President Trump posted the photograph intending to belittle Nancy Pelosi.
“Nervous Nancy’s unhinged meltdown!” he wrote on social media in 2019, captioning a picture taken by a White House photographer of Ms. Pelosi, then the House speaker, her bright blue suit popping as she stood at a long oval table of graying white men in dark suits, all seated, pointing her finger straight at Mr. Trump.
Instead, the photograph became an instant classic as it spread across the internet, an iconic image of the most powerful woman in Washington, unafraid and unbowed as she stood up to an erratic and inexperienced president who did not like to be challenged.
Ms. Pelosi’s fans celebrated it, and she quickly made it her header image on Twitter.
It would come to encapsulate a crucial piece of Ms. Pelosi’s legacy — the first and only woman to serve as speaker and the rare woman in Washington who challenged the president effectively and directly to his face, unmoved by his bullying tactics and unwilling to give him the upper hand.
“Everyone sort of cowers in his presence, and she would not,” said Debbie Walsh, the director of the Center for American Women and Politics at Rutgers University. “She was absolutely sure of herself and he is not at ease with strong, powerful women. He always looked like she got him kind of back on his heels.”
Ever since the president arrived in Washington, Ms. Pelosi, who would go on to preside over two impeachments that failed to remove Mr. Trump, has confounded him. He has tried to intimidate, undermine and embarrass her. But those efforts more often than not backfired.
In the scene pictured, Ms. Pelosi had been pressing Mr. Trump on his decision to pull troops out of Syria.
“I had concerns that all roads seemed to lead to Putin,” Ms. Pelosi told reporters at the time, not long after storming out of the White House.
It was not the first time Mr. Trump had appeared to underestimate Ms. Pelosi, an older woman who spoke haltingly and gesticulated wildly, but who also held a sure-handed grip on her caucus and displayed an unshakable faith in the power of the institution she represented and the righteousness of her political positions.
And in every public interaction between the two, Ms. Pelosi seemed not only unintimidated, but also permanently appalled and deeply unimpressed by Mr. Trump.
Whenever Ms. Pelosi interacted with Mr. Trump, one could always see the strict mother of five who once ordered her children to make their lunches in an assembly line in order to get them to school on time.
Even her children shuddered at the memories.
After Ms. Pelosi offered Mr. Trump a patronizing clap during his State of the Union address in 2019 — a moment that created another memorable image, with Mr. Trump gazing up at Ms. Pelosi in what looked like a bid for her approval — her daughter Alexandra Pelosi said she recognized the gesture and bemused smile from times in her teenage years when she had misbehaved or miscalculated.
It meant that “frankly she’s disappointed that you thought this would work,” the younger Ms. Pelosi said.
Other times, Ms. Pelosi was not just disappointed, she was openly displeased. In 2020, she showily ripped up Mr. Trump’s State of the Union speech just after he finished delivering it, a moment that drew as much attention as anything he had said that night.
As the stakes grew higher, so did Ms. Pelosi’s hostility to the president.
When she plotted how to protect lawmakers and staff and return to the Capitol to certify the election results during the mob attack on Jan. 6, 2021, she referred to Mr. Trump as a “domestic enemy in the White House.”
Ms. Pelosi’s horror at what Mr. Trump was capable of might have grown over the years. But the power dynamic between them was set during their first Oval Office meeting in 2018, after the midterm elections when Mr. Trump was still learning the ropes of the job and Ms. Pelosi had not yet been re-elected speaker after Democrats won back control of the House.
Ms. Pelosi and Senator Chuck Schumer, Democrat of New York and the minority leader, were at the White House to discuss a potential government shutdown. Vice President Mike Pence was there, too, but all other players quickly faded into the background as the sparring between Ms. Pelosi and Mr. Trump took center stage.
Mr. Trump had sought to rattle Ms. Pelosi by keeping the cameras rolling on a meeting that was supposed to have been held in private.
But Ms. Pelosi taunted the president.
“Then do it,” she said, challenging him when he claimed that House Republicans could pass a spending bill that included funding for the border wall he was demanding. She interrupted him. And when Mr. Trump tried to undermine her by claiming that it was “not easy for her to talk right now” because she was still locking up the votes in her caucus to win the speakership, she delivered a line likely to make the history books written about Mr. Trump’s first term.
“Mr. President,” she said, “please don’t characterize the strength that I bring to this meeting as the leader of the House Democrats, who just won a big victory.” (She left the meeting with pep in her step, wearing sunglasses and a swishy red coat, captured in another photograph that later became a meme.)
Drew Hammill, a former top adviser to Ms. Pelosi, recalled watching that scene in the Oval Office unfold from a closet in the White House, where he and other staff had been told to wait.
“He never knew how to handle her — still doesn’t,” Mr. Hammill said. “She would always jujitsu the situation.”
Despite her ability to gain the upper hand with Mr. Trump, the president has continued to rise in power while Ms. Pelosi has stepped back.
In 2022, Ms. Pelosi announced she would not run again for leadership, making way for a new generation of House Democrats to take over.
On Thursday, she announced she would not seek another term, ending her history-making 39-year career in Congress. Ms. Pelosi has enjoyed her emeritus status in the House, often sitting in the cloak room eating hot dogs with her longtime female friends in the House.
But her revulsion toward Mr. Trump has never cooled. Just days ago, Ms. Pelosi described Mr. Trump in an interview with CNN as “the worst thing on the face of the Earth.”
The president returned the sentiment, telling Fox News on Thursday that her retirement was “a great thing for America,” and calling her “evil, corrupt and only focused on bad things for our country.”
Ms. Walsh said that, ultimately, Ms. Pelosi drew her power from the fact that she was not afraid of the president.
“At the end of the day,” she said, “what could he do to her?”
In footage of the Jan. 6 mob attack captured by her daughter for a documentary entitled “Pelosi in the House,” Ms. Pelosi made that clear. As staff members informed her that Mr. Trump was considering coming to the Capitol himself, Ms. Pelosi replied that she would be ready to take him on if he did, no matter the personal consequences.
“I’m going to punch him out,” she said. “And I’m going to go to jail, and I’m going to be happy.”
Annie Karni is a congressional correspondent for The Times.
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