Will she or won't she? Retirement hovers over Nancy Pelosi and her city

San Francisco: Nancy Pelosi flicked her hand like she was shooing away a gnat.

She had just been asked whether she was concerned about her new challenger in next year's election to represent San Francisco in Congress. His name, Saikat Chakrabarti, is unfamiliar to many of the city's voters. But it's one that gets under Pelosi's skin, given the tense history between the two Democrats going back to his brief and contentious time on Capitol Hill.

"I have them every time," she said of challengers as she made the hand flick.

Then came an even peskier question. Will this term in Congress -- her 20th -- be her last?

"I didn't come here to talk politics," she snapped. "When I'm in a political arena, I'll have an answer for you. But that doesn't worry me one bit."

Then, turning to members of her staff as they escorted her out of a San Francisco media event, she asked, "Why do they always give women the dumb questions?"

The subject is not as dumb as she might think.

For voters and political insiders in California and beyond, the question of whether she will or she won't when it comes to her retirement is having a moment. No one knows the answer for certain, but everyone seems to have an opinion on the pros and cons, and the implications, either way.

Pelosi has been representing San Francisco in Congress for more than 37 years, having first been elected in 1987. Locally, she is not so much a political figure but an era unto herself. She'll be 86 when her current term expires and has lately been recovering from a December fall, on the marble staircase of a palace in Luxembourg, that required emergency hip replacement surgery.

Her age, her health, the loss of her role as speaker of the House and the generational clashes between her party's young and elder leaders had led many to anticipate a retirement announcement.

Then along came Chakrabarti, the metaphorical gnat.

Chakrabarti is a progressive firebrand who helped pluck Rep. Alexandria Ocasio-Cortez out of a job as a New York City bartender and get her elected to Congress. And he has aired sharp criticisms of Pelosi on social media, alienating much of the elected Democratic Party in the process. He aims to bring the nationwide fight among Democrats over how to combat President Donald Trump home to San Francisco.

"I just realized the Democrats weren't actually changing at all," Chakrabarti said in an interview. "They're still obsessed with this seniority culture, relying on a backlash to Trump and hoping the pendulum swings back their way."

In 2018, after Chakrabarti helped Ocasio-Cortez win a seat in Congress as her campaign manager, he served as her chief of staff. He soon outraged moderate Democrats in Congress with a storm of social media posts condemning their support of an emergency border funding bill that he said did not fully address conditions in detention centers.

He tweeted that Democrats were "hell bent to do to black and brown people today what the old Southern Democrats did in the 40s." He also singled out Pelosi, arguing that she was not willing to talk about the impeachment of Trump but was also not doing much to help working-class Americans either.

"What is this legislative mastermind doing?" he tweeted.

The comments were considered a huge breach of decorum, and rank-and-file Democrats demanded his ouster as Ocasio-Cortez moved to make peace with the Democratic caucus. Shortly after a closed-door meeting between Pelosi and Ocasio-Cortez, Chakrabarti left his job.

Chakrabarti, 39, has plenty of cash to spend. He was the third employee at Stripe, a payment processing company, and has said he's worth hundreds of millions of dollars and is willing to spend a chunk of his fortune on his campaign.

Pelosi has filed a statement of candidacy for 2026, a formality that allows her to raise money, but has not explicitly said she will run -- or that she will not. Even her closest allies do not know her plans.

Her spokesperson declined to comment about her decision on retirement.

Eric Jaye, a longtime San Francisco political consultant who worked on Pelosi's first campaign, said that he had no doubt she would beat Chakrabarti, but also that it would be contentious enough that she might decide to skip it.

"I think she's going to retire, and it's a moot point," Jaye said. "I seriously doubt she would want her legacy, as stellar as it is, tarnished by having her last race needing to be a knockout, drag-out, negative fight with a representative of the next generation of leaders."

"I doubt she has any appetite for that," he continued. "And she has nothing left to prove."

Drew Hammill, a political strategist who worked for Pelosi from 2006 to 2023, said he did not know what the former speaker's plans were but that she would certainly not base her decision on Chakrabarti's candidacy.

"The furthest thing from her mind after the weather in the South Pole is this kid," he said.

But it is possible Pelosi would be in a tighter race than some political insiders expect.

Interviews with a dozen people on the streets of San Francisco on Thursday showed a range of attitudes toward Pelosi, from indifference to a desire to see her retire. While several residents said they appreciated her decades of service, they also said they were ready for change.

Nickolas Saldivar, a 44-year-old commercial real estate broker, said he did not feel represented by Pelosi and her Democratic colleagues in Congress as Trump dismantles the federal government.

"I think that there's young blood that needs to come out and that's going to reinvigorate the party in general," he said as he stood on Mission Street. "Most of the elected officials, including Pelosi, have been pretty silent on what's been taking place in D.C."

Liz Boder, an artist and vendor near the downtown cable car turnaround, said she was "a little bit 50/50 on it" when asked if Pelosi should retire. She said that the former speaker's career had been phenomenal but that it might be time for someone new.

"She's had health issues, and she's getting a little older, and we might want some fresh perspectives in there," she said.

Pelosi visited a San Francisco hospital Tuesday to discuss the importance of preserving Medicaid amid Trump's slashing of the federal budget. She walked slowly, but without the ski poles she had been leaning on until recently. She has ditched her trademark heels for flat, fuzzy clogs.

In addition to her fall, she has dealt with family issues. Her husband, Paul Pelosi, who was viciously attacked in 2022 in the couple's home by a right-wing conspiracy theorist, recently required a kidney transplant. The organ was donated by their daughter, Jacqueline Pelosi.

In addition to Chakrabarti's challenge from the left, Pelosi would most likely have a deep-pocketed opponent on her right.

David Brailer, the chief health officer of the Cigna Group, a global health insurance company, said he was "strongly considering" entering the race. He declined to discuss details, but a person familiar with his thinking said Brailer was already conducting polling and was prepared to spend at least $10 million of his own health-care-related fortune on his campaign.

Brailer is not registered with either party and said he believed voters were tired of both Democrats and Republicans and wanted "pragmatic problem solvers."

One of the strongest potential challengers for the former speaker would be state Sen. Scott Wiener, who has collected nearly $1 million in an exploratory committee to fund a race for the seat he has openly coveted for years. He has won support from a wide variety of voters, including many in the LGBTQ+ community.

But Wiener has pledged to not run until Pelosi retires and said he would not run in 2026 if her name was on the ballot. He declined to comment other than to say it would "be an honor" to succeed her.

Another daughter of Pelosi's, Christine Pelosi, a lawyer who is active in the Democratic Party, has long been considered a likely heir apparent, although she is staying as tight-lipped as her mother about her own plans.

"My plans are to celebrate Women's History Month and make sure the 15th anniversary of the Affordable Care Act is not the last!" she texted Tuesday in response to a request for comment.

Jaye said he expected Nancy Pelosi to announce her retirement with enough time left in her term to work toward a win for her daughter -- or for Wiener, if her daughter opted not to run.

Whoever is his main challenger, Chakrabarti said he believed voters were ready to dump traditional, moderate Democrats in favor of progressives.

"I think we're in an existential moment for the country," said Chakrabarti, who worked on Sen. Bernie Sanders' 2016 campaign for president. "How are we going to rebuild from this mess?"