Winston Churchill and Donald Trump: The Elite’s Favorite Villains
Racist, bigot, reckless adventurer, warmonger, unreliable, autocratic, imperial, self-promoter, dangerous. These terms of derision and disdain may sound familiar to Americans who imbibe legacy media and elite portrayals of President Donald Trump. Yet those same terms were frequently used to describe another political figure during the 1920s and 1930s. That political figure was Great Britain’s Winston Churchill, who, like Trump today, suffered the slings and arrows of elite critics who did everything they possibly could to keep Churchill out of power.
Perhaps, then, there is a deeper reason why President Trump upon taking office in 2017 and again in 2025, returned the bust of Winston Churchill to the oval office.
The political elites in the United States who deride Trump have one thing in common — whether they are Democrats or Republicans, of the left or of the right — an instinctive disdain for the president, primarily because he isn’t one of them, but also because he doesn’t play by their political and social rules. That elite disdain manifests itself in Democratic Party talking points; the Bush-McConnell wing of the Republican Party’s opposition to anything Trump does; George Will columns; MS Now’s daily fare of Trump Derangement Syndrome; virtually every New York Times and Washington Post political story, editorial, and op-ed piece; most ABC, NBC, CBS, CNN, and PBS “news” programs; and increasingly by opposition to Trump’s policies by members of the federal judiciary.
Churchill faced that same elite disdain throughout his political career. Although Churchill was a member of the British political elite, he didn’t play by the expected elite political rules. He changed political parties twice. He opposed his own political party’s social policies, how to wage war, Bolshevism, India, King Edward’s marriage, appeasement, and other matters. He was often ridiculed by his political colleagues. Leo Amery compared Churchill’s racial views to Hitler’s. Others called him an “English Mussolini.”
When Churchill wrote the first volume of his history of World War I, one colleague remarked, “Winston has written an enormous book all about himself and calls it ‘The World Crisis.’” Lord Balfour referred to it as, “Winston’s autobiography disguised as the history of the universe.” Conservative colleague Samuel Hoare called Churchill “offensive” and “mischievous.” Prime Minister Stanley Baldwin commented that for all of Churchill’s gifts, he lacked “judgement and wisdom.” Rab Butler called Churchill a “drunken adventurer.” Labor M.P. Aneurin Bevan during World War II called Churchill a “fascist” and accused him of promoting policies that make “the poor carry the rich on their backs.” Journalist Leopold Maxse described Churchill as “half-alien and wholly undesirable.”
Even after Churchill had been proved right again and again about Hitler’s threat to Britain and the world, the elite British establishment wanted Lord Halifax, not Churchill, to replace Neville Chamberlain as Prime Minister in May 1940. Jock Coleville, who served as Churchill’s private secretary, later noted that Churchill was “viewed with grave misgivings” by the British establishment, everybody was “frightened of Churchill, they thought he was an adventurer who might do the most extraordinary things and undertake the most astonishing adventures.” Joe Biden, like Halifax, was a member in good standing of the elite political establishment in America and therefore preferable in their minds to Trump even when Biden had difficulty delivering an intelligible complete sentence.
Churchill as Home Secretary used the military to quell workers’ strikes, and was criticized for doing so. Trump has been criticized for sending military forces to protect federal buildings that were under siege by rioters. Churchill, like Trump, also came under attack for the language he used. Churchill called Mahatma Gandhi a “fakir” and a “malignant subversive fanatic.” He called the people of India a “beastly people” with a “beastly religion.” And Churchill, like Trump, was criticized for equating socialism with totalitarianism. Like Trump, Churchill’s DNA was resistant to political correctness.
Trump, like Churchill, experienced years in the political wilderness when he was ravaged by lawsuits and politically-inspired prosecutions. Perhaps, then, there is a deeper reason why President Trump upon taking office in 2017 and again in 2025, returned the bust of Winston Churchill to the oval office (Presidents Obama and Biden had removed it). In his majestic biography of Churchill, Martin Gilbert wrote words about Churchill during his years in the political wilderness that could also apply to Trump during the four years he, too, was in the political wilderness: “Isolated from all his former Cabinet colleagues, rejected by a definite majority within the Conservative Party, only the strength of [his] convictions drove him forward, and sustained him, in his much derided course.”
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