He called them "Monumental and very Powerful Bases [that] have become part of a Great American Heritage," even though the Pentagon had said it was open to discussing the move.
Politically risky as it is, Trump has a history of his own in repeatedly defending the symbols of a time many consider deeply offensive, even more so now amid a nationwide reckoning over race.
Keeping alive the legacy of the Confederacy -- from statues glorifying its military heroes to the brandishing of its rebel flag -- to millions of Americans is a painful reminder of what it stood for: the nation's racist foundation.
Others, however, like the president, and some of his backers, insist the memorials are part of the nation's history not to be banished -- despite the men and ideas implicitly being honored.
In Trump's first news conference as a presidential candidate, asked whether he agreed with then-South Carolina GOP Gov. Nikki Haley's decision to remove the Confederate battle flag from the State Capitol grounds, Trump said yes.
"I think it probably does, and I think they should put it in the museum," he answered in June 2015. "Let it go. Respect whatever it is you have to respect because it was a point in time, and put it in a museum. But I would take it down, yes."
But since winning the White House, Trump's rhetoric has taken a turn.
Trump's argument this week against renaming the bases mirrors language he used another time racial tensions brewed during his presidency.
Following the "Unite the Right" rally on Aug. 11 and 12, 2017, in Charlottesville, where white nationalists protested the city's decision to remove a statue of Robert E. Lee, and one counter-protester was run over and killed, President Trump declared there were "very fine people on both sides" while defending the protesters and arguing for keeping the statue.
"This week, it is Robert E. Lee. I noticed that Stonewall Jackson is coming down," he said from the lobby of Trump Tower. "I wonder, is it George Washington next week? And is it Thomas Jefferson the week after? You know, you really do have to ask yourself, where does it stop?"
Two days later, he doubled down on the notion in a Twitter thread reading: "Sad to see the history and culture of our great country being ripped apart with the removal of our beautiful statues and monuments...the beauty that is being taken out of our cities, towns and parks will be greatly missed and never able to be comparably replaced!"
After former Vice President Joe Biden released a campaign launch ad last April with a clip from the now infamous Charlottesville news conference, Trump continued to defend the leader of the Confederate Army who notably fought against the Union and for states' rights to maintain slavery.
"Whether you like it or not, he was one of the great generals. I have spoken to many generals here, right at the White House, and many people thought of the generals, they think maybe he was their favorite general. People were there protesting the taking down of the monument of Robert E. Lee. Everybody knows that," Trump told reporters on the White House South Lawn.
When asked about his "fine people on both sides" comment, Trump maintained he "answered perfectly."
The president, as is his pattern, isn't budging, even as politicians on both sides of the aisle voice support for moving Confederate statues and flags to museums, to preserve the history but not to seem to promote it in an insensitive way.
Even Sen. Mike Rounds, a South Dakota Republican and member of the GOP-controlled Senate Armed Services Committee, which approved a measure to rename U.S. military assets named for Confederate officers, asked directly Thursday about the president's opposition, said, "Well, we'll work that through, but we're moving in the right direction."
"I agree with the president that we don't want to forget our history. We don't want to forget what's happened in the past, but at the same time that doesn't mean that we should continue with those bases with the names of individuals who fought against our country," he said.
House Speaker Nancy Pelosi on Wednesday called for the removal of 11 Confederate statues from the Capitol, writing in a letter to the leadership of the Joint Committee on the Library, "Their statues pay homage to hate, not heritage."
Trump, she said Thursday, "seems to be the only person left who doesn't get it."
As some lawmakers respond to protesters targeting Confederate monuments following George Floyd's death, the president and his aides are sticking with a strategy that helped him win in 2016.
Former Trump campaign surrogate and now White House press secretary Kayleigh McEnany said in a White House briefing Wednesday, following Trump's Twitter thread, that the possibility of renaming the military bases was "an absolute non-starter" for the president and he "fervently" opposes it, arguing it's disrespectful to American soldiers killed overseas.
"Where do you draw the line? Should George Washington and Thomas Jefferson and James Madison be erased from history? What about FDR and his internment camps? Should he be erased from history? Or Lyndon Johnson, who has a history of documented racist statements," she said.
In 2017, John Fabian Witt, a professor of history at Yale, predicted in the New York Times after Trump's Charlottesville remarks that the debate over Confederate monuments would continue rising to the surface.
"The amazing thing is that the president is doing more to endanger historical monuments than most of the protesters," he said. "The alt-right is producing a world where there is more pressure to remove monuments, rather than less."
While Trump and the White House argue for preserving the South's heritage and culture, a growing number of corporations, schools and sporting leagues have attempted to reconcile the role racism has played in their own histories.
Roughly two hours after Trump's thread on the "history of Winning, Victory, and Freedom" that he argued came with the Confederate South, NASCAR made a ground-breaking statement that it was banning the Confederate flag at all of its races.
"The display of the confederate flag will be prohibited from all NASCAR events and properties," the statement read, notably using a lower case "c."
The change came after NASCAR's only full-time black driver Bubba Wallace said one day before: "No one should feel uncomfortable when they come to a NASCAR race. It starts with Confederate flags. Get them out of here. They have no place for them."
It was just back in February that the president had Air Force One fly over the stands of the Daytona 500 as he made his first visit as president to a NASCAR race.
The symbol of Southern secession has become a common sight at those races -- and at the president's rallies, which Trump is slated to return to next week.
In the wake of the national outrage over race and policing, it remains to be seen if the Confederate flag will be on display less -- or more so.