Timing is everything in political life. Knowing when to run and when to call it quits is not only a skill for politicians but a test of character, requiring a dose of humility and an understanding that the arc of history is not a rainbow for those who overstay their welcome.
Nancy Pelosi, the first and only woman to serve as speaker of the House (twice), seems to have been keenly aware of this fact in announcing her retirement Thursday. With fresh challengers in state Sen. Scott Wiener and progressive tech millionaire Saikat Chakrabarti already in the 2026 race, Pelosi’s decision to make her 20th term in Congress her last has Democratic Party politicos publicly applauding — and some privately exhaling in relief.
“I think it’s really smart to do it now, because she has a year left in office, and there is plenty of time for [election] contenders to duke it out,” said Elizabeth Ashford, a California political strategist. “She’ll eventually put her finger on the scales, but you don’t want to get into a thing where the only question people are asking is, ‘When are you going to retire?’”
Fears of Pelosi, 85, faltering in the coming years have increasingly been a topic of conversation in San Francisco’s political scene. No one wanted to see her deteriorate in the way President Joe Biden did, or in the manner of the late U.S. Sen. Dianne Feinstein or Supreme Court Justice Ruth Bader Ginsburg. (opens in new tab)
Pelosi would know better than most how such selfishness can tarnish a legacy. She was instrumental in pushing Biden off the presidential ticket (opens in new tab) after a ghastly debate performance, but the action came too late to stop Donald Trump and Republicans from taking control of the White House and Congress. Meanwhile, dying in the chair spoke less to Feinstein and Ginsburg’s devotion to their jobs than to stubbornly going out on their own terms. The decisions by all three did lasting damage to their legacies and the Democratic Party.
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Jason McDaniel, an associate professor of political science at San Francisco State University, said Pelosi’s decision appears to be less of a selfless act than “a deft reading of the political environment.”
“I do think these last two years have shored up Pelosi’s legacy,” he added. “Not only has she avoided any embarrassing lapses akin to Feinstein or Biden, but she managed to be the prime mover in the Democratic Party’s efforts to replace Biden with Kamala Harris. I am not sure that would have happened without Pelosi’s leadership.”
Pelosi counted votes and fundraised with the best of them during her time in party leadership, and she remains sharp. (Also pointed: her reaction to a reporter’s question about Jan. 6 that she didn’t appreciate: “Shut up!” (opens in new tab)) But there is no denying that she has slowed since giving up her party’s leadership position in 2022. She suffered a bad fall last winter that led to hip replacement surgery, and she seems haunted by the vicious home invasion that nearly killed her husband three years ago.
Iconic moments — like Pelosi wielding the gavel after passing the Affordable Care Act, mini-clapping for Trump during a State of the Union speech in 2019, and strutting out of the White House in sunglasses and a brick-red coat after a contentious 2018 meeting — feel like distant memories.
But in recent months, Pelosi has been more present, holding events to speak out on the Republican tax breaks that sparked the protracted government shutdown. She helped raise millions of dollars in the Proposition 50 gerrymandering fight. Her retirement announcement is being framed as her going out on top after once again besting Trump and Republicans.
“When it comes to California political history, there are very few people — man or woman — who can hold a candle to Nancy Pelosi,” said Lorena Gonzalez, president of the California Labor Federation.
Pelosi defiantly told CNN this week that she would easily coast to reelection if she sought another term. “I have no doubt that if I decided to run, I would win,” she said. “That isn’t even a question.”
A more valid question could be: How many San Franciscans wanted that? At a crucial moment in which voters are demanding new ideas and fresh faces from the Democratic Party, Pelosi’s retirement paves the road for the future while preserving her status as the most powerful woman in U.S. political history.
Kim Nalder, a political science professor at Sacramento State University, noted that Pelosi is known for her strategic thinking and likely had Tuesday’s victories in mind — including Zohran Mandani’s meteoric rise to become mayor of New York City — when making her decision.
“She may have been looking at Tuesday night’s results in New York and seeing all of this momentum for younger, fresher faces in the party,” Nalder said. “That has been building for some time, but it feels like that wave is cresting.”
Jon Fleischman, a former executive director of the California Republican Party, said Pelosi’s retirement seems to be timed with handpicking her successor. Recent appearances featuring Pelosi and Supervisor Connie Chan, a progressive Democrat, have raised speculation that a campaign announcement and endorsement could be in the works.
“I think that is Pelosi’s chosen successor,” Fleischman said. “With [Wiener and Chakrabarti] in the race, she needed to give her chosen successor time to raise money. If she had retired two or four years ago, she could have really handed off the baton in style.”
And yet, Fleischman acknowledged, Pelosi has been a winner, and winners get to write their own story.
“The passage of Prop. 50 gave her the ultimate ability to say that she’s retiring at the height of her success,” he said. “It’s the final partisan coup de grâce at the end of a long career.”