President Trump at times told staff wearing masks in meetings to “get that thing off,” an administration official said. Everyone knew that Mr. Trump viewed masks as a sign of weakness, officials said, and that his message was clear. “You were looked down upon when you would walk by with a mask,” said Olivia Troye, a top aide on the coronavirus task force who resigned in August and has endorsed former Vice President Joseph R. Biden Jr…

[This week’s] was also a byproduct, former aides said, of the recklessness and top-down culture of fear that Mr. Trump created at the White House and throughout his administration. If you wanted to make the boss happy, they said, you left the mask at home…

Aides were divided on the risks. Jared Kushner, Mr. Trump’s son-in-law and senior adviser, and Dan Scavino, the White House social media director, were among the least concerned, colleagues said. They viewed themselves as protected because of the testing available to them and maintained that getting the virus was not a death sentence…

Colleagues said that newcomers to Mr. Trump’s orbit, like Kayleigh McEnany, the White House press secretary, never wore a mask in his presence, in what was interpreted by other staff members as an attempt to please the new boss.