From Confederate statues to airports named after a movie star who once said he believed in white supremacy, the president denounced steps that would strip racists of their monuments and memorials, rather than the ones they would keep honors intact.
And he promoted a video of a white couple brandishing weapons as peaceful black protesters marched past their ornate mansion, images that underscored an ongoing racial divide.
Attendees and those around him have denounced everything from the removal of "Gone with the Wind," one of Trump's favorite movies, to the name change of Aunt Jemima's pancake syrup, discounting the stereotypes that they have long been called racists.
Beyond simply voicing opposition to the changes, Trump has aggressively sought the prosecution of people who have defaced or destroyed statues in American cities. This week, he tweeted that the FBI wanted posters seeking information about people who disfigured a statue of Andrew Jackson near the White House. He wrote Tuesday morning that he was "tracking" vandals who dumped red paint on "magnificent" George Washington statues in Manhattan and encouraged them to turn themselves in to police.
"Give yourselves up now!" Trump wrote.
On Friday, he signed an executive order behind closed doors that threatens to withhold federal funds from local governments that cannot protect the monuments in his jurisdiction. It is not legally clear whether that threat can be acted upon, and many saw the executive order as a political theater meant to exploit an emerging cultural divide.
However, Trump has continued to oppose any attempt at a name change or removal, even when those who were removed took openly intolerant or racist views.
"Can anyone believe Princeton just left the Woodrow Wilson name for his respected policy center?" Trump tweeted after the university announced that it would remove the 28th president from its school of public policy and a residential university.
The Princeton president had said in a statement that the school's board of trustees "concluded that Woodrow Wilson's racist thinking and policies make him an inappropriate namesake for a school or university whose academics, students, and alumni must be firmly against racism in all its forms. "
As President of the United States, Wilson once called racial segregation "a benefit" and said that slaves "were happy and well cared for." As Princeton's president, he denied admission to African-American men and tried to exclude them from the history of the school. The decision to remove her name was hailed by former First Lady Michelle Obama, who graduated from Princeton in 1985.
As president, Trump has not quoted Wilson extensively and has shown a greater affinity for other presidents, such as Jackson, a slave owner whose portrait is hanging in the Oval Office. Still, Trump's shock that Wilson's name would be removed followed his pattern of opposing any attempt to rebrand or remove historical markers.
In the same tweet, Trump criticized efforts to rename an airport in Orange County, California.
"Now Democrats Do Nothing want to remove John Wayne's name from an airport," he wrote. "Unbelievable stupidity!"
Democrats in Orange County are pushing to rename the airport, citing the western film star's professed support for white supremacy in a 1971 Playboy interview, in which he derogatoryly viewed derogatory views of African-Americans, natives Americans and movies with gay characters.
"While some outside Orange County may not be aware of John Wayne's beliefs in white supremacy, many Orange County residents have been calling for his removal for years," said county party president Ada Briceño in a release. "We are seeing renewed calls for this now, and it is time to change."
In an interview last year, the actor's son Ethan Wayne said his father's words in Playboy's questions and answers were being taken out of context and that his father "took everyone to the letter."
Trump has long embraced John Wayne's arrogant personality as a conservative archetype worth modeling, be it his exaggerated masculinity or his "law and order" mantra that often ignores due process. Trump visited Wayne's birthplace in Iowa during his 2016 presidential bid, where he stood in front of a wax statue of the actor and declared himself a "long time" fan.
"We love John Wayne," he said when the actor's daughter Aissa declared that if her father were alive, she would endorse Trump.
"We need someone like Mr. Trump with leadership qualities, someone with courage, someone who is strong like John Wayne," he said.
As president, Trump has consistently opposed the removal of Confederate statues and monuments, though he said during a Fox News event last week that he would support putting some statues in museums.
Earlier this month, McEnany demonstrated a much greater passion by discussing the temporary removal of "Gone With the Wind" from HBO Max's streaming library, a decision he made as the start of a slippery slope.
"They told me that you can no longer find on HBO & # 39; Gone with the Wind & # 39; because somehow that is now offensive," he said. "Where do you draw the line?"
The film was then restored to streaming service with a new introductory disclaimer (HBO and CNN share a parent company, Warner Media).
A person familiar with the matter said Trump himself also privately criticized the removal of "Gone with the Wind," a film that fueled racist stereotypes while overlooking the horrors of slavery, but which has hailed it as one of the largest ever made.
Trump cited the film when complaining about this year's Oscar winner for best picture, the "Parasite," made in South Korea, during a campaign rally earlier this year.
"Can we get Gone with the Wind back, please?" he asked after the award ceremony in February.