He has especially mocked wearing masks, continuing to do so despite promising he would -- and against the advice of public health officials that everyone should wear them to save thousands of lives.
Just this week, on a national debate stage with 73 million viewers tuned in, he attacked Democratic nominee Joe Biden for wearing one.
"I don't wear masks like him. Every time you see him, he's got a mask. He could be speaking 200 feet away from it, and he shows up with the biggest mask I've seen," Trump said, bragging about the large crowds of supporters at his outdoor rallies, many not wearing masks.
As far back on April 3, when the Centers for Disease Control and Prevention first recommended Americans wear face coverings in public, changing earlier guidance that it wasn't necessary, it was Trump who made the announcement at a task force briefing -- but he stressed the practice was "voluntary" and that "you do not have to do it."
Ever since, Trump has resisted wearing one.
"I just don't want to be doing -- somehow sitting in the Oval Office, behind that beautiful, Resolute Desk, the great Resolute Desk, I think wearing a face mask -- as I greet presidents, prime ministers, dictators, kings, queens, I don't know, it somehow, I don't see it for myself," Trump said.
It took him more than two months to don one in public, following the CDC's recommendation, when he visited wounded service members at the Walter Reed National Military Medical Center in Maryland.
"When you are in a hospital, especially in that particular setting when you are talking to a lot of soldiers, people that in some cases just got off the operating table, I think it's a great thing to wear a mask," Trump said in July, calling it "patriotic."
Trump faced questions about risks to his own health as the pandemic spread across America, but maintained a lack of concern that he could contract the virus.
Asked in an interview with Maria Bartiromo on Fox Business in May about the possibility that House Speaker Nancy Pelosi could assume the presidency if Trump and Vice President Mike Pence were to fall ill, the president scoffed at the idea.
"We'll keep our vice president very healthy and I'll stay healthy," he said. "Never going to happen."
In August, talking about masks, he said, "Maybe they’re great, and maybe they’re just good. Maybe they’re not so good.”
In a White House briefing just last month, Trump was asked why he doesn't wear a mask to set an example, instead of encouraging supporters who view rules requiring masks as a violation of personal freedom.
Once again, he mocked Biden.
"Well, I'm tested, and I'm sometimes surprised when I see somebody sitting and -- like, with Joe. Joe feels very safe in a mask. I don't know, maybe he doesn't want to expose his face," Trump said on Sept. 16. "There's no reason for him to have masks on."
"We get tested -- I'm tested. I have people tested. When people come into the Oval Office, it's like a big deal. No matter who they are -- if they're heads of countries, they all get tested. So I'm in sort of a different position. And maybe if I wasn't in that position, I'd be wearing it more," he continued.
ABC News Contributor John Cohen said it's essential in a public health crisis to set an example.
"The president, by his own admission, downplayed the severity of the pandemic. From the start he sent mixed messages on the wearing of masks and other protective measures recommended by his own public health experts," said Cohen, a former acting undersecretary for intelligence at the Department of Homeland Security. "He, his staff and his campaign ignored CDC guidance and that high-risk behavior not only confused Americans -- placing our communities at greater risk -- but it also made the White House a more dangerous place to work and visit."
In September, a frustrated Trump asked a White House reporter to remove as mask while asking a question: "If you don't take it off, you're very muffled."
Despite the president and his close adviser Hope Hicks getting sick, a White House spokesman said Friday afternoon that mask wearing still will not be required at the White House, where many had gone without them for months.
It will instead remain a personal choice, the spokesman said.
But as staffers gathered on the South Lawn to watch their boss leave for Walter Reed Friday afternoon, most, if not all, were wearing masks.
And so was the president, one with a presidential seal.