Roughly 48 hours before his positive test, Trump was on a debate stage, mocking Democratic rival Joe Biden for being vigilant about facial coverings.
"I don't wear a mask like him," Trump said. "Every time you see him, he's got a mask. He could be speaking 200 feet away, and he shows up with the biggest mask I've ever seen."
"That, right there, was a masculinity contest," said Valerie Sperling, a political scientist at Clark University who has authored several books related to gender. "Trump was ridiculing Biden, basically saying that Biden is weak and fearful, compared to himself."
It's now been a week since President Trump revealed on Twitter that he tested positive for the coronavirus. All the while, he has sought to project toughness and strength in the face of his diagnosis, but details about his condition have sometimes been hard to come by.
Presidents, including Massachusetts native John F. Kennedy, have historically been reluctant to show any weakness when facing health scares, in part because they have often presented themselves as beacons of masculine vigor.
Sperling notes Trump has tried hard over the years to cultivate a reputation for physical prowess. This is a president who once assured voters, in a different debate, that there is "no problem" with the size of his male anatomy.
And the doctor who wrote a letter vouching for Trump's health in the last election later said the candidate told him to say things, like, "his ... strength and stamina are extraordinary."
"Trump's supporters are really invested in his appearance of masculinity, and this was true after the diagnosis, too," Sperling said.
The president was quickly hospitalized after being diagnosed with COVID-19. But he claimed in a social media video that his transfer to Walter Reed National Military Medical Center was not a bad sign but rather a take-charge move that would keep him "out front."
It was unclear how staying in a hospital for four days would keep the president more engaged than he would have been in the White House.
It also was unclear, when Trump was admitted to Walter Reed, how severely COVID-19 was hampering his breathing. At a news conference the next morning, the president's physician, Dr. Sean Conley, dodged questions about whether Trump had required supplemental oxygen.
"He's not on oxygen right now," Conley told the press.
A reporter, seeking clarification, asked whether Trump had received any oxygen at all.
"He's not needed any this morning, today, at all," Conley responded.
To historian David Woolner, the evasiveness of Trump's doctor recalled the kinds of statements President Franklin Roosevelt's doctor used to issue when health questions came up, as they did in the 1944 campaign.
"His physician, the surgeon general, Dr. [Ross] McIntire, said Roosevelt was in fine health for a 'man of his age,' which was a less than complete answer," Woolner said.
Roosevelt was 62 at the time and suffering from congestive heart failure, as Woolner chronicles in his book, "The Last 100 Days: FDR at War and at Peace."
The doctor's evaluation was arguably true, in the strictest sense, since Roosevelt already had surpassed the life expectancy of someone born when he was. But it further obscured the medical status of a president who had spent his career concealing mobility limitations caused by polio.
Other presidents also have worked to keep the extent of their ailments out of public view, in part because they had images to maintain.
"President Kennedy had some serious health issues and very difficult trouble with his back and lots of pain medications," said Woolner, a senior fellow at the Roosevelt Institute and professor at Marist College. "And, of course, as we know, President Reagan started to suffer from early forms of dementia later on in his presidency."
Reagan was diagnosed with Alzheimer's disease several years after leaving office.
These were men with money, power, movie-star looks and charm to match. Medical problems didn't fit the picture.
"Part of a particular masculine identity is that you're tough, that you don't get sick," said Tom Nichols, a national security professor at the U.S. Naval War College in Newport, Rhode Island, who has written about masculinity and the presidency.
Nichols said concerns about a president's health can be overblown; it is a desk job, after all. And sharing too much information could make the United States appear vulnerable to adversaries.
"But when the entire country is suffering from a pandemic, and over 200,000 people are dead, and then the president contracts this disease, people of course want to know what's going on," he added, "especially because they're 30 days away from having to choose another president."
This segment aired on October 9, 2020.