continuing fascination with Churchill that the presidency of Donald Trump has been marked by repeated Churchill allusions, from Trump’s reclaiming a bust of Churchill for the Oval Office to Kayleigh McEnany’s likening the President’s June walk across Lafayette Square to Churchill’s tours of a devastated London during the Blitz. (Not everyone appreciates the analogies. A descendant of Churchill’s titled a recent op-ed, “Trump compared himself to my grandfather—but he’s no Winston Churchill.”)

With no concession yet from President Trump, we don’t know whether he’ll model the magnanimity that Churchill displayed in both victory and defeat. If the President is looking to his place in history, he’ll be well advised to do so.


Churchill was considerably weakened by the strain of war, and many Conservatives hoped he would turn the party over to Anthony Eden; but Churchill hung on relentlessly. In October of 1951, just a month before his seventy-seventh birthday, he returned to power, albeit with a miniscule majority. He finally retired four years later. He was in his eighty-first year.

Will Donald Trump be too restless for the life of an ex-president? Unlike Churchill, who reveled in painting, read and wrote voraciously, and maintained a wide circle of confidants, President Trump is said to have a limited circle of close friends and few hobbies other than golf. (Churchill gave up on golf early. It was said that he “foozled” his drives.) So, the attraction of remaining “in the arena,” in Teddy Roosevelt’s words, might be irresistible. There is already talk of a Trump presidential candidacy in 2024. He likely knows that Grover Cleveland won the presidency in 1892 by defeating the Republican who had beaten him four years earlier.

By the time Churchill returned to power, Britain had tired of five years of real socialism (not the limp version half-heartedly spouted by today’s progressive Democrats); but the new government did little to reverse it. The country remained divided. A year later Churchill asserted, “Four-fifths of both parties agree on four-fifths of what should be done; and we all sink or swim together on our perilous voyage into the unknown.”

Can an ideologically divided America, especially with a split Congress, find four-fifths of anything on which to agree? Churchill—who famously, if perhaps apocryphally, said Americans would always do the right thing after trying everything else—would be interested to know.

Lee Pollock, former executive director of The International Churchill Society, is a Florida-based writer and speaker on Winston Churchill.