I wasn't his biggest fan, but PJ O'Rourke could be amusing in his contrarianism, and I had wondered what he thought of Trump, as I hadn't noticed him writing much in recent years.
So, Googling it up now, I am pleased to see that he had anti-Trump and anti-Brexit views, meaning he was more sensible than most conservative/libertarians in his own country (and those in Australia, like Tim Blair). From an article in New Statesman in 2020:
O’Rourke sprang back into the national spotlight during the 2016 presidential election by announcing that he was going to vote for Hillary Clinton, not Donald Trump.
He puts the decision down to his natural conservatism. “Politics is a matter of least worst,” he told me when I recently stayed at his farm. “She was the devil I knew – she was going to be another eight years of Obama, which we had endured. Donald Trump? I knew people who knew him. Nobody liked him. I just thought he was unstable…dangerous. I still do.”...
he hasn’t changed his mind about Trump. “In fairness, his administration has not been as bad as I thought it might be,” he reflected. “But there have been moments when one has gone: ‘Whoah!’” What he described as Trump’s “group hug” with the North Koreans, and “stirring things up with Iran” are just two examples.
O’Rourke believes that the Founding Fathers made the presidency too powerful by giving it control of foreign policy – something he recently discovered Benjamin Franklin had opposed. “He thought it should have been a committee,” he said.
“Trump certainly is not a conservative in the sense of conserving the status quo. Arguably Clinton was more so. He is a radical, a populist one, and I don’t like populism anyway. Populism is, like, ‘The government should give me things I like or get rid of the things I don’t like’… The Nazis were populist, Mussolini was populist.”
For similar reasons, the perennial sceptic says he would have taken the Remain side in the 2016 referendum on EU membership. “I would have been against Brexit strictly on practical grounds – Britain and Europe had become too thoroughly integrated to do something as radical as Brexit.”
Though sympathetic to the Leave cause over European meddling, and happy to give Europe “a kick up the pants”, it was his conservatism that said “stay”.